easy and less easy mushrooms

Posted on February 2, 2015 by admin

These are a few of what occurs here and were encountered this past Winter.

Chanterelles, hedgehogs and shaggy-manes are easy and almost foolproof mushrooms. (Although I agree with Douglas Adam’s warning not to “underestimate the ingenuity of complete fools“.)

Chanterelles potentially do have some look alikes but there are none that will confuse anyone who pays attention to details. If the gills are narrow, deep and nicely-defined, it is not a chanterelle.

Several different chanterelles live here. The last several winters have been lacking adequate rain so all of those chanterelles have been few and far between.

This is the only decent golden chanterelles that I found this entire Winter. (I also found a single white chanterelle but the images did not turn out.)

Cantharellus in habitat in Mendicino County; litter is tan-oak occurring amidst doug-firs

Cantherellus

Cantharellus

These have long beeen known as Cantharellus cibarius but research is revealing that one to be a strictly European species and the multiple Cantharellus species occurring on the Pacific Coast and elsewhere are now being identified and named. (Michael Kuo has a nice page about this.)

Hedgehogs had a slightly better year but it was not great. These have caps that occur in a range of colors from creamy to orange. The teeth and stem are typically whitish and stain orange with age or damage.

This is an easy one with no poisonous look-alikes. Any of the truly inedible Hydnum species are also extremely unpalatable in taste and look quite different.

Hydnum repandum

These are sweet and delicious with a really fine texture but they cause me to produce enough gas internally to potentially fuel the needs of a small community so I avoid eating them.

Shrimp Russulas are also potentially fairly easy — assuming that a person has a mind for details. Errors are quite possible if not.

These are not my favorites, the flavor is fine when they are young but I do not care for the texture of Russula species in general. They are OK in a pinch.

Russula xerampelina

Prince Agaric (Agaricus augustus) is awesome in almost every way (taste, texture, aroma and appearance) and this species had an above average year here. They also tend to fruit alongside roads and near other human activity. They are known to be heavy metal accumulators of lead and cadmium so I do not eat many of them.

This species has some potential look-alikes but those have pink gills when mature (gills on this one are dark brown when mature) or they have a different spore color or they have a foul smell.

Agaricus augustus working out with some weights

Agaricus augustus

I almost wish that these were not so damn delicious. They remind me a lot of a portabello someone smothered with almond-extract. Flies target this one really fast so it needs to be harvested and either eaten or refrigerated as soon as possible after it comes up. The one below is older than ideal for that reason.

Agaricus augustus

This species typically fruits here from dew-fall during the normally dry month of June but for whatever reason they have fruited intermittently through all of last summer, fall and winter following periods of rain.

Shaggy-manes (Coprinus comatus) are very easy to recognize but turn to weeping ink rather quickly. This is among the nicest of the edible mushrooms but is known to be an indicator of arsenic-containing soils. As it is known to accumulate arsenic and other heavy metals this one is best enjoyed infrequently.

Coprinus comatus

a rain-beaten Coprinus comatus

inside of Coprinus comatus

Waxy caps (Hygrocybe sp.) are considered to be edible but are also known to be heavy metal accumulators, the gorgeous red and yellows apparently come from cadmium, so they are not a good choice for food. They also are not particularly exciting in either their flavor or their texture.

Hygrocybe sp,

Hygrocybe sp.

Acacia berlandieri

Posted on January 15, 2015 by admin

Senegalia berlandieri (Bentham) Britton & Rose

George Bentham 1842 London Journal of Botany, 1: 522, as Acacia berlandieri.
Nathaniel Lord Britton & Joseph Nelson Rose 1928 North American Flora, 23: 109, as Senegalia berlandieri.

This is still most often referred to in plant databases as Acacia berlandieri.

Synonyms of note: Acacia emoryana Bentham

Etymology:
Acacia Merriam-Webster gives as derived from the Greek akakia referring to a “thorny Egyptian tree,” adding it is perhaps related to the Greek word ake meaning “point” or “thorn”.
Senegalia is unclear in its intended reference, as it was not explained when it was published, but is thought to be from “gum senegal” which is a high-quality Acacia gum.The name itself was obviously derived from the African nation of Senegal.
berlandieri was named to honor Jean Louis Berlandier, a French naturalist & botanical explorer, who collected this species.

Common names:
“Guajillo” “Berlandier’s Acacia” [See Endnote A]
guajillo: Spanish; juajillo: Mexican; hujilla: French; (Parks 1922).
With many variant spellings. [See Endnote B]

Occurrence & Distribution:
Monterey, Nuevo León. Southern Texas to Tamaulipas and Querétaro (Britton & Rose 1928); Texas into Chihuahua (USDA); Rio Grande Plains of south Texas and Tamaulipas northwest along Rio Grande into eastern Brewster County, Texas, and southeastern Chihuahua; south through Coahuila and northeastern Durango to San Luis Potosí, Querétaro, Hidalgo, and Veracruz, Mexico (UTEP); Brewster, Terrell, Val Verde, also continuing and abundant along the Rio Grande Plains, rarer in the deep soils of the Rio Grande Valley and Delta. Occurring as far north as the southern Edwards Plateau and in Mexico from Coahuila south and east to Querétaro and Veracruz (Powell 1998).

Habitat:
Thorny brush country. Grows abundantly in many dry soil types, including limestone, caliche and gravels, occurs in coastal prairie, abundant in South Texas plains on limestone ridges and cuestas, southern Edwards Plateau and in the Trans-Pecos but it is most prolific in shallow soils and on ridges. “Brush country on rocky hills, slopes or flats, limestone outcrops, often with mesquite-oak or cactus-mesquite“, (Isely 1969). Does best in full sun but can tolerate partial sun.

Original description:
“inermis, ramis petiolis inflorescentiaque cano-tomentosis, pinnis 10-12-jugis, glandulis depressis, foliolis 30-50-jugis linearibus obtusis supra opacis glabris v. tomentellis subtus pubescentibus subcanescentibus, panicula terminale incana, capitulis parvulis dense multifloris cano-pubescentibus, calyce corolla parvum breviore. Habitu A. Langsdorffi affinis. Foliola vix 2 lin. longa. Flores in specimine omnes masculi videntur. Petala basi libera, medio connata. Stamina numerosa. Monterrey, Texas.”
Bentham 1842, p. 522.

Description:
A small semi-evergreen bipinnate small tree or shrub, 3-4.5m tall (sometimes larger with irrigation) and often growing as wide as it is tall.
The many white-tomentose trunks arise from a stubby root with a very deep root system.
The plant may be relatively unarmed or may be prickly with scattered curved small spines.
The long, slender stems bear only a few branches, mostly on one side.
Foliage is green to gray-green, soft, lacy and from a distance is almost fernlike in appearance. Petiolar gland is sessile; stipules small, caducous; pinnae as 10-12 pairs; small leaflets in 30-50 pairs, linear, 4 mm. long, tomentose, becoming glabrate; peduncles axillary, sometimes in pairs or in leafy racemes, pubescent, 2-5 cm. long;
Fragrant small flowers in dense round clusters to 1.5 cm, creamy-white to yellow; Calyx 5-lobed, the lobes valvate, Corolla 5-lobed, calyx and corolla pubescent; Stamens are many and distinct, the yellow anthers are small; Ovary is densely white-lanate;
Fruit is a reddish (when ripe) dehiscent legume, 1o-15 cm. long, 1.4-2.5 cm. broad. It is compressed, flat, thin, tomentose and somewhat turgid when ripe. Its valves are chartaceous or coriaceous. The young legume is white.
5-6 light brown seeds.
Adapted from Britton & Rose 1928, Isely 1969, Park 1922, Richardson & King 2011, & Van Dersal 1938.
[Botanical glossary]

Chromosome number 2n = 26 (Isely 1969 cited Turner 1959 Legumes of Texas.)

Flowering:
March through May, Isely 1969; March, April, May & June, Ladybird Johnson Wildflower Center; November through March, Van Dersal 1938.

Seed collection:
Late summer through early fall (Ladybird Johnson Wildflower Center), “available June-July” (Van Dersal 1938).

Zone:
8 -11 (USDA)

Soils:
Rocky limestone, calcareous gravelly-loam, sandy, silt and clay soils.

Uses:
Ornamental shrub, erosion control and widely regarded as producing a superior quality honey that may be pale or “water white” (Parks 1922).
Used by the Long-tailed Skipper (Urbanus proteus) as a larval host and nectar source, Ladybird Johnson Wildflower Center.

Other:
Prefers full sun and dry soils. Tolerant of high heat and cold to 10°F. Seeds are said to need scarification or acid soak.

Published analysis
(Shares a page with Acacia rigidula.)

Controversy:
Data integrity of the published analysis in Clement et al 1997 has been called into question.

Images
(Shares a page with A. rigidula.)

References & online information resources:

Bentham, George (1842) London Journal of Botany, 1: 318-392, 494-528, “Notes on Mimoseae, with a synopsis of species.”

Britton, Nathaniel Lord & Joseph Nelson Rose (1928) North American Flora, 23 (2): 1-194, “Mimosaceae”.

Clement, B.A. et al. (1997) Phytochemistry, 46 (2): 249–254. “Toxic Amines and Alkaloids From Acacia berlandieri.” (Beverly A. Clement, Christina M. Goff & T. David A. Forbes)

Isely, Duane (1969) SIDA, 3 (6): 365-386. “Legumes of the United States. I. Native Acacia.”

Martin, Chris A., Virtual Library of Phoenix Landscape Plants Arizona State University: http://www.public.asu.edu/~camartin/plants/Plant%20html%20files/senegaliaberlandieri.html

Merriam-Webster Dictionary online http://www.merriam-webster.com/

Parks, H.B. (1922) American Bee Journal, 62: 414-414. “Agaria, Guajillo and Mesquite.”

Powell, A. Michael (1998) Trees and Shrubs of the Trans-Pecos, pp. 166-167.

Richardson, Alfred & Ken King (2011) Plants of Deep South Texas.

Shulgin, A.T. “Sasha” (2001) Dear Dr. Shulgin, at CCLE (Center for Cognitive Liberties & Ethics) [http://www.cognitiveliberty.org/shulgin/adsarchive/acacia.htm]

TAMU Plants of the Texas Rangelands (A&M University) http://essmextension.tamu.edu/plants/plant/guajillo/

USDA Plants Database http://plants.usda.gov/core/profile?symbol=ACBE

UTEP (University of Texas at El Paso) http://museum2.utep.edu/chih/gardens/plants/RtoS/senegaliaberlandieri.htm

Van Dersal, William R. (1938) Native Woody Plants of the United States, Their Erosion-Control and Wildlife values. USDA Misc. Publ. 303.

Ladybird Johnson Wildflower Center http://www.wildflower.org/plants/result.php?id_plant=ACBE

Endnotes on “common names”

Note A: A comment seems to be in order concerning the name Berlandier Acacia / Berlandier’s Acacia.
Unless there is evidence to the contrary, I have grown to distrust the actual historical legitimacy of most of the common names that appear to be direct English conversions of Latin binomials. Berlandier’s Acacia MAY be a good common name but it can be readily noticed that the vast majority of these names arose when botanical database compilers in the USDA and other governmental agencies who were creating plant databases perceived a need for common names where they were lacking It could be justly said that those are now common names but I’d suggest that to be legitimately considered a common name, that name should actually already be in common use by someone before appearing in print.
In the case of Berlandier Acacia I can presently only track the use of this name back to around 1970 when it appeared in USDA plant species listings. Earlier publications, including those from USDA (such as Van Dersen 1938), do not appear to include the name. Information to the contrary is welcomed.

Note B: Guajillo, the most common name, has had many origins proposed.
The most accurate one, even if broad, appears to be that it is a diminutive form of the Mexican word guaje (derived from Nahuatl uaxin) which has several meanings.
Guaje can variously mean, a boy or youth, a gourd, “foolish”, “silly”, and a species of Acacia [in reference to what is now called Leucaena esculenta], (from El Diccionario de la lengua española) It is also the name of a chili pepper.
Guajillo has been suggested to be a Spanish word variously presented as meaning “big pod” and “little gourd”. Most of those two translations involve the chili pepper with this name rather than the Acacia.
The translation as “big pod” appears many places, for example in Scott Linquist & Joanna Pruess (2007) Mod Mex: Cooking Vibrant Fiesta Flavors at Home, but does not appear to make sense.
I have not yet located the actual initial appearance of “little gourd” as a definition but I did find it interest that the sentence “Guajillo means “little gourd” for the rattling sound the seeds make in dried pods” can be found reiterated on 260 primarily seed-vending websites with little to no variation. The “pod” in that sentence also refers to the Capsicum fruit not that of the Acacia.
Guaje is also a well known southern Mexican and Guatemalan plant (now Leucana esculenta) which similarly can become increasingly toxic to the browsing animals that choose it so guajillo may have been coined in reference to it looking very similar but with much smaller leaflets.
Parks 1922 creatively suggested it to possibly be derived from aguajillo and to be connected to water in some way. Parks offered aguajillo as possibly meaning “little water jug” for the sake of the leaves capturing and holding dew, or, possibly, “little water” to reflect it tending to grow in dry places. Both are inaccurate despite making true statements.
Parks’ speculation about the word guajillo and the plant holding water amidst the structures of the leaves does contain an interesting observation even if it appears baseless as a suggestion for the etymology.

Acacia berlandieri after a rain

Acacia rigidula

Posted on January 14, 2015 by admin

Vachellia rigidula (Bentham) Seigler & Ebinger

George Bentham 1842 London Journal of Botany, 1: 504–505, as Acacia rigidula.
David S. Seigler & John E. Ebinger 2006 Phytologia, 87: 166, as Vachellia rigidula.

This is still most often listed in databases and indexing services as Acacia rigidula.

Synonyms of note: Acacia amentacea DC is common as a synonym. (De Candolle 1825 Prodromus Systematis Naturalis Regni Vegetabilis, 2: 455) [Endnote A]
Britton & Rose 1928 North American Flora, 23 (2): 94, described as Acaciopsis rigidula.

Etymology:
Acacia Merriam-Webster gives as derived from the Greek akakia referring to a “thorny Egyptian tree,” adding it is perhaps related to the Greek word ake meaning “point” or “thorn”.
Acaciopsis means that it looks like an Acacia.
Vachellia “This name honors Reverend G. H. Vachell who collected extensively in China“, Seigler & Ebinger 2006
rigidula is in reference to something being rigid. Bentham probably was referring to the branches. Both the spines and the branches are rigid.
amentacea means “in the form of a catkin” in reference to the flower spikes. according to Stearn (catkin = Amentum).

Common names:
“black brush” (blackbrush/black-brush), “gavia” (Tamaulipas), “chaparro prieto” (Nuevo León, Tamaulipas) [Endnote B]
“Black bush” can also be found listed but should be suspected to be the result of a typo.

Occurrence & Distribution:
Britton & Rose 1928 give as “Southern Texas to Tamaulipas, Nuevo León and San Luís Potosí.” Powell 1998 notes as occurring in northern Mexico to SLP and Tamaulipas, to be abundant in the Rio Grande Plains and through South Texas, also to be common in Val Verde County (1100–1800 ft), occurring in Terrell County, and also more rarely farther West in Brewster County close to the Rio Grande. UTEP: “South Texas and adjacent Tamaulipas, northwest along the plains of the Rio Grande corridor into southeastern Trans-Pecos and south through Coahuila, Nuevo León to San Luis Potosí and Veracruz“.

Habitat:
Dry soils including rocky limestone, calcareous gravelly-loam, loamy, sandy and clay soils. Often found on limestone caliche ridges, slopes, hillsides and canyons. It is a common component of the thorny brush-country of South Texas. Powell 1998, TAMU, UTEP.

Original description:
“glabra, ramis flexuosis verrucosis, spinis rectis subulatis, pinnis unijugis, petiolo brevi, glandula scutellæforme, foliolis 4–5-jugis obovati-oblongis obtusis mucronatis coriaceis venosis, spicis cylindricis laxis breviter pedunculatis folio longioribus. Spinæ nunc 1–2-lin. sæpius 6-lin. longæ, interdum pollicares. Foliola 4–5-lin. longa, penninervia. Spicæ pollice longiores. Flores sæpius 4-meri.”
Benson 1842, pp. 504-505.

Description:
Perennial deciduous thicket-forming shrub or small tree, 3–4.5 meters high (UTEP gives as 3′ to 15′ H by 3′ to 12′ W), many long branches arising from a central trunk.
Branches are stiff, commonly zigzagging, with pairs of short, straight and very sharp spines, 0.5-2.8 cm long, sometimes growing up to 5 cm. long. The spines are placed at the base of each petiole (stipular).
Leaves are dark green and bipinnate with “mostly” 1 pair of glabrous pinnae; there are 3–6 pairs of oblong leaflets, 6–15 mm long, the leaflets are obtuse, apiculate and often shining/lustrous, the petiole and rachis are also glabrous and the petiole is gland-bearing;
Inflorescence is axillary with persistent bractlets, small sweetly-fragrant whitish to pale-yellow flowers in short, slender sessile spikes 2–3(–5) cm. long; stamens are numerous, distinct and short;
Fruit is a narrow, curved, flat legume 6–8 cm. long (up to 3-1/8″ long according to Richardson & King 2011), 3-4mm wide. Fruit is 2-valved, with divisions between seeds, readily dehiscent, the valves separating into 2 layers, and covered with minute hairs (puberulent). Black, brown or reddish.
Seeds are oblong, lenticular, their axis parallel with the legume, the funiculus is long. Reddish-brown when ripe.
Adapted from Britton & Rose 1928, Isely 1969, Richardson & King 2011, Stanley 1922, TAMU & UTEP.
[Botanical glossary]

Chromosome number 2n = 26 (Isely 1969 cited Turner 1959 Legumes of Texas)

Flowering:
(Feb.) March, April, May & June. Beginning in Spring before leaves have fully appeared. Isely 1969, Wildflower Center & UTEP. March-April and following rains is a common pattern.

Seed collection:
Late summer through early fall when fully ripe. Wildflower Center.
A seed photo is at the USDA website.

Zone:
Said to be hardy to 20°F (UTEP). It is clear that they survive colder temperatures in the wild.

Uses:
Ornamental shrub, thorny barrier hedging, erosion control and renown as a superior honey source. “This tree provides fair grazing for wildlife and poor grazing for livestock“, UTEP.

Other:
Fairly slow growing, responds well to pruning, does best with partial shade.

Published analysis
(Shares a page with Acacia berlandieri)

Controversy:
1) Diet aids claimed to contain this compound were reported to contain one or more non naturally-occurring amphetamine. (See Pawar et al. 2014) It was suspected this plant may have been chosen as a masking agent to disguise the true nature as being synthetic stimulant additives. No amphetamine of any type could be observed in their samples of the actual plant materials. Known natural sources of amphetamines (such as ephedrine) were also included in some of the formulations such as Ephedra and Sida but they were found to contain synthetic molecules lacking naturally known sources. (See a number of examples of product labels in Cactus Chemistry By Species.)
2) Published analysis by Clement has been accused of being non-reproducible. (See Pawar et al. 2014) Comments by Shulgin are also noteworthy.
[See Analysis overview.]

Images
(Shares a page with A. berlandieri)

References & online resources:

Bentham, George (1842) London Journal of Botany, 1: 318–392, 494–528, “Notes on Mimoseae, with a synopsis of species.”

Britton, Nathaniel Lord & Joseph Nelson Rose (1928) North American Flora, 23 (2): 1–194. “Mimosaceae”.

Clement, B.A. et al. (1998) Phytochemistry, 49 (5): 1377–1380. “Toxic Amines and Alkaloids From Acacia rigidula.” (Beverly A. Clement, Christina M. Goff & T. David A. Forbes)

Correll, Donovan Stewart & Marshall Conring Johnston (1970) Manual of the Vascular Plants of Texas.

Isely, Duane (1969) SIDA, 3 (6): 365-386. “Legumes of the United States. I. Native Acacia.”

Merriam-Webster Dictionary online
http://www.merriam-webster.com/

Pawar, R.S. et al. (2014) Journal of Pharmaceutical and Biomedical Analysis, 88: 457–466. “Determination of selected biogenic amines in Acacia rigidula plant materials and dietary supplements using LC–MS/MS methods.”

Powell, A. Michael (1998) Trees and Shrubs of the Trans-Pecos.

Richardson, Alfred & Ken King (2011) Plants of Deep South Texas.

Shulgin, A.T. “Sasha” (2001) Dear Dr. Shulgin at CCLE (Center for Cognitive Liberties & Ethics) [http://www.cognitiveliberty.org/shulgin/adsarchive/acacia.htm]

Seigler, David S. & John E. Ebinger (2006) Phytologia, 87: 139-178, “New combinations in the genus Vachellia (Fabaceae: Mimosoideae) from the New World.”

Stanley, Paul C. (1922) Trees & shrubs of Mexico, page 376.

Stearn, William (2004) Botanical Latin.

TAMU Plants of the Texas Rangelands (Texas A&M University)
http://essmextension.tamu.edu/plants/plant/blackbrush/

USDA Plants Database
http://plants.usda.gov/core/profile?symbol=ACRI

UTEP (University of Texas at El Paso)
http://museum2.utep.edu/chih/gardens/plants/TtoZ/vachelliarigidula.htm

Ladybird Johnson Wildflower Center website
http://www.wildflower.org/plants/result.php?id_plant=ACBE

Endnotes:

Note A: USDA gives Acacia amentacea DC as a synonym based on that opinion appearing in Stanley 1922. For that reason and the accepted rules of priority, prior to the creation of Vachellia rigidula it was not uncommon to find Acacia rigidula being absorbed into Acacia amentacea. This is a result of the perennial ebb and flow between the viewpoints of lumpers and splitters.
They were distinguished by Correll & Johnson 1970 who believed that “true” Acacia amentacea was limited in distribution to southwestern Mexico.
Isely 1969 considered the Mexican Acacia amentacea to be “almost identical except for fewer leaflets“.
Britton & Rose 1928 listed a number of relatively small differences: straight spines on rigidula versus acicular (needle-shaped) spines on amentacea, a longer maximum length of spines for rigidula (up to 5 cm compared to 1-2.5 cm for amentacea), fewer leaflets on amentaceae (2 pairs compared to 3-6 on rigidula – although it should also be noted that TAMU gives 1-8 for rigidula), the rachis on amentacea is said to be grooved and somewhat pilose as opposed to glabrous on rigidula, with leaflets 10-20 mm long on amentacea compared to 6-15 on rigidula.

Note B: “chapparo” is a Spanish word used for several trees. The Spanish word “prieto”, referring to a “dark-skinned person”, is increasingly falling into disuse in databases, perhaps as it is also commonly used as a derogatory term.

Acacia berlandieri & Acacia rigidula

Gallery

Please view this page at http://sacredcacti.com/blog/acacia/ .

It has been expanded.

Brush country on the Bordas Escarpment in Jim Hogg County, Texas
A. berlandieri is on the front left, and beyond, with A. rigidula on right

Questions & comments concerning the analysis of Acacia berlandieri & Acacia rigidula

Acacia (Senegalia) berlandieri (description & illustrations)
Acacia (Vachellia) rigidula (description & illustrations)

In 1997, and then again in 1998, some almost unbelievable news rippled awkwardly through the world of plant science. Methamphetamine had just been reported from two abundant Acacia species that were already well-known for producing alkaloids involved with livestock problems.
The new information was then echoed far more loudly and unquestioningly through the counterculture, and in a flurry of news reports, and by the indexers & assemblers of the various reference databases on phytochemicals and naturally occurring compounds. It soon began appearing in works on toxicology, plant chemistry and drug issues. [A very few examples: T. Garland & A.C. Barr (eds.) 1998 Toxic Plants and Other Natural Toxicants (with a chapter by Clement & Forbes), ‪G.E. Burrows‬ & ‪R.J. Tyrl‬ 2012 ‪Toxic Plants of North America‬, E. Eich 2008 Solanaceae and Convolvulceae: Secondary Metabolites, J.M. Hagel et al. 2012 Trends in Plant Science, 17 (7): 404-412, “Biosynthesis of amphetamine analogs in plants”, G.H. Rassool 2009 Alcohol and Drug Misuse, & ‪T.R. Kosten‬ 2012 Cocaine and Methamphetamine Dependence.]
Questions and conversations also rapidly proliferated in online discussions among people interested in drug abuse – both those with interests in its prevention and those who were interested in learning more about the possible potentials for human ingestion of the ‘new’ drug plants.
In the case of Acacia rigidula, this report also fueled a minor explosion of commercial weight-loss products that included this plant, at least in the list of ingredients on their label.

What made the news even more astonishing was that it was not just meth that was reported to be in those Acacia leaves, but also amphetamine and a handful of synthetic substituted amphetamines never before been observed in nature.
Other novelties making their first appearance as natural Acacia phytochemicals included a patented & FDA approved pharmaceutical, the tricyclic antidepressant Nortriptyline, and a putative neurotoxic agent, the synthetic fragrance molecule Musk ambrette.
They were further described to be accompanied by an almost bewildering array of amines. For some of the familiar alkaloids this marked their first report outside of the family Cactaceae. That included mescaline, trichocereine and four isoquinolines. All of which were reported to occur along with dopamine, candicine, dimethyltryptamine (DMT) and nicotine as part of the nearly four dozen compounds that were said to have been identified in the two Acacia species.
Simple phenethylamines, DMT and nicotine are well known from other Acacia species but the crazy pharmacological cocktail that was conjured in people’s minds by those two reports certainly stirred up a bit of attention from both the peanut gallery and from assorted professional interests.
See Endnote A at the bottom of this page for some search result numbers.

In a conversation occurring a year or so after the second publication had occurred, Sasha Shulgin questioned the soundness of my inclusion of the information in the 1999 printing of Cactus Chemistry By Species. Sasha brought to my attention some odd discrepancies concerning those two accounts by Clement. The first and most concerning to Sasha, despite repeated efforts apparently none of the authors had responded to his contact attempts. In Sasha’s mind, the failure of any professional researcher to respond to questions from one of their peers was a warning sign that problems existed for the report. Organic chemists typically welcome interest in their work being expressed by other organic chemists.

Sasha further claimed to have noticed that not all the novel compounds that their two papers purported were synthesized as reference materials have a published synthesis. Interest in learning more details about the synthetic work was Sasha’s reason for his contact attempts. He eventually went on to dismiss the results of both papers entirely, and in an online Q&A column Sasha joked that dirty, perhaps recycled, laboratory glassware might be a possible although unlikely culprit; “even in Texas“.
(See Dear Dr. Shulgin [http://www.cognitiveliberty.org/shulgin/adsarchive/acacia.htm] for his exact comments in 2001.)
More recent work resulting from interest by the FDA, published in Pawar et al. 2014, was unable to detect the presence of mescaline, mescaline derivatives or any of the purported amphetamines and isoquinolines. With only the exception of tryptamine & one of the four samples of bark showing a trace of N-methyltrypamine (neither of which are surprising for an Acacia species) none of the novelties reported by Clement were observed.
It did largely support the prior analytical work in the handful of papers previously published by Adams, Camp and coworkers but deviated by not finding N-methylphenethylamine to be the major alkaloid in any of their samples. Pawar found it to be lacking in half of their samples and present only as trace amounts in the other two.

The novel results in Clement’s accounts still need replication by someone.

Dr. Clement has commented about being unaware of any controversy or questions existing about their work but this appears to be in conflict with two professional workers (Dr. Shulgin & Dr. Terry) who voiced comments to me about their experiences with Dr. Clement while they were still trying to learn answers for the questions they noticed. An interview with Dr. Clement by Natural Products Insider in 2013, in which she defended their reported data and described the elaborate precautions that were said to be necessary in order to produce the same results. (Such as performing the extraction and solvent removal using the protection of an argon blanket.)

And to be fair to Dr. Clement, it is noteable that no one at FDA actually tried to replicate her work rather than apparently rejecting the precautions taken to prevent degradation as being unnecessary. I may agree with the conclusions of her critics but I would also suggest that, thus far, no one can legitimately claim that anyone actually attempted to replicate what was reported in Clement et al. 1997 and 1998. For the most part, Clement began by extracting fresh (1997) and fresh and still frozen (1998) plant materials, whereas Pawar et al 2014 freeze-dried their fresh plant samples. (Clement had used freeze drying of fresh frozen leaves for quantification of N-methylphenethylamine.) Pawar also omitted the use of argon which Clement presented as important to prevent degradation of alkaloids. However, Pawar’s interest was not an academic one trying to reproduce Clement’s results but rather was focused on establishing what compounds were in the diet products they also tested and whether those contents came from this plant. Their point of study really had no reason to respect the concerns voiced about the degradation of alkaloid content. And to be fair to her critics, Clement did not describe the needs for such protection within her two accounts with nearly the same amount of details as she did within that interview in 2013. (The pertinent comments from those papers as concerns argon can be found quoted farther below.)

In that interview (if you have not already done so, you might want to read it before continuing) there are a number of things the careful reader might notice are peculiar for sake of not being mentioned at all, such as their discovery of a wealth of novel Acacia alkaloids.
There are also some words included in that interview that are worth noticing:

“The early season guajillo was unremarkable to Clement and her team. “The extraction was clean (bright green extract, easily partitioned with acid and base extraction),” Clement reported. “The analysis was relatively straightforward; we found terpenes, a few simple phenols and scant traces of β-phenethylamine, but no detectable N-methyl-β-phenethylamine, which had previously been reported.” However, work on late season guajillo was a different story. “The initial methanol extract was a very dark green, almost black color,” she noted, adding the team realized these extracts had to be handled much more carefully due to extreme vulnerability to degradation. “After we began using an argon blanket, this degradation was no longer a problem; argon is a much more forgiving inert atmosphere than nitrogen.” The end result was positive identification of N-methyl-β-phenethylamine; N,N-dimethyl-β-phenethylamine; and tyramine in these fractions.”
INSIDER, November 26, 2013 written by Steve Myers.
Online at http://www.naturalproductsinsider.com/articles/2013/11/blackbrush-scapegoats-or-shaky-goats.aspx (Accessed on 17 May 2014; still online in January 2015)

Compare those comments to their results in the tables below. In particular, compare what was highlighted in bold (by me) in the text above & in the tables below (and compare her words above about the need for argon to the comments farther below under Clement et al. 1997, Clement et al. 1998, Clement & Forbes 1998, & Clement 2013).

Acacia berlandieri Bentham (these results need to be questioned)

Compound	Spring	Late fall
(all via gc-ms)	ppm	ppm
Phenethylamine	991.3	1390.0
N-Methylphenethylamine	1702.7	3742.2
N,N-Dimethylphenethylamine	99.1	604.4
N,N,N-Trimethylphenethylammonium hydroxide*	nd	23.6
Amphetamine	3.1	10.1
Methamphetamine	20.1	11.5
N,N-Dimethyl-α-methylphenethylamine	45.6	229.7
p-Hydroxyamphetamine	8.0	7.3
p-Methoxyamphetamine	nd	35.7
Tyramine	367.2	1263.4
N-Methyltyramine	188.5	745.7
Hordenine	9.2	333.1
Candicine*	nd	35.1
Dopamine	3.6	25.3
N-Methyldopamine	1.9	10.8
N,N-Dimethyldopamine	nd	nd
3-Methoxytyramine	2.6	15.3
Mescaline	4.9	35.7
N-Methylmescaline	3.2	30.2
Trichocereine	nd	28.1
3,4,5-Trimethoxyphenethyl-N,N,N-trimethylammonium hydroxide*	nd	13.2
3,5-Dimethoxytyramine	2.7	43.4
3,4-Dimethoxy-5-hydroxyphenethylamine	11.4	40.9
β-Methoxy-3,4-dihydroxy-5-methoxyphenethylamine	nd	30.2
3,4-Dimethoxy-α-methyl-5-hydroxyphenethylamine	2.0	47.2
Nicotine	39.6	108.3
Nornicotine	19.2	72.5
Anhalamine	4.9	39.6
Anhalidine (N-Methylanhalamine)	2.9	40.9
Anhalonidine	2.7	46.8
Mimosine, methyl ester	10.6	24.2
3α-Cumyl-1,3,4-oxadiazolidine-2,5-dione	308.4	420.9
Nortriptyline	19.8	71.5
Musk ambrette	26.5	27.3

Clement et al. 1997

Acacia rigidula Bentham (these results need to be questioned)

Compound	Spring	Late Fall
(all via gc-ms)	ppm	ppm
2-Cyclohexylethylamine	0.8	35.2
N-2-Cyclohexylethyl-N-methylamine	1.2	47.1
Phenethylamine	872.3	1135.7
N-Methylphenethylamine	2314.6	5264.8
N,N-Dimethylphenethylamine	123.6	724.5
Amphetamine	6.7	11.8
Methamphetamine	nd	12.4
N,N-Dimethyl-α-methylphenethylamine	57.6	394.2
p-Hydroxyamphetamine	2.1	6.9
p-Methoxyamphetamine	nd	15.7
Tyramine	459.1	1699.2
N-Methyltyramine	237.4	1237.6
Hordenine	6.4	533.8
Dopamine	8.9	36.1
N-Methyldopamine	0.5	8.2
N,N-Dimethyldopamine	11.2	44.6
3-Methoxytryamine	1.8	12.9
N-Methyl-3-methoxytyramine	3.4	28.4
3-Hydroxy-4-methoxyphenethylamine	15.8	163.2
N-Methyl-3-hydroxy-4-methoxyphenethylamine	19.2	184.7
3,4-Dimethoxyphenethylamine	1.3	6.5
N-Methyl-3,4-dimethoxyphenethylamine	7.6	28.3
3,4,5-Trihydroxyphenethylamine	1.6	12.4
N-Methyl-3,4,5-trihydroxyphenethylamine	0.3	1.9
Mescaline	3.4	27.5
N-Methylmescaline	1.8	35.3
Trichocereine	0.2	13.8
3,5-Dimethoxytyramine	1.6	21.6
3,4-Dimethoxy-5-hydroxyphenethylamine	15.6	57.1
β-Methoxy-3,4-dihydroxy-5-methoxyphenethylamine	4.6	22.1
3,4-Dimethoxy-α-methyl-5-hydroxyphenethylamine	5.3	61.4
Nicotine	45.8	152.4
Nornicotine	23.4	84.3
Tryptamine	0.8	21.2
N-Methyltryptamine	4.6	54.9
N,N-Dimethyltryptamine	323.8	568.4
Anhalamine	9.6	48.7
Anhalidine (N-Methylanhalamine)	5.6	51.2
Anhalonidine	2.3	15.7
Peyophorine	3.8	43.4
Pipecolamide	872.8	978.2
p-Hydroxypipecolamide	241.6	353.1
1,4-Benzenediamine	104.8	129.6
4-Methyl-2-pyridinamine	341.5	567.3

Clement et al. 1998

This was the statement that had caught Sasha’s attention:
“[…] mass spectral library and the NBS mass spectral library of standards. Preliminary identification was made by library comparison, final identification was made by direct spectral comparison with the spectra of an authentic sample obtained from the GC-MS. Authentic samples were either purchased or prepared by known chemical procedures. “

In the INSIDER interview mentioned above, Dr. Clement affirmed synthesizing their samples due to distrusting reliance on published spectra alone.

What has always seemed peculiar to me about these two papers was not simply the wealth of never-before (or since) reported natural compounds or the appearance of so many known alkaloids that were novel to the Acacia species, but the authors’ apparent lack of interest in making further comment about any of their myriad of new discoveries or publishing any additional papers about those finds. Even if encountering only Nortriptyline, that alone would have generated a paper for most natural products chemists. The discovery of the previously known cactus alkaloids and a patented pharmaceutical in a common forage plant would both seem to merit at least some additional words in print. As Sasha similarly commented, “What caught my curiosity immediately was the casual indifference shown to what is certainly an extraordinary discovery.”

While it seems baffling for all of the authors to say so little about their new discoveries in those two papers, they also subsequently appeared to lose all interest in anything but the previously and routinely reported phenethylamines. I’m only aware of a couple of reiterations from Clement & Forbes where mescaline and/or amphetamines were even mentioned (both in 1998) and one oblique allusion to amphetamines was made in the form of a reference to potentially reduced MAOI activity in animals ingesting guajillo.
I can thusfar locate only one peer review publication appearing after 1998 that included one or the other as a contributing author which made any comment or reference at all about the ‘new’ alkaloids. That being Windels et al. 2003 which said of Clement et al. 1997: “More than 33 amines and alkaloids have been isolated from guajillo, with tyramine and NMP comprising 40-45% of total amine concentrations in spring and late fall” and made reference to the “many secondary plant chemicals” mentioned in that earlier account.
Among the other pertinent appearances of this information was its inclusion in a chapter contributed by Clement & Forbes to the 1998 Toxic Plants and Other Natural Toxicants edited by Tam Garland & A. Catherine Barr. In what is essentially an overview of the work published in 1997 and 1998 with additional commentary, an unexplained and largely overlooked modification is made to a comment made in the earlier account, “Smith (1977) does not report the presence of amphetamines in any plant family, and they are unlikely to be natural products.” [Bold emphasis added by me. See Endnote B on this page.] Compare that to the variant wording in Clement et al. 1998.

All that is totally clear is that the analytical accounts concerning Clement & coworker’s analysis of Acacia berlandieri and Acacia rigidula need more transparency and would benefit from a single accounting or overview that is lacking internal data conflicts or at least clarifies their origin and meaning. If they suspected that artifacts arising in gc-ms were involved it would be nice for that to be more widely understood as their research is still being cited as actually finding what was reported.

It is worth comparing the assorted details that have been published by the workers who have analyzed these two species of Acacia. A brief overview of the pertinent documents in that body of work is below (along with notes listing my known reference literature deficits). Those mentioning Acacia berlandieri are presented first, followed by Acacia rigidula. They are listed in the chronological order of their appearance. I am still missing some papers which have been noted and am additionally missing several papers that have not been noted. Whatever of that material actually merits inclusion here will be used to update this page after it comes to hand.

Published analytical accounts for Acacia berlandieri.

Camp 1956 was Bennie J. Camp’s dissertation at Texas A&M University in which he isolated what was believed to be the causative agent of limberleg, determined its structure through physical rather than spectral means, proving it through synthesis and the evaluation of the pharmacology and toxicity of the synthetic when compared to the natural compound.
Leaf material collected in the Del Rio area was determined to contain N-Methylphenethylamine at 0.54% by dry weight.

Camp & Lyman 1956 was the first peer-reviewed publication that reported the presence of N-Methylphenethylamine in Acacia berlandieri.

I have not yet obtained a copy of Camp & Lyman 1957.

Camp & Moore 1960 published a synthesis for N-Methylphenethylamine and a quantitative assay.
They also looked at potential seasonal fluctuations in the total amine content of Acacia berlandieri (using leaves collected during 1958):

May	0.66%
June	0.46%
July	0.42%
August	0.46%
September	0.28%
October	0.46%

Camp et al. 1964 reported N-Methyl-phenethylamine in Acacia berlandieri along with two additional alkaloids:
Tyramine & N-Methyl-tyramine.

Adam & Camp 1966 also isolated alkaloids from Acacia berlandieri.
These workers noted that sheep and goats may ingest this plant exclusively for 6-12 months before developing guajillo wobbles or limberleg. As long as it is not the exclusive food for prolonged periods involving drought, this is considered an important browsing material for both wild deer and domestic livestock. When the poisoning does occur, the fatalities rates are typically very high. See comment under Lupton below.
They reported:
N-Methyl-phenethylamine
Tyramine
N-Methyl-tyramine
Hordenine (trace) [A comment was made that hordenine could only be identified after being isolated and could not be detected when in combination with the other alkaloids, due to its low concentration.]

Enzman 1968 is a review summarizing the results of Adams & Camp 1966 and Camp & Lyman 1956; adding some previously published identification criteria for their reported alkaloids.

Evans et al. 1969 has been cited as a source investigating the seeds but did not evaluate this species. Acacia berlandieri was mentioned by Evans only briefly and in passing during the discussion of prior work reporting N-methyltyramine from Acacia species.

I have not yet obtained Forbes 1991.

Pemberton et al. 1993 was an account of an isolation approach for assaying Acacia berlandieri. Using plants collected in Zavala County, they reported Tyramine, N-Methylphenethylamine and what they believed to be N-methyltyramine. They were unable to confirm their identification of N-methyltyramine due to lacking a reference standard for comparison.

Forbes et al. 1995 studied alkaloid levels over a period of months and attempted to correlate the levels of Tyramine and N-Methylphenethylamine with factors such as date of harvest, age of growth and rainfall. They could not observe any meaningful differences to be closely correlated with rainfall or season of harvest but reported that there was a significant increase in the alkaloids levels of both alkaloids contained in young regrowth.

A pertinent non-analytic observation on guajillo toxicity:

Lupton et al. 1996 compared mohair production in two herds of goats; one in South Texas and one on the Edwards Plateau. Following dry years, when the alkaloid level in guajillo would be anticipated to peak, the South Texas population lost a significant number of animals; far more than did those on the Edwards Plateau. Both herds began with 100 animals. By the end of the five-year study only 45 goats were still alive in the South Texas group with 41 of the 55 deaths occurring between February 1988 and August 1989.

Clement et al. 1997:
The reported results are presented in a table above.
The use of an inert atmosphere (argon) is mentioned twice in this paper.
1) “Particular care was taken to maintain the extracts and isolated under an inert atmosphere. Left unprotected, the isolated amines and alkaloids readily absorbed atmospheric CO2 and decomposed with significant polymerization being detected detected.”
2) “A pilot study established that the extracts could be safely concd by rotary evapn (H2O aspirator). […] These organic extracts were combined, dried with MgSO4, filtered, concd under vacuum, and stored under argon prior to analysis by GC-MS.”
The reference standard source is given as:
“Authentic samples were either purchased or prepd by known chemical procedures.”
Their report of mescaline, mescaline derivatives and the previously known cactus isoquinolines was mentioned almost casually in passing. Curiously the presence of mescaline is never noted to be a novel observation outside of the Cactaceae or for the genus Acacia but there is one comment made concerning the amphetamines. “To our knowledge this is the first report of amphetamines in the genus Acacia. Smith (1o) in his review of the phenethylamines does not report the presence of amphetamines in any plant family. ” Compare that to a partially similar quote drawn from Clement & Forbes 1998. [See Note B]

Forbes & Clement 1998 overviews the same material from Clement et al. 1997 (combined with Clement et al. 1998).

Clement & Forbes 1998 does as well but, in one particular comment, leaves off a sentence and adds a few more words. “Smith (1977) does not report the presence of amphetamines in any plant family, and they are unlikely to be natural products.” The comment, like so much else in this story, is left unexplained.

Siegler et al. 1986 investigated polyphenolic and other tannins in terms of content and composition.

Windels et al. 2003 evaluated the amine concentration in regrowth resulting from a practice known as aeration in which the above ground parts of the plant are damaged with large nobby mechanical rollers. N-Methylphenethylamine increased in the leaves on regrowth following aeration and did so more on leaves from juveniles stems than on mature stems. Tyramine was not correlated with aeration but showed dynamic changes during the study period. There is one strange comment included considering that Forbes was a coauthor: “The relative costs and benefits to an animal of mechanically treating guajillo will not be clear until nitrogen in mature and regrowth guajillo is fully characterized and more is known about the toxicity of guajillo’s many secondary plant chemicals (Clement et al. 1997).”

There are two reasons that comment seems strange to me:
1) Much actually IS known about the pharmacology, toxicity and mechanisms of action for almost all of those compounds that Clement listed, the majority are very familiar and pharmacologically studied,
and
2) Apparently no work on that subject was ongoing during the six years in between those two papers (and none since that time) leading me to wonder what vehicle was envisioned as possibly adding more understanding. In what subsequent work was done overall the focus has been almost entirely on N-methylphenethylamine with a lesser amount of interest in tyramine. Unless I have missed one or more papers, none of the other of “guajillo’s many secondary plant chemicals (Clement et al. 1997)” saw any investigation or evaluation of their possible role in guajillo toxicity.

Published analytical accounts for Acacia rigidula:

There have been comparatively fewer looks at A. rigidula.

Camp & Norvell 1966 evaluated a number of additional Acacia species including Acacia rigidula.
They reported Acacia rigidula to contain 0.025% total alkaloid by dry weight and identified:
N-Methyl-phenethylamine
N-Methyl-tyramine

Evans et al. 1969. Acacia rigidula was mentioned by Evans only in passing in a sentence listing prior reports of N-methyltyramine from Acacia species.

Siegler et al. 1986 analyzed the content and composition of polyphenolic and other tannins in this species.

Clement et al. 1998:
Their reported results are presented in a table above.
As was also the case in 1997 is curious that their discoveries of amphetamines, mescaline and assorted cactus alkaloids are mentioned rather casually in this paper.
Comments appearing in this paper concerning degradation and the use of argon:
1) “Particular care was taken to maintain the extracts and isolates under an inert atmosphere. Left unprotected, the isolated amines and alkaloids readily decomposed.”
2) Clement describes extracting fresh material starting with it still frozen and extracting continually with methanol for 24 hrs in a soxhlet extrator. After removal of methanol it was extracted another 24 hours with chloroform. “A pilot study established that the extracts could be safely concentrated by rotary evaporation (water aspirator).” After concentration they dissolved the methanol residue in chloroform and extracted their alkaloids with HCl. After neutralization they extracted using chloroform followed by ethyl acetate. “These organic extracts were combined, dried with MgSO4, filtered, concentrated under vacuum, and stored under argon prior to analysis by GC-MS.”
There are two more instances when argon is mentioned in this paper. One was when performing an aqueous acidic etraction that was said to have been “stirred under argon at 60° overnight” with the additional comment “The organic extracts were combined, dried over MgSO4, filtered, concentrated under vacuum, and stored under argon prior to analysis by GC-MS.”
Comments made in this paper concerning their identifications and use of reference standards:
“Quantification of the levels of each compound was based upon standard curves generated with authentic samples.”
“Preliminary identification was made by library comparison, final identification was made by direct spectral comparison with the spectra of an authentic sample obtained from the GC-MS. Authentic samples were either purchased or prepared by known chemical procedures.”
One other comment is worth noting as it is one of the only bits about the novelties in this paper that are referred to in later works:
“However the presence of the amphetamines suggests the possibility for a reduction of monoamine oxidase activity.”

Forbes & Clement 1998 overviews the same material as in Clement et al. (1997 &) 1998.

Clement & Forbes 1998 also overviews Clement et al. 1997 & 1998 but adds a small bit of discussion expressing doubt about some pertinent parts of their results.

I have not yet obtained Pawar et al. 2010.

Pawar et al. 2014 analyzed dried samples of Acacia rigidula leaves, twigs and bark, as well as assorted dietary supplements that were said to contain it.

Pawar’s samples:
Val Verde County – collection November 2009 (by M. Eason)
Tyramine, Tryptamine and Phenethylamine.
Starr County – collection February 2012 (by M. Eason)
Tyramine, Tryptamine, Phenethylamine, traces of N-Methylphenethylamine.
Maverick County – collection February 2012 (by M. Eason)
Tyramine, Tryptamine, Phenethylamine, traces of N-Methylphenethylamine and traces of N-Methyl-tyramine.
Hidalgo County – collection September 2009 (purchased dried)
Tyramine, Tryptamine and Phenethylamine.

Pawar reported the positive detection of N-Me-PEA (below their threshold for quantification) in two samples and found no evidence for it in the other two samples.

During her 2013 interview with INSIDER, Dr. Clement made the following comments about the use of argon during their investigations.
“Clement explained the leaves were extracted using a soxhlet extraction system employing methanol as the extraction solvent. “Because of prior experience with the guajillo extractions, the soxhlet was purged with argon to minimize exposure to ‘air.’ Following extraction, the extract was concentrated on a rotary evaporator (vacuum released to argon again to minimize exposure to ‘air’). The residue was dissolved in dichloromethane and extracted with 10-percent HCl—it was not as critical at this point to keep the acidic extract under argon to prevent side reactions. The HCl extracts were combined, neutralized with NaOH and extracted with dichloromethane (argon blanket again necessary). We had tested the extraction and neutralization procedure with tyramine to make certain that the conditions allowed recovery of this phenolic amine and related material.” She further noted the extracts were combined, concentrated and kept under argon in the freezer until analysis with GC/MS (gas chromatography/mass spectrometry.)”
In their actual papers in 1997 and 1998, only the use of chloroform was described. Dichloromethane (CH2Cl2) was not mentioned in either account.

Pure alkaloids evaluated for contributions to reproductive harm:

Completion of this entry will be forthcoming, but has been delayed pending requisite additional literature access.
T.D.A. Forbes was a contributing author on all seven papers below.
Carpenter et al. 1992 & 1994
Forbes et al. 1991, 1993 & 1994
Vera-Avila et al. 1996 & 1997

Pharmacological activity of N-methyl-β-phenethylamine:

Camp 1970 (I do not yet have)
Stohs & Hartman 2014 (a review of the published literature — available online as a free PDF: onlinelibrary.wiley.com/doi/10.1002/ptr.5231/pdf)

Conclusions:

While we cannot know what exactly occurred in Dr. Clement’s lab it is clear that her published results claiming the presence of amphetamines in these Acacia species is not valid. This should be considered to be true for the other novelties in both papers including the wealth of cactus alkaloids.
All of those require confirmation through replication by someone and it is doubtful that can be accomplished.

Published references used or wanted:

Papers that I have not yet obtained are noted and came from the FDA toxic plant database or were cited by Camp or Forbes.

Adams, Herman R. & Bennie J. Camp (1966) Toxicon, 4: 85–90. “The Isolation and Identification of Three Alkaloids from Acacia berlandieri.”

Camp, Bennie J. (1956) PhD dissertation, Texas A&M University, “The alkaloid of Acacia berlandieri, N-Methyl-β-phenylethylamine.”

Camp, Bennie J. (1970) American Journal of Veterinary Research, 31 (4): 755–762, “Action of N-methyltyramine and N-methyl-beta-phenylethylamine on certain biological systems.” [Have not yet obtained a copy.]

Camp, Bennie J. & Carl M. Lyman (1956) Journal of the American Pharmaceutical Association, Scientific Edition, 45 (11): 719–721. “The Isolation of N-Methyl beta-Phenethylamine from Acacia berlandieri.”

Camp, Bennie J. & Carl M. Lyman (1957) The Southwestern Veterinarian, 10: 133–134. “The toxic agent isolated from Acacia berlandieri, N-methyl beta-phenylethylamine. ” [Have not yet obtained a copy.]

Camp, Bennie J. & Joan A. Moore (1960) Journal of the American Pharmaceutical Association, Scientific Edition, 49 (3): 158–160. “A Quantitative Method for the Alkaloid of Acacia berlandieri.”

Camp, Bennie J. & Michael J. Norvell (1966) Economic Botany, 20 (3): 274–278. “The Phenylethylamine Alkaloids of Native Range Plants.”

Camp et al. (1964) Annals of the New York Academy of Sciences, 111 (2): 744–750. “The Chemistry of the Toxic Constituents of Acacia berlandieri.” (Bennie J. Camp, Ray Adams & J.W. Dollahite)

Carpenter, B.B. et al. (1993) Journal of Animal Science, 71 (Suppl. 1): 208. “Sympathomimetic compounds present in Acacia berlandieri alter ACTH, cortisol, norepinephrine and GnRH-induced LH release in wethers.” (B.B. Carpenter, T.D.A. Forbes, D.R. Tolleson & R.D. Randel) [Have not yet obtained a copy.]

Clement, Beverly A & T. David A. Forbes (1998) Toxic amines and alkaloids from Texas acacias, pages 351–355, (Chapter 69) in Toxic Plants and Other Natural Toxicants edited by Tam Garland & A. Catherine Barr.

Clement, B.A. et al. (1997) Phytochemistry, 46 (2): 249–254. “Toxic Amines and Alkaloids From Acacia berlandieri.” (Beverly A. Clement, Christina M. Goff & David A. Forbes)

Clement, B.A. et al. (1998) Phytochemistry, 49 (5): 1377–1380. “Toxic Amines and Alkaloids From Acacia rigidula.” (Beverly A. Clement, Christina M. Goff & T. David A. Forbes)

Enzman, F. (1968) Fresenius Journal of Analytical Chemistry, 237 (6): 440–441, “Über die Isolierung und Identifizierung von drei weiteren Alkaloiden aus Acacia berlandieri (Guagillo).”

Evans, C.S. et al. (1979) Phytochemistry, 18: 2022–2023. “N-methyltyramine, a biologically active amine in Acacia seeds.” (Christine S. Evans, E. Arthur Bell & E. Stewart Johnson) [This paper only mentions our two species.]

Forbes, T.D.A. et al. (1991) PR (Texas Agricultural Experiment Station) Oct 1991. (4875) pp. 22–25, “Seasonal production of phenolic amines by Acacia berlandieri.” (T.D.A. Forbes, I.J. Pemberton, G.R. Smith, C.M. Hensarling & D.R. Tolleson) [Have not yet obtained a copy.] (Note: D.G. Tolleson, appearing in reference listings, is incorrect.)

Forbes, T.D.A. et al. (1993) South African Journal of Animal Science, 23: 196–200. “Effects of exogenous amines on reproduction in female angora goats.” (T.D.A. Forbes, D.R. Tolleson, C.M. Hensarling & R.D. Randel) [Have not yet obtained a copy.]

Forbes, T.D.A. et al. (1994) Journal of Animal Science, 72: 464–469. “Effects of N-methyl-(beta)-phenethylamine on GnRH stimulated luteinizing hormone release and plasma catecholamine concentrations in wethers.” (T.D.A. Forbes, B.B. Carpenter, D.R. Tolleson & R.D. Randel)

Forbes, T.D.A. et al (1995) Journal of arid environments, 30 (4): 403–415, “Seasonal variation of two phenolic amines in Acacia berlandieri.” (T.D.A. Forbes, I.J. Pemberton, G.R. Smith & C.M. Hensarling)

Forbes, T.D.A. & B.A. Clement (1998) Bottom Line, Texas A&M University, Uvalde, BL-R8, “Chemistry of Acacia‘s from South Texas.” (Essentially a short summary of Clement et al. 1997 & 1998.)

Pawar, R.S. et al. (2010) Planta Medica, 76 (5): P54, “Phytochemical Investigation of Acacia rigidula Leaf.” (R.S. Pawar, E. Grundel, E. Mazzola, M. Eason, A.J. Krynitsky & J.I. Rader) [Have not yet obtained a copy.]

Pemberton, I.J. et al. (1993) Journal of Animal Science, 71 (2): 467–470, “Technical note: an improved method for extraction and quantification of toxic phenethylamines from Acacia berlandieri.” (I.J. Pemberton, G.R. Smith, T.D.A. Forbes & C.M. Hensarling)

Price, D.A. & W.T. Hardy (1953). Journal of the American Veterinary Medical Association, 122: 223–225. “Guajillo poisoning of sheep.” [Have not yet obtained a copy.]

Shulgin, Alexander T. “Sasha” (2001) Dear Dr. Shulgin, Center for Cognitive Liberty & Ethics, [http://www.cognitiveliberty.org/shulgin/adsarchive/acacia.htm]

Siegler, D.S. et al. (1986) Economic Botany, 40: 220–232. “Tannins from four common Acacia species of Texas and northeastern Mexico.” (D.S. Siegler, S. Seilheimer, J. Keesy & H.F. Huang)

Stohs, Sidney J. & Michael J. Hartman (2014) Phytotherapy Research, “A Review of the Receptor Binding and Pharmacological Effects of N-methyltyramine.” Published online by Wiley; Epub 2014 Oct 2, with no page numbers. [onlinelibrary.wiley.com/doi/10.1002/ptr.5231/pdf]

Vera-Avila, H.R. et al. (1996) Domestic Animal Endocrinology, 13: 285–296. “Plant phenolic amines: potential effects on sympathoadrenal meduallary, hypothalimic-pituitary adrenal, and hypothalamic-pituitary-gonadal function in ruminants.” (H.R. Vera-Avila, T.D.A. Forbes & R.D. Randel)

Vera-Avila, H.R. et al. (1997) Journal of Animal Science, 75: 1612–1620. “Effect of dietary phenolic amines on testicular function and luteneizing hormone secrection in male Angora goats.” (H.R. Vera-Avila, T.D.A. Forbes, J.G. Berardinelli & R.D. Randel)

Windels, S.K. (1999) M. S. Thesis, Texas A&M University- Kingsville. “Effects of roller-chopping on white-tailed deer nutritional carrying capacity and habitat, and phenolic amine content of guajillo in northeastern Mexico.”

Windels, S.K. et al. (2003) Journal of Range Management, 56: 529–533. “Effects of aeration on phenolic amine content of guajillo.” (Steve K. Windels, David G. Hewitt & T. David A. Forbes)

Endnotes

Endnote A: To suggest the level of interest the accounts from Clement & coworkers generated, what follows are results from a Google search on 11 January 2015. The listed words below are the terms used for the search followed by the number of hits that resulted. (Many of the following phrases were suggested by Google as another one was being typed.)
The number is the estimated total given on the results page. No effort was made to gauge a percentage for duplicate entries, meaningless hits or bad links.
Nortriptyline found in acacia 1,050,000
methamphetamine found in acacia 874,000
mescaline found in acacia 309,000
mescaline acacia tree 178,000
amphetamine in acacia 122,000
methamphetamine acacia tree 22,000
acacia berlandieri methamphetamine 4,690
acacia berlandieri mescaline 4,740
acacia berlandieri DMT 5,070
acacia berlandieri DMT extraction 2,040 (Google suggested this as I was typing DMT.)
acacia rigidula methamphetamine 6,690
acacia rigidula mescaline 3,680
acacia rigidula DMT 4,770
acacia methamphetamine 48,500
acacia mescaline 35,500

Endnote B: Smith 1977 was largely a simple tabular listing of the phenethylamines reported to occur in plants. While a question might be raised as to why the lack of an entry on Smith’s list would indicate that amphetamines did not occur in plants (absence of evidence is not proof of absence), Smith actually did include the half dozen naturally occurring amphetamines that were known in 1977.
In particular Smith listed norephedrine, cathine, ephedrine, pseudoephedrine, methylephedrine, & methylpseudoephedrine as variously occurring among 32 plant species. Those included Aconitum napellus, Catha edulis, 25 species of Ephedra, Halostachys caspica, Roemeria refracta, Sida sp, Sida cordifolia, and Taxus baccata.
Ephedrine has also been reported to occur in small amounts in the rhizomes of some Pinellia ternuata, (Oshio et al. 1978).
Those two references:
H. Oshio et al. (1978) Chemical and Pharmaceutical Bulletin, 26: 2096–2097, “Isolation of l-ephedrine from pinellia tuber.”
T. A. Smith (1977) Phytochemistry, 16: 9–18, “Phenethylamine and related compounds in plants.”

cocorra

Posted on December 12, 2014 by admin

Amanita calytroderma is more often known as cocorra.

I’m not saying to eat this one. It’s not a bad mushroom. Some people think it is great. It’s not my favorite as they are a bit crunchy but they do have a profoundly rich flavor. Wow. In a hearty soup stock this contribution of this fungus is insane. I’ve heard they make great pickles but just try to get someone else to eat one.

The toxic look-alike problem is really worth getting educated on as it is more likely to kill a person not-nearly-quickly-enough rather than just making them sick. I’ve *heard* that the toxic Amanitas taste really great too. Or at least that is what has been claimed by survivors; one of which also related entering a demonic realm of vividly-intense hallucinatory hell that was unlike anything I’ve heard described before or since.

Both edible and deadly Amanitas can sometimes be found growing together so consumption of the unexpanded “eggs” is not a smart idea.

These are correctly identified. Please do not use them for identification!

Amanita calyptroderma

Amanita calyptroderma

Amanita calyptroderma

Amanita calyptroderma

Amanita calyptroderma

Amanita calyptroderma

Amanita calyptroderma

Amanita calyptroderma

matsutake

Posted on December 12, 2014 by admin

The white matsutake are making this a really fun and exciting time of year! Check out this next image. Maybe you find that exciting or maybe you don’t?

Tricholoma magnivelare

Did you spot my quarry?

I’ll get a little closer. That one is actually easier than most of them.

Tricholoma magnivelare

How about now? Its right there in the middle of things — peeking out.
Let’s move some of those leaves.

Tricholoma magnivelare

How about now? Clearly that is what I am after even if it shows just a bit of white.

It’s definitely a matsi. Let’s uncover it.

Tricholoma magnivelare

Aw! I got here too late. The veil has already broken.

Tricholoma magnivelare

It is a beautiful looking mushroom but not even close to being a number one. I should have found it a day or two ago (when I was at this same spot).

There’s another one. How did I miss that! I must have partially uncovered it with my foot just now.

Tricholoma magnivelare

That looks better.

Tricholoma magnivelare

Not as big but at least it’s a number one.

a number one Tricholoma magnivelare

It was a good year for white matsutake here in Mendocino County even if abundance meant they were not worth picking to sell. I heard buyers in Oregon were giving $4 a pound and that retail prices in Japan had dropped to something like $400US a kg. Risking my neck on sketchy slopes with duffy and loose-gravel footing for what might this year be averaging $12-16 an hour sure is a crazy thought. I’d rather do it for fun, take it slow, and enjoy some great meals. Besides they freeze great once cooked.

This was the first find of this year. I was too excited to leave all of the leaves intact before taking a photo. That is a typical habitat for them around here, heavy duff under tan-oak and huckleberries.

Tricholoma magnivelare

Tricholoma magnivelare

Some nice number ones. Some are tiny but they don’t reattach and grow so all were cooked.

Tricholoma magnivelare

I hope that your mushroom hunting this season goes as well or better!

Lophophora williamsii description

Posted on December 10, 2014 by admin

Description and characteristics of Lophophora williamsii

Plants are typically low growing, often almost flush with the ground. (Sometimes occurring as low mounds.) Rains and resulting water flow can rearrange the top surface of the soil leaving peyote plants with up to several cm of exposed stem or they can become completely buried by several cm. They are specialized at growing on sloping terrain.

East of Rio Grande City in Starr County

Presidio County

Lophophora-williamsii-habitat-Wirikuta-Hjeran-6

In habitat at Wirikuta.
Photo by Hjeran

During times of drought, and in preparation for winter, peyote can pull itself into the ground. New growth will occur as soon as favorable conditions return.

A welcomed rain following drought in Presidio County

Peyote has a deep taproot that is napiform (fat carrot or ice-cream cone shaped in general outline), tapering slowly from the above ground portion’s diameter, and weakly branching mainly at the distal end. It can be seen in instances such as Henning’s Anhalonium williamsii illustration that roots can sprout from almost anywhere on a cut peyote plant after it has been replanted.

Lophophora williamsii roots
Cactus Conservation Institute image

Especially towards the top there are greyish or brown coarse barky rings, formed by the shriveling of the outermost row of areoles that are becoming the top part of the nonchlorophyllaceous stem.

Lophophora williamsii root bark in Jim Hogg County

The roots are usually 8-11 cm long (4.) 3-5 inches long (5.)

Crown broken by passing traffic showing a cross section of the stem, the vascular bundle and the barky outer layer

Only with substantial age will the roots on rooted cuttings get tap-root like. Cuttings can never reform the single fat root peyote is noted for but each of their pups can go on to form their own tap roots, especially after their mother was decapitated. In this latter case the rootstock of the mother may eventually be sucked dry of life as the pups go on to become independent plants.
The roots that form are often whitish to tan, fleshy and weakly branching.

Lophophora-williamsii-deadcrown-pups-roots

pups forming separate roots following crown death (due to rot) of the mother Cactus Conservation Institute image

Roots that form tend to branch primarily at their base and only sporadically and weakly as this partially uncovered young plant illustrates. Notice how similar the branching of this seedling is to the branching of the solitary herbarium specimen that was shown earlier.

Young plant with the underground stem and roots largely exposed

Grows as, often dwarf, solitary heads. Occasionally budding at the base to form pairs or clusters. Budding occurs rarely in young plants and is more frequent in older plants. Many plants remain single, even if large. Small intact plants of double heads are sometimes encountered. One that initially looked cristate within several years had divided into two perfect heads.
Many times plants can be found joined underground. This is especially noticeable on plants which have pupped due to flush cut harvesting. As the wound heals, the cactus shrinks into its root and the pups form from an old areole on the subterranean stem, this most often occurs underground.
It must be mentioned that some people cut the plants below ground level and apparently obtain clumps as a result. It is clear the mortality goes up but how much has seen very few studies. The lower the cut the less stored tissues remain. If the cut is above the subterreanean stem there is almost a certainty of regrowth. If it occurs below that transition and leaves just root tissue there is no chance of regrowth as the requisite areoles were removed. If the cut falls someplace within the nonchlorophyllaceous stem itself there is still a chance for regrowth but the mortality goes up as the stored food reserves goes down adding an increased susceptibility to extremes of drought and weather. (See the studies of Terry & Mauseth 2006 for details on morphology and Terry et al. 2011, 2012 & 2014 for details on post harvesting regrowth and mortality.) One factor interfering with an adequate perception of loss by harvesters is that when deep cutting kills a plant the carcass often decomposes under the earth leaving no trace.

Lophophora-williamsii-areole-newgrowth-JimHoggCo

Harvested Lophophora williamsii with a new pup emerging at base

The base of pups not induced from injury only occasionally send out, mainly weak, roots of their own. Often in previously harvested rooted heads, there is no independent formation of roots by the resulting pups and they rely on the vascular system of the mother. Unless forcibly divided [Note 18] the pups remain connected as a part of the parent. In cases where the mother plant has been compromised or dies the pups can and do go on to form new tap roots.

Lophophora-williamsii-pups-independent-roots

Pups forming independent taproots following the crown death of the mother plant

In clumps, there is often one plant far larger than the rest unless clumping was induced by injury. New plants forming from injury, especially partial decapitation, are usually produced from the healthy and intact areoles peripheral to the injury, and, if multiple, will normally be of the same size. All variations of growth can normally be found in a large population of old plants.

Pupping is enhanced greatly by injury, especially if to the terminal portion of the head (apical meristem).

Lophophora-williamsii-JimHoggCounty-regrowth-postharvest

Regrowth after removal of the original crown

Occasionally peyote forms large mounds with great age. Mounds over a meter in diameter have been reported by many different reliable sources. Weniger says “often clustering to form up to 50 [heads] in one variety.”
These mounds are rarely encountered in Texas anymore. It was not always this way.

Jim Hogg County

The heads are rounded and usually more or less flattened on top. The center of the top is depressed and filled with woolly hair. They may be globose or somewhat cylindrical but all have depressed centers except when severely etiolated [Note 19] (6.).

Peyote infrequently forms crests [Note 20] but these are not infrequent in major cactus and succulent collections as they are highly sought after by cactus collectors. It is probable that crests can occur in any of the wild populations and in any Lophophora species. Occasionally, they are offered for sale as horticultural specimens that can sometimes exceed a foot in diameter. Belgian seed suppliers have offered seeds from cristate plants but it is doubtful crests would develop on the offspring. They showed no germination, in contrast to the ready germination of their other “species” and varieties.

More images can be found at sacredcacti.com

Pictures of a crested specimen can be found on Page 2904, fig. 2732 of Backeberg 1961 and on page 178 (# 738) in Hirao 1979 and also on page 1298 of Lamb & Lamb 1978 and on the back cover and pages 44 & 45 (as in-habitat color photos) in Grym 1997 and also in the black & white plate facing page 177 of Martin et al 1971.
A very useful search phrase for amazing images is “烏羽玉綴化“.

Lamb & Lamb commented that peyote crests grow quite well on their own roots so that grafting is not necessary (unlike many crests which are slow growing and rot prone.) Grafting of peyote crests is a common practice though as it is how most crests are multiplied for commercial propagation.

Lophophora williamsii echinata from Val Verde County with a crest starting

Lophophora williamsii echinata from Val Verde County starting to develop a crest. Cactus Conservation Image

Plants are firm and very succulent. Said by Lamb & Lamb 1974 and Weniger 1984 to be soft but I have found them only to be soft when in poor health or wet such as after heavy or prolonged rains, especially if during cool weather. Normally they are turgid and firm as a green tomatillo, but with an almost velvety feel. The friendly ‘touchability’ of this plant may be a part of its allure for many otherwise mainstream cactus growers.

Jim Hogg County

Val Verde County

Lophophora-williamsii-echinata-ValVerde-2011-4043

Val Verde County

The flesh of peyote, like many other cacti, typically has a gritty or sandy texture due to the presence of oxalate crystals as can be observed exposed by a predator in the image below. (In some cacti such as Echinocactus horizonthalonius oxalate can comprise 60% of the dry weight of the entire plant!)

Lophophora-williamsii-eaten-showing-interior

Lophophora williamsii in Jim Hogg County showing oxalate crystals inside of its flesh.

Peyote may be blue-green, greyish-green, bright glaucous green (usually only seen in bloated overfed cultivated plants), chalky blue and occasionally appearing reddish-green. All usually have a pronounced grey glaucescence or haze on their surface unless it has been abraded off by rough handling. This haze on their surface is due to a layer of small flakes of waxy material. Brown areas can develop during droughts and reddening or even purple coloration can be induced by cold and freeze stress.

Lophophora-williamsii-echinata-boquillas-4046

Boquillas, Mexico (in cultivation)

Val Verde County

Val Verde County

Anderson notes that a brown corky layer of unknown origin sometimes develops on cultivated specimens. This was encountered this once in a wild population in southwestern Zapata County. It doesn’t seem to hurt the plants but when present, sometimes spreads and becomes unsightly. I’m at least assuming this is what Anderson refers to:

Val Verde County (cultivated wild plant)

There are no leaves except microscopically during early development. (2.)

Literature gives sizes usually falling in the 4-12 cm. in diameter and 2-8 cm. tall range.

Weniger says Lophophora williamsii var. williamsii reaches 3 inches and var. echinata reaches 5 inches (5.)

In previous editions of Sacred Cacti I mentioned seeing larger – huge – many-ribbed Lophophora williamsii in the late 1970s. I now believe this was in error and that ALL of those plants were actually Lophophora fricii. I now believe that I was being lied to by the collector concerning their point of wild-collected origin.

Plants over 4 inches have always been of rare observance. Weniger comments that “var. echinata” can reach five inches in the longest dimension of its crown. Bohata et al. 2005 also pointed out the existence of some interesting larger Lophophoras in Mexico. They appear to need some study.
Normally Peyote reaches somewhere towards 3 or 4 inches and then fluctuates in size seasonally, occasionally by as much as an inch in all directions, for the rest of its life. It will continue to grow larger only in the sense that the root will continue growing into the earth, the crown will continue to replace most of what tissue is lost due to local environmental extremes and predatory challenges, and, in many cases, pups will be produced by the original stem.
Notice the extremely long roots in this next image (modified from Bravo 1937). It must have taken a long time the plant on the right to go from being a seedling to having its roots that deep in the earth. Hopefully the viewer noticed how the diameter of the plant itself did NOT steadily continue to grow larger during that process.

In the neighborhood of 8 ribs is what is most often thought of with peyote but the number is highly variable in any population. Anderson 1980 says 4-14 ribs. If a peyote has more ribs than 14 it should be suspected to be Lophophora fricii.

Jim Hogg County, Texas

Boquillas, Mexico (cultivated)

5 ribbed plants are rare past somewhere around one inch in size. Only occasionally do they not soon go on to form more ribs. While some authors have stated that it is simply a juvenile form of the plant, 5 ribbed plants do occasionally reach at least 3 inches in diameter and other 5-ribbed plants will sometimes stay tiny even with age.

seedlings from Starr County seeds (Cactus Conservation Image)

More images can be found at sacredcacti.com

The ribs are defined by furrows which are easily divided in a cut plant, and may be straight or in spirals. Sometimes the ribs are irregular or even indistinct. Usually they are broad and rounded and have shallow transverse furrows, forming tubercles or podaria. Schultes & Hofmann 1980 refer to them as “more or less regular, polyhedral…” and Benson 1982 calls them “irregularly hexagonal”. They may bulge outward but especially in older tubercles they tend to flatten out and become low, broad and rounded. They can reach an inch in “diameter”.

Lophophora-williamsii-echinata-Brewster-8986

Brewster County

The ribs and tubercles or podaria are highly variable in appearance from individual to individual, as well as seasonally. Part of the reason for this is that the ribs serve an important function for cacti as they enable the body to swell or contract in response to the available water.

Lophophora-williamsii-WestTexas-dehydrated-ribbing-2009

Drought-stressed in Presidio County

Rain-soaked in Jim Hogg County

The highly variable nature of peyote’s appearance underlies the problems it gave some botanists in Europe who had never seen an actual population first-hand (it has also caused many problems even for those who had field experience).

Many more images can be found at sacredcacti.com

Areoles are usually arranged linearly along ribs or at the apices of the hump-like tubercles or podaria. They are set from 1/2 inch to 1 inch (1.3-2.5 cm) Lamb & Lamb, 0.9-1.5 cm Anderson, 12-25 mm Benson, apart. The areoles are flat and round. They range from 2 to 4 mm in diameter.

The areoles in peyote only bear flowers when young.

Lophophora-williamsii-JimHogg-spines_seedling

wild seedling in Jim Hogg County

During the first year of growth each areole bears a dense tuft of white and more or less silky hairs to 7-10 mm long. (2.)

Val Verde County

Chihuahua, Mexico (under cultivation)

Later, each mature areole bears a dense, cylindroid tuft of soft trichomes (woolly hairs), 8-15 mm apart, 1-5 mm in diameter. (1.)

Val Verde County (under cultivation)

The persistent tufts of hairs are usually equally spaced on the ribs. (4.). They usually feel silky and may stand erect and matted or have the ends bent or broken off entirely.

Wool is yellowish or whitish, usually turning grey with age and it is sometimes broken or worn off.

Lophophora-williamsii-seedlings-Anonymous

Lophophora williamsii seedlings.
Photo by Anonymous

Spines are usually absent except in very young seedlings which bear a few weak bristle-like, usually white, sometimes yellowish, spines on their crown.

seedling of Lophophora williamsii echinata

While this is what is easily observed, Mauseth 1983b points out that peyote does in fact “…have spines, but they are so short that they do not even reach the top of the depression in which the areole is located.” However, occasionally tiny spines can show up noticeably on wild L. williamsii.

More images can be found at sacredcacti.com

A known exception to this concerns those plants referred to as L. jourdaniana which normally show some longer & quite noticeable spines, especially on young areoles.

Lophophora jourdaniana

Jim Hogg County

Both flowers and fruits form on young areoles, near apex of stem, [borne at umbilicate centre of crown, (4.)], each at apex of a low new tubercle in a felted area adjoining the spine-bearing part of areole and partially merging with it. A circular scar persists at the site after the fruit has fallen. (2.)

Flowers are normally solitary but occasionally there will be several flowers either rapidly following each other or blooming together. 5 is the most I have ever witnessed first-hand. They couldn’t open fully because they were so close together. See photo of 3 in McLaughlin 1973 and in Schneck. See Mount 1993 for a picture with 5 blossoms open at one time.

Flowers are 1 cm to 2.5 cm in diameter, and 1-2.4 cm long (3 cm long. 2.). The floral tube has been described as “rotate-campanulate”(4.), “funnelform”(2.), and “bell shaped”(5.). Each flower is surrounded by a mass of long hairs.

Val Verde

Flower size, color and petal shape can be variable even within single populations. Pinkish, whitish blushed pale pink or rose (5.) are the most common flower colors. Dirty white, pure white, or pale yellow yellow are very rarely encountered.

More images can be found at sacredcacti.com

Populations observed in Texas usually were light pinkish with a darker pink, occasionally greenish, mid-stripe on each petal or whitish with a pink mid-stripe. More rarely they were whitish sometimes having a faint greenish mid-stripe on each petal that is most colored on the outside.

More images can be found at sacredcacti.com

grown from Starr County seeds (JAV)

The flowers in Weniger’s echinata have so far have had light pink petals with a darker pink midstripe. (6.) They have tended to be a bit more oval rather than round.

More images can be found at sacredcacti.com

Outer perianth segments and scales ventrally greenish, callous tipped (4.) Outermost perianth segments greenish with entire edges (5.)

Sepaloids with greenish middles & pink margins, largest narrowly oblanceolate, 9-15 mm long, to 3 mm broad, acute and strongly cuspidate, the margin entire. (2.)

Jim Hogg County

Outer perianth segments have greenish midribs and greenish-pink or whitish margins, the largest ones elliptical, 3-12 mm. long, 1-3 mm broad, mucronate, marginally minutely ciliate distally (1.)

[Outer perianth segments = sepaloids = sepals]

Presidio County (Chinati) under cultivation

Inner perianth segments pink, pinkish-red, or white, often with a darker midstripe, the largest ones are typically elliptical, 8-22 mm long, 2-4 mm broad, mucronate or occasionally attenuate, margins ciliate or entire. (1.)

Inner segment almost linear, pale pink to rose, white or yellowish. (5.)

Lophophora-williamsii-flower-WestTexas-petalclose

Presidio County

Petaloids often pink in their middles, pale to nearly white at margins, largest oblanceolate, 12-15 mm long, to 4 mm broad, acute and cuspidate, entire; filaments pale, more or less 2 mm long. (2.)

[Inner perianth segments = petaloids = petals]

Flowering will usually begin around 5-6 years of age (or when they reach around 1 inch in diameter) from seed. It can begin much sooner if they are grafted; often within a year after making the graft even if starting with a young seedling.

Lophophora-williamsii-echinata-flower-close

Presidio County

The style is white, tinged with pink, reddish or rarely magenta, to 9 mm (2.) [5-14 mm (1.)] long, more or less 1-1.5 mm at greatest diameter;

The (3-)5-7 lobed stigmas are naked, linear, thin and flattened; 2 mm long, 1+ mm broad, and can be reddish, pink or yellowish;

Ovary is small, naked and surrounded by hairs (to 12 mm long). “Ovary in anthesis [is] turbinate”, 3-4.5 mm. long, smooth, not scaly. (2.)

Filaments are whitish, or rarely magenta (1.) and shorter than perianth segments (4.).

Presidio County

They bear 3-7 yellow anthers, 1-1.4 mm long.

Jim Hogg County

Lophophora-williamsii-echinata-ValVerdeCo-9631

Val Verde County

The stamens of L. williamsii are thigmatropic so respond to touch by curling. A toothpick was used to gently touch the anthers in the photo below.

More images can be found at sacredcacti.com

The pollen in L. williamsii is highly variable in size, shape and aperture. The grains are more or less spheroidal (around 12 different geometric shapes), 0-18 colpate, and is (14.9-) 26-63.4 mm in diameter (averaging 40 microns) (1.) [Image]

[See also Anderson & Stone 1969]

Normally flowering from March through September (1.)

There are usually two peaks of flowering, one in spring and one in summer, generally these are following rain.

Cultivated plants have been observed to flower both earlier and later and can seemingly occur any month of the year if the conditions are right (6.)

Pizzetti 1985: entry #154. Has picture of a plant with a flower and pups.

Innes & Glass 1991 Also features a nice color picture in flower; on p. 150.

Color pictures can also be found in Grym 1997.

Fruits are small, slim, elongate, nude and clavate (club-shaped), or nearly cylindroid and enlarged gradually upward, (12-)15-20 mm (1, 2.) (3/8-3/4 inch) (5.) long, more or less (2-)3-5 mm diameter (1, 2.) The umbilicus is large or the perianth parts persistent, and the fruit emerges rapidly from within the trichome at maturity.(1.)

They are red to pale pinkish when ripe. Fleshy and indehiscent at first, they become dry and brownish-white, or eventually blackish, at full maturity. Seeds are released by the pods drying and breaking.

ripe & dying

Ripe & dry

full of ripe seeds

The fruit walls are thin, transparent when fresh, and bare, without tubercles, scales, spines, hairs or glochids, although a few small hairs can rarely persist on the end of the fruit.

Fruits mature 9-12 months after fertilization. (1.) It is common to find fruit emerging around the same time as the flowering periods. Gerhard Koehres (who has extensive experience with commercial seed production using grafted seedlings) has commented that fruit can form from the early flowers within around 8 weeks but has also found that the fruit for the later blossoms often do not emerge until the following year. Clearly this subject is apparently not as cut and dried as was presented by Anderson and merits some study.

Seeds are usually are spread by water and possibly sometimes with the help of ants. It is almost certain that ants harvested the seeds from this Lophophora fruit in Presidio County.

Lophophora-williamsii-echinata-PresidioCo-fruit-2010-6659

Characteristic hole made by ants

Whether they are what is responsible for the placement of these two plants with their crowns at an almost vertical orientation is a matter of fascinating speculation.

Presidio COunty

Seeds are black, tuberculate-roughened (4.), (verrucose) pyriform (1.), densely papillate (2.), longer than broad, 1-1.5 mm. (2.) [“about 1/16 in.” (5.)] long, 1(+) mm broad, 0.8 mm thick; with broad whitish basal hilum (large, flattened, depressed and sometimes v-shaped), enlarged upward from the hilum, resembling those of Cereus (2.), Ariocarpus and Obregonia (1). [Image]

Lophophora-williamsii-echinata-loose-seeds-2531

Check out all those seeds. You can actually see the shape of the hilums clearly in the larger viewing sizes!

They set seed readily even in cultivated plants. It is not uncommon to find seedlings growing in with older specimens.

Lophophora-williamsii-echinata-boquillas-4041

Spontaneous seedlings (Boquillas, Mexico)
(under cultivation)

Cotyledons coalescent (1.), accumbant, not foliaceous. (2.)

Chromosome number 2n=22

The closest living relative to Lophophora williamsii, based on the molecular cladistics of Rob Wallace, is Obregonia denegrii.

Obregonia denegrii

Description adapted from (1-5 include pictures.)

1. Anderson 1980: pp. 179-181.

2. Benson 1982: pp. 680-683.

3. Lamb & Lamb 1974: pg. 196.

4. Schultes & Hofmann 1980: pp. 221-222.

5. Weniger 1984: pp. 138 -140.

6. Personal observation.

Useful search terms for locating additional imagery:

烏羽玉 & 乌羽玉（Lophophora williamsii）

子吹乌羽玉（Lophophora williamsii f. caespitosa）

乌羽玉缀化（Lophophora williamsii f. cristata)

大型乌羽玉（Lophophora williamsii “var. texensis“)

Many thanks to the Cactus Conservation Institute and to the assorted cultivators who permitted me the opportunity to acquire these photographs!

Plants associated with Lophophora williamsii

Posted on December 9, 2014 by admin

Flora associated with Lophophora williamsii in Texas

Yucca treculeana

Common vegetation in the Tamaulipan Brushland:

(AKA “chaparral” or “thorn scrub” or “desert scrub” or “scrub brush”)

Acacia amentacea (“black-brush acacia”) [Note 17], Castela texana (“amargoso”), Celtis pallida (“granjeno”), Karwinskia humboltiana (“coyotillo”), Leucophyllum frutescens (“cenizo”), Porlieria (Guaiacum) angustifolia (“guayacan”), Prosopis juliflora (“scrub mesquite”), Larrea tridentata (“gobernadora” or “creosote bush”) and Condalia obovata (“brazil”).
In south Texas, Peyote grows in association with Yucca, Opuntia spp., Opuntia leptocaulis (“tasajillo”) and Echinocereus spp. (“pitaya”).

In Starr county, both Echinocereus pentalophus (“lady’s fingers”) and the charming endemic dwarf, Coryphantha robertii, are not infrequently associated with it in those areas near Rio Grande City where C. robertii is distributed.

Peyote’s highest populations in Texas, now, is in those areas referred to by many people as “impenetrable thorny scrub”.
In the Chihuahuan Desert it occurs in both the subdivision classified by desert scrub such as Larrea tridentata, Prosopis laevigata and Flourensia cernua, and also in the subdivision characterized by desert scrub incorporating many plants such as Agave lechuguilla and Yucca spp.

Plants associated with Chihuahuan Desert peyote and the percentage of frequency of co-occurrence according to Anderson 1980:
Larrea tridentata (“creosote bush”) over 75%
Jatropha dioica (“leather plant”) 70%
Opuntia leptocaulis (“pencil cactus”) 70%
Prosopis laevigata (“mesquite”) 70%
Agave lechuguilla (“lechuguilla”) 50%
Echinocactus horizonthalonius (“eagle’s claw cactus”) 50%
Mammillaria spp. (“fish-hook” or “nipple cactus”) 50%
Flourensia cernua (“tarbush”) 50%
Acacia spp. (“acacia”) 40%
Condalia spp. (“lotebush”) 40%
Coryphantha spp. 40%
Neolloydia spp. 40%
Yucca filifera (“yucca”) 40%
Hamatocactus spp. 40%
Coldenia (Tiquilia) canescens less than 40%
Euphorbia antisyphilitica (“wax plant”) less than 40%
Koeberlinia spinosa (“crucifixion thorn”) less than 40%
(The percentages given by Anderson were obtained as the ratio of the number of peyote sites where Anderson found that particular plant species to occur compared to the total number of peyote sites that he investigated in his 1960 dissertation. (That ratio was converted to a percentage.) Those 10 sites were Chihuahuan Desert populations and most, but not all, of them were Lophophora williamsii. One was Lophophora diffusa and another population was later determined by Dr. Terry to be Lophophora koehresii.)

From:
Anderson 1980 pages 149-151
Morgan 1983
and personal observations.

Due primarily to the opportunity presenting itself, it was decided to attempt the photodocumention of as much of the associated flora as opportunity permitted. Seven sites containing Lophophora williamsii populations have been explored with this goal in mind during the course of other field work occurring in 2009-2014. Three of those populations were in Tamaulipan thornscrub (two in Starr County and one in Jim Hogg County) and four locales were in the Chihuahuan Desert (one each in Brewster, Presidio, Terrell & Val Verde). In six cases I was able to photograph the existing Lophophora population and the accompanying vegetation, and in the other I was only able to focus on acquiring imagery of Astrophytum asterias and companions, as time did not permit the inclusion of the nearby Lophophora williamsii population. Some additional photographs showing close-up details of plants were obtained on properties in Maverick, Starr and Hildalgo Counties were peyote was not found. Those form the basis of the preliminary survey that this listing & photo collection represents. The basis of the listing at the Cactus Conservation website is simple, if we could find an instance of a plant growing with or near peyote that note was added to the list. If the observed relationship was one of being a nurse plant that was noted. In only a very few cases is a plant listed as associated based on someone else’s reported observation. A simple listing of those species and a representative sampling of images is included here. For far more images visit the CactusConservation.com website.
This should be regarded as an in-progress work presently limited to a very small sampling of Texas populations.

Under Cercidium texanum in Starr County

At all seven of those sites just mentioned there were at least one Acacia species, at least one Condalia species, some nature of at least one crust community, an Echinocactus species, at least one Echinocereus species, Jatropha dioica, Koeberlinia spinosa, at least one Leucophyllum species, assorted lichens, a Mammillaria species, at least one Opuntia species, Opuntia leptocaulis and at least one Yucca species.
Castela texana, at least one Coryphantha sp, an Ephedra, Porlieria, a Prosopis, Schaeferia, a Tiquilia, a Thymophylla and a Viguiera were observed at all but one site each and may have been overlooked at those exceptions.
Agave lechuguilla, Euphorbia antisyphilitica, and Larrea tridentata were present at all four West Texas sites.
As should be expected, Agave lechuguilla, Euphorbia antisyphilitica, and Larrea tridentata were absent from all South Texas sites. Karwinskia humboldtiana was present at all South Texas sites that included Lophophora as well all of the additional properties we visited in South Texas that lacked any Lophophora.
Many other plants are also potential nurse plants and I may easily have missed spotting or capturing an image. Numerous plants were encountered that have not yet been identified.
Many additional species were anticipated that have thusfar been elusive; and no doubt many instances of companion plants are yet to be recorded.

with Viguiera stenoloba in Jim Hogg County

The photographic documentation project can be found online at the Cactus Conservation Institute website. It is still in mid-assembly and has much left to do but future work will continue to be added to these two pages at their website:

Flora associated with Lophophora williamsii in Texas

The Chihuahuan Desert of West (Trans-Pecos) Texas

The Tamaulipan Thornscrub of deep South Texas

Gochnatia hypoleuca in Jim Hogg County

South Texas: Tamaulipan thornscrub

(This is the biotic zone containing the South Texas Peyote Gardens)
Senegalia (Acacia) berlandieri
Vachelia (Acacia) rigidula
Acourtia runcinata
Astrophytum asterias
Atriplex spp.
Bahia absinthifolia
Calliandra conferta
Castela erecta var. texana
Celtis pallida
Cercidium texanum
Colubrina texensis
Condalia hookerii
Condalia spathulata
Cordia boissieri
Coryphantha robertii (now lumped with Escobaria emskoetteriana)
Coryphantha macromeris var. runyonii
Croton humilis
Croton incanus
Croton spp.
Dalea sp.
Dolichothele (Mammillaria) sphaerica
Draba cuneifolia
Echinocactus texensis
Echinocereus enneacanthus
Echinocereus pentalophus
Echinocereus poselgeri
Echinocereus reichenbachii var. fitchii
Eysenhardtia texana
Ephedra antisyphilitica
Euphorbia (Chamaesyce) spp.
Gochnatia hypoleuca
Hamatocactus setispinus
Isotoma spp.
Jatropha dioica
Hedeoma drummondii
Heliotropium curassavicum
Hibiscus martianus
Karwinskia humboldtiana
Koeberlinia spinosa
Krameria ramosissima
Lantana achyranthifolia
Lepidium austrinum
Leucophyllum frutescens
lichens (many)
Lindheimera texana
Lippia graveolens
Mammillaria heyderi
Manfreda spp.
Melampodium spp.
mosses (occassional not typical)
Nama hispidum
Oenanthera laciniata
Opuntia engelmannii var. lindheimeri
Opuntia leptocaulis
Palafoxia texana
Parthenium hysterophorus
Parthenium incanum
Pennisetum ciliare
Pithecellobium flexicaule
Polanisia dodecandra
Porlieria angustifolia
Prosopis glandulosa
Prosopis reptans
Salvia ballotaeflora
Schaefferia cuneifolia
Sclerocactus megarhizus
Spermolepis echinus
Suaeda tampicensis
Thamnosma texana var. texana
Thymophylla pentachaeta
Thymophylla tenuiloba
Tidestromia lanuginosa
Tiquilla mexicana
Verbena quadrangulata
Viguiera spp.
Xylothamia palmeri
Zexmenia (Jeffea) brevifolia
Zexmenia (Weddelia) hispida
Yucca treculeana

Euphorbia antisyphilitica & Agave lechuguilla in Presidio County

West Texas: Chihuahuan desert

Acacia berlandieri
Acacia greggii var. wrightii
Acacia rigidula
Acacia roemeriana
Agave lechuguilla
Aloysia wrightii
Ariocarpus fissuratus commonly near Lophophora but usually not together.
Aspicarpa hyssopifolia
Bahia absinthifolia
Baileyana multiradiata
Bernardia obovata
Bouteloua spp.
Buddleja marrubifolia
Calliandra conferta
Castella erecta var. texana
Celtis pallida
Ceanothus greggii
Condalia ericoides
Condalia species
Condalia warnockii
Coryphantha echinus
Coryphantha ramillosa
Coryphantha tuberculosa
crust communities (many)
Dalea formosa
Dalea jamesii
Dasylirion texanum
Echinocactus horizonthalonius – same comment as Ariocarpus fissuratus
Echinocactus texensis
Echinocereus coccineus (often in area but only occasionally together)
Echinocereus dasyacanthus (often found nearby but rarely together)
Echinocereus enneacanthus
Echinocereus pectinatus var. wenigeri
Echinocereus stramineus
Echinocereus viridiflorus russanthus
Ephedra antisyphilitica
Ephedra trifurca
Epithelantha bokei
Epithelantha micromeris
Euphorbia antisyphilitica
Ferocactus hamatacanthus
Forestiera angustifolia
Forestiera spp.
Fouquieria splendens
assorted grass species
Heliotropium torreyi
Jatropha dioica
Koeberlinia spinosa
Krameria bicolor
Larrea tridentata
Lesquerella spp.
Leucelene ericoides
Leucophyllum candidum
Leucophyllum frutescens
Leucophyllum minus
lichens
Lippia graveolens
liverworts
Lycium berlandieri
Lycium spp.
lycopods (clubmoss)
Mahonia (Berberis) trifoliolata
Mammillaria heyderi (common, often unclear which came first)
Mammillaria lasiacantha
Mammillaria meiacantha (nearby but not together)
Mimosa biuncifera
Mimosa spp.
Mortonia scabrella
Nerisyrenia camporum
Notholaena sinuata
Opuntia (Grusonia) aggeria
Opuntia camanchica
Opuntia engelmannii
Opuntia leptocaulis
Opuntia mackensenii minor
Opuntia rufida
Opuntia schottii
Opuntia sp.
Opuntia strigl
Petrogenia repens
Placidium lacinulatum
Porlieria (Guaiacum) angustifolia
Portulaca mundula
Prosopis glandulosa
Psora crenata
Ruellia spp.
Salvia ballotaeflora
Schaefferia cuneifolia
Sclerocactus uncinata
Selaginella lepidophylla
Selaginella spp.
Tecoma stans
Telosiphonia macrosiphon
Thamnosma texana var. purpurea
Thymophylla acerosa
Thymophylla pentachaeta
Tiquilia canescens
Tiquilia greggii
Tiquilia mexicana
Tiquilia sp.
Verbena sp.
Viguiera stenoloba
Yucca elata
Yucca reverchoni
Yucca thompsoniana
Yucca torreyi

Castella texanum in Terrell County

Mexico: A similar project is needed for the populations in Mexico. Due to the wide range of Lophophora in Mexico that will be a tremendous undertaking.

Bohata et al 2005 noted observing the following cactus species with Lophophora in Mexico:
Ariocarpus fissuratus
Ariocarpus fissuratus subsp. bravoanus
Ariocarpus fissuratus subsp. hintonii
Ariocarpus fissuratus subsp. lloydii
Ariocarpus kotschoubeyanus
Ariocarpus retusus
Ariocarpus retusus f. elongatus
Ariocarpus retusus subsp. scapharostroides
Ancistrocactus brevihamatus
Ancistrocactus scheerii
Ancistrocactus uncinatus
Ancistrocactus uncinatus subsp. wrightii
Astrophytum myriostigma
Astrophytum myriostigma subsp. columnaris
Astrophytum asterias
Astrophytum capricorne
Astrophytum capricorne f. major
Astrophytum capricorne f. minor
Astrophytum capricorne subsp. niveum
Astrophytum capricorne subsp. senile var. aureum
“and many others”

Observable in Cactus Conservation Institute photographs online:

Agave spp.
Castella erecta texanum
Coryphantha sp.
Dyckia sp.
Echinocactus platyacanthus
Echinocereus spp
Mammillaria spp.
Sclerocactus uncinatus
Stenocactus spp.
Thelocactus spp.
Tiquilia sp.
Viguiera sp
Other cacti

Lophophora williamsii seedling emergent from under the cover of Leucophyllum, Gochnatia & Acacia leaf litter in Jim Hogg County.

Lophophora williamsii

Posted on December 6, 2014 by admin

The new home for this page (with more images) is now at: http://sacredcacti.com/wp/blog/lophophora-williamsii/

Lophophora williamsii (Lemaire ex Salm-Dyck) Coulter

Charles Antoine Lemaire on Salm-Dyck‘s behalf (1845) Allgemeine Gartenzeitung, 13: 385-386, as Echinocactus williamsii.

John M. Coulter (1894) Contributions from the US National Herbarium, 3 (3): 91-132, as Lophophora williamsii.

Lophophora williamsii in Jim Hogg County, Texas

Peyote has experienced many names in its history but the important older ones to be familiar with are Echinocactus williamsii, its confused moonlight appearance as the brief-lived Anhalonium lewinii and as Anhalonium williamsii (outside of a brief period of problems produced among some ethnobotanists, chemists and pharmaceutists by the appearance of A. lewinii.)
More details are in the Anhalonium lewinii commentary.

Mescaline is present in highly variable amounts.

Lophophora williamsii echinata tuft Presidio County

A peyote “tuft” in Presidio County

Lophophora is known to mean “I bear crests” (in reference to the hairy tufts) [from the Greek; lophos: “crest” and phoreo: “I carry”. Pizzetti 1985].

Lophophora williamsii A peyote bearing its tufts in Jim Hogg County

A peyote bearing its “crests’ in Jim Hogg County

The name williamsii was said by Rümpler (in Förster 1885) to be in honor of C.H. Williams, who was said to have traveled in Bahia, Brazil.
According to David Hunt (2006), C.H. Williams was a former British ambassador to Bahia.
dict.leo.org disputes the certainty of this, offering instead Theodor Williams, a Vicar of Hendon with a large garden in Middlesex that was noted for its many cactus specimens.
dict.leo.org also noted that another claim exists asserting it was named for botanist J.W. Williams; the Williams they refer to appears to have been a botanist in the USA with an interest in forensic science so it makes no sense as a choice of whoever assigned the name.

A reader also brought to our attention a comment by Cels et al. 1841–1842 (p. 354) in which this species was noted as having been dedicated by Lemaire to a “Mr. Williams”, an avid amateur collector near Lourdes, France (“[…] zele amateur des environs de Loudres“). The connection of Williams to this plant was not included.

Any rationale underlying the specific name choice for any of those proposed names is unclear to this author. Cels seems to offer the most logical choice so it is puzzling that Rümpler, Hunt, Anderson and others would either miss or ignore his words.

Rümpler 1888 mentioned that its country of origin was still unknown at that time but Cels 1841–1842 had clearly indicated it as being from Mexico.

Salm-Dyck, Coulter & Schumann
They all look so serious.

The person who actually selected the name is also not clear. I would assume from the description and from the note by Cels that it was Charles Lemaire but there seems to be some question raised about that.

Among the many names worn by the peyote plant, one is particularly convoluted. It was for a time commonly known as Anhalonium lewinii due to a strange twist of fate caused by a drug company, a handful of botanists, a couple of pharmaceutical chemists and a following of unquestioning ethnobotanists. See a detailed discussion and references herein under Lophophora diffusa and, more pointedly, under Lophophora lewinii.

See also Anderson 1980, Bruhn & Holmstedt 1974 or Ott 1993.

Lophophora williamsii echinata in Terrell County

Lophophora williamsii echinata sensu Weniger in Terrell County, Texas

Common names used for or names applied to peyote

Description & characteristics of Lophophora williamsii

Occurrence & Distribution of Lophophora williamsii

Human uses of peyote

Archaic peyote, some beans and a rock

Flora often associated with Lophophora williamsii

Analysis reported for Lophophora williamsii

Peyote Music & Icaros

Inquisition Law

Endnotes

Starr County

Lophophora williamsii analysis

Posted on November 28, 2014 by admin

This article, & the book Sacred Cacti, is best viewed at http://sacredcacti.com/blog/lophophora-williamsii-analysis/ My apologies for any 404 pages that may exist as the transfer is completed.

An interesting objection to peyote cultivation has been raised based on the assertion that peyote in cultivation may not express all of the alkaloids reported from wild plants. Something which was missed in this claim is that relatively few alkaloids have been reported from wild peyote and the majority, including all of the known trace alkaloids, were found using elaborate gc-ms trapping experiments and other approaches intended to capture short-lived intermediates and trace alkaloids. All of those studies used peyote plants which had been grown from seed and cultivated in greenhouses, primarily in northern Europe. rather than wild harvested plants.

Reported analysis of Lophophora williamsii

Mescaline content of Peyote

As is true for the alkaloid level of any plant, the mescaline content of peyote exists as a range that is influenced by at least several factors. The following simply summarizes the literature. Only some type of actual analysis or bioassay can say something accurate concerning a plant in front of a viewer. Literature should be viewed with caution and regarded to be only guidelines suggesting potential values.

“Arthur Heffter, a German pharmacologist of the nineteenth century estimated that there are about 4.6 to 5.8 grams of mescaline in every kilogram of dried peyote.” (Anderson 1980)
Heffter reported a maximum recovery in his work of 6.3% mescaline, 5.3% anhalonidine, 3% anhalonine, 0.5% lophophorine, 5.3% anhalamine.
Späth later reported having much lower yields working with old material.

Mescaline has been reported from L. williamsii with a min and max value of 0.10% and 6.3%. A range of 0.9-6.0% by dry wt is what is generally given. [Anonymous 1959, Heffter 1896a, Lundström 1971b, Martin & Alexander 1968, McLaughlin & Paul 1967 & Siniscalco 1983);
Anderson 1980 cited Kelsey 1959 (0.9%), Bergman 1971 (1.5%), Fischer 1958 (3%), Heffter 1896a (4.6-5.6 %[-6.3%])

Crosby & McLaughlin 1973 commented that mescaline content in dried peyote can reach 6% but rarely exceeds 1% in dried whole plant.

6% appears in Anderson, Kapadia & Fayez, Lundström 1971b, Martin & Alexander 1968, and Reti 1950. These are all second-hand accounts of that 6% value; referring to its publication by Heffter.

0.1% dry wt is the lowest value in the literature; reported in Siniscalco Gigliano 1983.

Ott 1993 estimated 2.4-2.7% mescaline by dry weight (~400 mg. per 16 grams of dried cactus) citing Bruhn & Holmstedt 1974 and Lundström 1971b.

Friends with extraction experience found fresh plants to average 0.2% mescaline from fresh plants and 1-2% from dried material. This refers to peyote originating from South Texas during the mid-1970s. This work was always done under fairly primitive and inefficient conditions. 2% is usually cited as an estimate in counterculture drug manufacturing literature. (50 grams of dried peyote per gram of mescaline recovered.).

Recently, a meme of “1% max” has been circulating; perhaps reflecting the current decrease in the average age and size of harvested plants due to careless overharvesting and harvest practices?

75-125 mg of HCl was recovered from 70-140 gm plants greenhouse grown in northern Europe. Lundström & Agurell 1971b (This approaches 0.1% by fresh weight; ; 0.1 to 0.2% by fresh weight is a commonly reported range.) [Also in Habermann 1978a & 1978b (from Štarha nd)]

Mescaline has been reported to comprise around 30% of the total alkaloid content of L. williamsii: Lundström 1971b.

Container grown plants in Italy were reported to contain 0.255% by fresh weight (2.55 mg/gm fresh was an average value derived from two specimens; estimated using HPLC). They also reported an average of 1.75% by dry weight. (Ed.: Note the obvious discrepancy)
Gennaro et al. 1996;

As L. williamsii var. typica Croizat:
0.709% (± 0.032) dry wt. Habermann 1978a (from Štarha 1997)

Variations across range:

Starr Co.: 2.77%;
Jim Hogg Co: 3.2%;
Val Verde Co: 3.5%;
Presidio Co: 3.52%.
(Averaged % by dry weight: – Used batched samples.
Hulsey et al. 2011.

Regrowth:

3.80% mature crowns,
2.01% small regrowth crowns (4 year after the prior harvest).
(Jim Hogg Co. Averaged % was by dry weight: – Used batched samples.)
Kalam et al. 2012 & 2013.

Batched samples were used to deliberately create an average value and lessen the possible contribution from potential high or low outliers. Comparison of Hulsey with Klein’s paper shows the wisdom in choosing that approach even if it does deprive us of an understanding of the max/min values. The ideal approach is a screening using batched plants followed by a more detailed look at a set of the individuals.
One peer reviewer suggested that batching in Kalam invalidated their results, which if true would invalidate the results of almost all published analytical work appearing in the history of phytochemistry. Almost all workers analyze multiple individuals to minimize the influence of potential outliers, the only actual difference between the acceptable approach of those workers (including in the same journal) and what was complained about with Hulsey or Kalam is the earlier workers did not REFER to their batched samples as being a batched sample.

Distribution in the peyote plant

Janot claimed to have established that mescaline was largely produced in the peripheral green parenchyma of the crown. As this was during the 1930s the identification would have been established using microchemical methods.

Todd 1969 found mescaline in the tops to be substantially greater than in the roots (using co-TLC). (See Note B)

Anonymous 1959, citing Rouhier 1927 “Le Peyotl”, gives the following percentages of alkaloid content in different parts of the cactus (% by dry weight unless otherwise stated):
Upper slices dried 3.70%
Lower slices dried 3.43%
[The above refers to the practice sometimes employed of horizontally sectioning the top of the cactus into two parts prior to drying.]

Peyote head dried 3.14%

Fresh peyote head 0.41%
Roots dried 0.73%
Fresh roots 0.244%

A closer look using 13 individual plants divided into three parts (crown, stem & root) that were then each analyzed separately:
1.82-5.50% in crown tissue,
0.125-0.376% in subterranean stem tissue,
0.0147-0.0520% in root tissue.
(Starr Co.; Analyzed individually. All % by dry wt.)
Klein et al. 2013 & 2015.
Notice that there is an order of magnitude decrease from crown to stem and again from stem to root?

Growth conditions

Siniscalco Gigliano 1983 reported his isolation of mescaline as:
0.10% from well irrigated plants,
0.93% from his grafted plants, and
up to 2.74% dry weight after 6 months of dry conditions.
All from peyote plants being cultivated in Italy.

Dried plant is said to have 3% Roland Fischer but Fischer claimed that only if chewed well or ground finely can this be extracted. He presented a study as indicating that less than one percent is obtained by chewing and swallowing. While finely grinding or chewing well is important for obtaining the best possible absorption (especially if using dry material) it must be pointed out that Fischer’s reasoning had some problems.
Fischer was able to get 3% mescaline from dried peyote by grinding it to a powder before beginning his extraction procedure. He found that if this dry grinding was omitted and the buttons rehydrated by soaking in water for two hours and then ground before extraction he could only recover 1%.
He went on to conclude “The only safe conclusion would be that the chewing of peyote and the swallowing as a bolus are certainly less thorough extraction procedures than our “wet grinding” procedure which recovers only about 1% of mescaline.”There several major flaws in Fischer’s reasoning and procedure, in so far as applying it comparatively to humans.
The more trivial of the two concerns Fischer basifying the buttons after soaking in water and then grinding, filtering, washing and adjusting the pH to 3.4 to 4.
In the stomach the chewed buttons are repeatedly macerated and massaged by peristaltic contractions in a dilute but fairly strong solution of hydrochloric acid (normally pH 1.5 to 2.5) which converts the rather poorly soluble mescaline base into the exceedingly water soluble mescaline hydrochloride. This means that the acidity used in human in vivo extraction is several orders of magnitude greater than that used by Fischer. (The effects of the digestive enzymes in the stomach do not contribute much as they consist primarily of pepsin which is specific for proteins.)
A more significant point was Fischer’s choice of base. When recovering 3%, he had used sodium hydroxide to bring it to pH 8.6, which is nearing the lower limit for good mescaline extraction as the free base. (97% at pH 8.6 according to Woods et al. 1951; 100% extraction is said to occur at pH 9 or above.). When he recovered 1%, for some reason he had decided to use sodium carbonate instead. This base is a good choice for many alkaloids. (It would have been acceptable if, for example, he was isolating DMT.) His bringing the pH to 8.8 might have enhanced his yield a trivial amount but mescaline has a tendency to form an insoluble carbonate, whether the carbonate source is in air or solution. This may have decreased his yield. [This may also have caused Reti some loss with Trichocereus terscheckii as well. This is just a hunch as rigorous evaluation has not been conducted. I should add that the presence of CO2 is also said to be critical for crystallization of mescaline to occur; according to LaBarre 1989.]
Although in agreement with the idea that chewing well or fine grinding is important to the best absorption, any direct comparisons of his findings to human rates of internal utilization need questioning.
While direct measurements of internal absorbence may not be possible, it would be feasible to administer known dosages of mescaline and subjectively compare them with known amounts of mescaline in cactus material. If a series of such bioassays were performed using experienced users a rough estimation could be determined which would be at least as accurate as Fisher’s extrapolation. It may also be possible to determine the percent of absorbence by monitoring the initial rise in blood levels during the early stages. This also would require the use of pure mescaline to establish a baseline. It also would require repeated evaluations using both different and the same individuals to be certain that biochemical individuality did not affect the results.

There are two additional accounts in the literature that are important to be aware of:

Sasaki et al 2009 and Aragane et al. 2011 published details from an interesting study of Lophophora demonstrating that genetic and chemical differences exist between L. williamsii and L. diffusa.

They additionally included three specimens of L. fricii but apparently renamed it based on what they found in publications by Edward Anderson, by Yoshio Ito & by H. Hirao. Aragane presented it to be a nonmescaline variant of L. williamsii. Earlier, Sasaki had said they had reidentified it as L. williamsii var. decipiens.
It is clear without any doubt that those three specimens were Lophophora fricii.

Aragane noted them to differ from their Lophophora williamsii:
1) by the word grey appearing only in the descriptions of their body color and not in those of any of their L. williamsii,
2) bearing large protuberences on the epidermis rather than small ones,
3) 2 of the 3 were noted to have a darker pink flower,
4) The primer sets were different from all of their L. williamsii (and closer to what was noted for diffusa),
5) They were purchased identified as Ginkangyoku (which is the Japanese trade name for L. fricii).

I’ll quote from those two papers as their contained comments provide more than adequate support for my line of reasoning:

“We identified the materials according to Anderson’s morphological classification.” Sasaki et al 2009.
The pertinent point being that Anderson recognized both Habermann’s Lophophora fricii (and wild plants he had encountered of Lophophora koehresii) to be L. williamsii. His view that only two species exist (L. diffusa and L. williamsii) is the basis for Aragane & Sasaki’s name assignment.

“Although the presence or absence of mescaline can easily be checked by chromatography, it is difficult to identify the species because not all L. williamsii contain mescaline. Chemotaxonomic identification of L. williamsii seems insufficient. DNA sequences of chloroplast trnL intron region in Lophophora plants were revealed to be beneficial for identification and showed a good correlation with mescaline content.” Sasaki et al. 2009.

“These samples were identified as L. williamsii in this study but were identified as L. williamsii var. decipiens in the literature.” [citing two illustrated cactus books by Y. Ito and by H. Hirao) Sasaki et al. 2009

“Interestingly, although Lo-14, Lo-15, and Lo-16 were identified as L. williamsii in this study, these three samples were also identified as L. williamsii var. decipiens in previous literature. 16,18
Sequence alignments in the trnL intron region of those three samples were different from those of Lo-2 to Lo-11. Moreover, another study of ours revealed that Lo-14, Lo-15, and Lo-16 contained no mescaline (Table 1). Using this method, we can distinguish mescaline-containing Lophophora plants from mescaline-free ones if the reaction is stopped at 65 min.”
Sasaki et al. 2009 (Lo-14, Lo-15, and Lo-16 were their Lophophora fricii specimens. Lo-2 through Lo-11 were all L. williamsii.)

“morphology of Lo-14 to 16 was similar to that of L. diffusa (Lo-17 to 20).” Aragane et al. 2011

“It was reported that L. williamsii contained mescaline, but that L. diffusa did not [15, 16]; however, it was unknown whether that L. williamsii was within the wide classification that included L. fricii. In this study, we clarified for the first time that there are two groups of L. williamsii, one with mescaline (group 1) and the other without it (group 2), and that L. diffusa contained no mescaline.” Aragane et al. 2011

It is fascinating that they did not grasp that they had just produced might could be considered to be adequate proof that L. fricii merited recognition as a species separate from L. williamsii rather than being considered to be a nonmescaline form of L. williamsii.

Aragane et al. 2011 reported mescaline concentrations in their Japanese horticultural specimens to range from 1.27-4.83%. (The concentrations reported for those 13 averages to 3.2%.) This is a range AND an average value that is quite comparable to what has been reported from wild plants.

Their presented sources produced some questions. In Sasaki et al. 2009 their plants were said to have been obtained from the “Medicinal Plant Garden, Tokyo Metropolitan Institute of Public Health“. In Aragane et al. 2011, most were listed as having been acquired through the “Internet” with all of the remainder coming from “Market (Mie Pref.)“.
Whether Aragane’s comments on dates and sources referred to the origin for the plants that Sasaki listed as being from the “Medicinal Plant Garden, Tokyo Metropolitan Institute of Public Health” or if Aragane’s comments were intended as a correction to Sasaki is not made clear.

These are the results from Aragane et al. 2011 concerning their specimens that were actually Lophophora williamsii:

#	Mescaline	Name	Date	Source
Lo-1	3.72%	Ubatama	4-2005	Internet
Lo-2	4.83%	Ubatama	4-2005	Internet
Lo-3	2.22%	Ubatama	1-2005	Market (Mie Pref.)
Lo-4	4.27%	Ubatama	1-2005	Market (Mie Pref.)
Lo-5	3.85%	Ubatama	1-2005	Market (Mie Pref.)
Lo-6	2.62%	Ubatama	4-2005	Internet
Lo-7	3.82%	Ubatama	4-2005	Internet
Lo-8	2.46%	Ubatama	4-2005	Internet
Lo-9	2.94%	Ubatama	4-2005	Internet
Lo-10	3.07%	Ubatama	4-2005	Internet
Lo-11	3.54%	Ougataubatama	4-2005	Internet
Lo-12	2.5%	Kofukiubatama	3-2005	Internet
Lo-13	1.27%	Ougataubatama	4-2005	Internet

Alkaloid content of Peyote:

Of the total alkaloid content:
30% is present as mescaline; 17% as pellotine.
Schultes & Hofmann 1980: 221.

Total alkaloid reported:
8.41% in dried “buttons”;
0.47% in fresh whole plants;
0.2% in fresh roots
0.93% in fresh tops.
Bruhn & Holmstedt 1974.
See more farther below.

Lewin was the first to isolate an alkaloid from peyote but it turned out to be both inactive entheogenically and a mixture of several alkaloids.

Heffter isolated 3 alkaloids from Lophophora williamsii and published his results and pharmacology in 1898. He named the active compound mescaline; determining it to be the active alkaloid by personal bioassays. [Heffter 1898a] Heffter named the other two alkaloids Anhalonidine and Lophophorine.

In 1976, 50 alkaloids had been observed;
(29 as substituted phenethylamines and 23 as tetrahydroisoquinolines):
Shulgin 1976 cited Kapadia & Fayez 1973

A total of 35 isoquinolines had been reported prior to 1986, according to Menachery et al. 1986.
The number of compounds now mentioned in the chemical literature as actually being detected in the plant is 72. Of which some are questionable inclusions, some are clearly errors and a number alkaloids still need a second-party confirmation by someone. At the moment the presence of 63 alkaloids has been established.
No doubt new trace alkaloids in peyote will continue to be found in the future so long as people devise more sophisticated techniques and/or continue to look for them.
It should be pointed out that any and all recent finds of alkaloids have been in trace quantities. Most have been identified using elaborate ‘trapping’ techniques for identifying short-lived biosynthetic precursors. Which also means it is a bit of a stretch to consider those components in the alkaloid fraction since normal extraction processes will not be able to recover them.
Any alkaloids discovered in the future will similarly be of purely biochemical interest rather than pharmacological contributors to the action of peyote.

In an incredible move suggested more than a small level of ignorance (and, at best, a serious lack of factual information), in 1997 Congress made law a provision declaring every alkaloid contained in peyote to be a Schedule One controlled substance.
Since several of these are normal components of human body fluids (including blood, CSF and urine) and many are present in a wide variety of plants, what this actually means remains to be seen.
It is more than a bit disconcerting that there are now AT LEAST a handful of normally present endogenous substances that are presently considered Schedule 1 (potentially as many as 9 different compounds); placing every human on the planet in measurable and perennial violation of US federal law.

According to Anderson 1980, Todd found little variation in the alkaloid concentration between roots and tops of plants except for hordenine which he found to be present only in the roots. This is misleading as stated.
Todd 1969 analyzed two populations of Lophophora williamsii (and also L. diffusa from Querétaro) collected during June, [a time considered to be poor for mescaline and good for isoquinoline effects.] His collections were made by Anderson near Monclova, Coahuila and El Huizache, San Luis Potosí.
Todd found lophophorine to be present at higher concentrations than mescaline in the plants collected from both locations. [It has been noted by other workers that N-Methylated compounds, such as Lophophorine, are higher during summer than winter. See below.]
Anhalamine and anhalonidine were present at nearly the same concentration as mescaline in plants collected in Coahuila and at the same concentration as mescaline in plants collected from San Luis Potosí.
Anhalonine and anhalinine were present at about half the concentration of mescaline in both populations.
While pellotine in the tops was present at lower concentrations than mescaline in the Coahuilan population, it was present at roughly equal concentrations to mescaline in the San Luis Potosí population.
Mescaline concentrations were found to be substantially higher in the population collected from Coahuila.
The difference in mescaline concentration between the roots and tops was found to be far greater in plants from San Luis Potosí than Coahuila. The mescaline concentration in the roots of Coahuilan plants was equal to the concentration of mescaline in the tops of the San Luis Potosí originating plants. Only traces of mescaline were observed in the roots of the San Luis Potosí originating plants (the Texas ‘Peyote Gardens’ population is believed to be similar).
Pellotine was found to be equally distributed between roots and tops in both populations but was present in higher amounts in the San Luis Potosí population.
Anhalamine, anhalonidine, and anhalonine were found to be equally distributed between roots and tops and were present in similar concentration in both populations.
Anhalinine and lophophorine were found to be equally distributed between tops and roots in the population at San Luis Potosí and less concentrated in the roots of those from Coahuila. Concentration in the tops of both populations were the same.
I suspect that it was the collection during June that caused the marked differences between his results and those of other investigators. A similar examination should be made using collections taken at two month intervals during December through mid-May, the usual time of indigenous people’s collection for use. The isoquinoline content proportional to mescaline, as reported by Todd, is far higher than is normally mentioned in the literature. [All of Todd’s concentrations were estimated by co-tlc with known amounts.]
The Coahuilan population is considered to be a stronger variety or even a separate species by some. Chemically there may be justification for this [Note 21] and it should be targeted for propagation. Plants originating from the Texas “peyote gardens” are believed to be similar to the San Luis Potosí population.
Todd’s descriptions do not allow comparison with the published descriptive differences between var. williamsii and var. echinata.
Lundström 1971b reported that the N-methylated alkaloids (such as Lophophorine) were highest during summer in greenhouse maintained plants. N-Demethylated compounds were found to be higher in fall and winter than N-methylated derivatives.
This corresponds well to Peyote using peoples traditionally gathering plants from November through April or mid-May (actual period of harvest varying from group to group but largly falling within this time frame with thre being at least one group of Huichols harvesting in October) and also with subjective observations that December through early March are the times for the best psychological effects and the least somatic distress. I believe that January and February are the most ideal months of the year.

Siniscalco 1983 reported that keeping cultivated peyote plants under arid conditions for 6 months substantially increased their mescaline content. Their corresponding reported values differed as 0.1% compared to 2.74% by dry wt. That is a 27.4X difference which is highly significant as taking a plant from fresh to total dryness only increases the concentration ~10X.

In whole fresh plants of L. williamsii, a total alkaloid content of 0.47% was found. (Of this 60% was present as phenolic alkaloids and 40% as nonphenolic alkaloids.)
The fresh roots had a total alkaloid content of 0.20% (67% phenolic/ 33% nonphenolic). The fresh tops had a total alkaloid content of 0.93% (58% phenolic / 42% nonphenolic)
Plants were harvested in ?? (they mentioned that L. diffusa was harvested in June).
[They added that Lundström 1971b found 0.4% total alkaloids in whole plants of which 57.5% was phenolic and 42.5% was nonphenolic alkaloids.]

Analysis of old materials

Dried peyote buttons, freshly prepared, had a total alkaloid content of 8.41% (64% phenolic versus 36% nonphenolic).
87 year old peyote buttons (sent to Watson by Rusby in 1887) had an alkaloid content of 8.86% (65% phenolic and 35% nonphenolic).
The mescaline content of the 87 year old buttons was much less than the new ones but they did not have enough variables to account for the difference. Only minor differences were observed with regards to most of the other alkaloids. Anhalinine was also markedly lower in the old material. Hordenine and 3-Hydroxy-4,5-dimethoxyphenethylamine were almost completely lacking from the old material. The latter of these had been noted earlier by both Späth 1922 and Agurell & Lundström 1968 as being rather unstable.
Bruhn & Holmstedt 1974

Percentages of alkaloids reported in peyote:

Ott 1993 gave a nice summary; citing Bruhn & Holmstedt 1974 and Lundström 1971b:
8% Total alkaloids in dried peyote buttons, of which:
30% is mescaline (= 2.4-2.7%) (~400 mg. per 16 grams of dried cactus)
17% is pellotine (peyotline) (= 1.4-1.5%)
14% anhalonidine (= 1.2-1.3%)
8% anhalamine (= 0.6-0.7%)
8% hordenine (= 0.6-0.7%)
5% lophophorine (= 0.4%)

Alkaloid percentages according to Kapadia & Fayez 1973.
References cited are theirs. (All percentages of total alkaloid content are from Lundström 1971)

Mescaline 6% (30% of total alkaloid content.)
Anonymous 1959

Pellotine (peyotline) 0.74% (17% of total alkaloid content.)
Heffter 1894b [This may have been from L. diffusa.]

Anhalonidine 5% (14% of total alkaloid content.)
Heffter 1896a

Anhalamine 0.1% (8% of total alkaloid content.)
Heffter 1901
(Späth & Becke 1935b also reported 0.1%.)

Lophophorine 0.5% (5% of total alkaloid content.)
Heffter 1896a

Anhalonine 3% (3% of total alkaloid content.)
Heffter 1896a

Anhalinine 0.01% (0.5% of total alkaloid content.)
Späth & Becke 1935a & 1935b

Anhalidine 0.001% (2% of total alkaloid content.)
Späth & Becke 1935a & 1935b

Hordenine 0.004% (8% of total alkaloid content.)

N-Methyl-4-hydroxy-3-methoxyphenethylamine (<0.5% of total
alkaloid content.)

N,N-Dimethyl-4-hydroxy-3-methoxyphenethylamine (0.5-2% of total alkaloid content.)

3-Demethylmescaline (1-5% of total alkaloid content was found in fresh material by Lundström & Agurell 1971)

N,N-Dimethyl-3-demethylmescaline (0.5% of total alkaloid content.)

N-Methylmescaline 0.002% (3% of total alkaloid content.)

O-Methylanhalonidine (<0.5% of total alkaloid content.)

Isopellotine (0.5% of total alkaloid content.)

Peyophorine (0.5% of total alkaloid content.)

Isoanhalidine (trace)

Isoanhalonidine (trace)

Isoanhalamine (trace)

Tyramine (trace)

N-Methyltyramine (trace)

Epinine (trace)

3,4-Dimethoxyphenethylamine (trace)

3,4-Dihydroxy-5-methoxy-phenethylamine (trace)

N-methyl-3-demethylmescaline (trace)

[All others found by other workers were also trace components.]
For more information on isolations and dates see elsewhere here.

Lundström 1971b found a total alkaloid content of 0.4% w/w to be present in the fresh buttons and noted that 0.41% had been determined by Rouhier (as cited by Anonymous 1959).

First pharmacological study of peyote was published in Lewin 1888a & 1894a.

An Abbreviated Chronology of the Identification of the Peyote alkaloids

The first report of alkaloids in peyote was the laboratory report of F.A. Thompson at Parke-Davis but Lewin was the first to publish. (Bruhn & Holmstedt 1974)

1888
Anhalonine (crystalline but not a pure compound)
Lewin (1888) Naunyn-Schmiedebergs Archiv fur Experimentelle Pathologie und Pharmakologie, 24: 401-411

1894
Pellotine This probably was from L. diffusa rather than L. williamsii. [The source of Heffter’s material is not known as this apparently came from German collectors with no identification of locality. Considerable trade of peyote collected from the locality of L. diffusa existed in early times and it was not differentiated from L. williamsii so it is probable that pellotine was not actually isolated from L. williamsii by Heffter. He referred to the material in this analysis as Anhalonium williamsii rather than A. lewinii, the latter being his source of mescaline below. See Bruhn & Holmstedt 1974 or the A. lewinii discussion herein.]
Heffter (1894)b Berichte der Deutschen Chemischen Gesellschaft, 27: 2975-2979.

1896
Anhalonidine
Lophophorine
Mescaline
Heffter (1896)a Berichte der Deutschen Chemischen Gesellschaft, 29: 216-227.

1899

Anhalamine

Kauder (1899) Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft, 237: 190-198.

1935
Anhalinine
Späth & Beck (1935) Berichte der Deutschen Chemischen Gesellschaft, 68 (3): 501-505.
Anhalidine
Späth & Beck (1935) Berichte der Deutschen Chemischen Gesellschaft, 68 (5): 944-945.

1937
N-Methylmescaline
Späth & Bruck (1937) Berichte der Deutschen Chemischen Gesellschaft, 70 (12): 2446-2450.

1938
N-Acetylmescaline
Späth & Bruck (1938) Berichte der Deutschen Chemischen Gesellschaft, 71 (6): 1275-1276.

1939
O-Methylanhalonidine
Späth and Bruck (1939) Berichte der Deutschen Chemischen Gesellschaft, 72 (2): 334-338.

1965
Hordenine
McLaughlin & Paul (1965) Journal of Pharmaceutical Sciences, 54 (4): 661.<
(Confirmed in McLaughlin & Paul 1966 Lloydia, 29 (4): 315-327.)
See Todd 1969 Lloydia, 32 (3): 395-398.

1966
Tyramine
N-Methyltyramine
Candicine (Identified by tlc. Presence in peyote is in question, see Kapadia et al. 1968 Journal of Pharmaceutical Sciences, 57 (2): 254-262.)
McLaughlin & Paul (1966) Lloydia, 29 (4): 315-327. (In addition to hordenine)

1967
Peyonine
Kapadia & Shah (1967) Lloydia, 30: 287. (Proceedings.)
See also Kapadia & Highet (1968) Journal of Pharmaceutical Sciences, 57: 191-192

1968
3-Hydroxy-4,5-dimethoxyphenethylamine
Agurell & Lundström 1968 The Chemical Society, London. Chemical Communications, 1638-1639.
(Confirmed by Kapadia et al. (1969)a Journal of Pharmaceutical Sciences, 58 (9): 1157-159.)
N-Acetylanhalamine
N-Acetylanhalonine
N-Acetyl-3-hydroxy-4,5-dimethoxyphenethylamine
N-Formylanhalamine
N-Formylanhalinine
N-Formylanhalonidine
N-Formylanhalonine
N-Formyl-3-hydroxy-4,5-dimethoxyphenethylamine
N-Formylmescaline
N-Formyl-O-methylanhalonidine
Mescaline maleimide
Mescaline malimide
Mescaline succinamide
Mescalotam
Peyoglutam
Kapadia & Fales (1968)a The Chemical Society, London. Chemical Communications, 24: 1688-1689.
Peyophorine
Kapadia & Fales (1968)b Journal of Pharmaceutical Sciences, 57 (11): 2017-2018, and Kapadia & Fales (1968)a The Chemical Society, London. Chemical Communications,24: 1688-1689.
Anhalotine (as iodide)
Choline
Lophotine (as iodide)
Peyotine (as iodide)
Kapadia et al. (1968) Journal of Pharmaceutical Sciences, 57 (2): 254-262.
3,4-Dimethoxyphenethylamine
Lundström & Agurell (1968) Journal of Chromatography, 36 (1): 105-108.

1969
Peyoxylic acid
Peyoruvic acid
Kapadia et al. (1969) Paper presented at the 116th Meeting of the American Pharmaceutical Association, Montreal, Canada. May 18-22, and Kapadia et al. (1970)b Journal of the American Chemical Society, 92 (23): 6943-6951.

1970
Mescaline citrimide
Mescaline isocitrimide lactone
Kapadia & Fales (1970)a Lloydia, 33 (4): 492. (Proceedings.) (Paper presented at the “11th Annual Meeting of the American Society of Pharmacognosy (Vienna, Austria) July 1970)”
Peyoglunal
Kapadia et al. (1970)a Lloydia, 33 (4): 492. (Proceedings.)

1971
Mescaloxylic acid
Mescaloruvic acid
Kapadia et al. (1971) Paper presented at the 118th Meeting of the American Pharmaceutical Association, San Francisco, California, March 27-April 2. “Some newer synthetic cactus alkaloid analogs.” and Kapadia and Hussain (1972) Journal of Pharmaceutical Sciences, 61 (7): 1172-1173.
Dopamine (3,4-Dihydroxyphenethylamine)
Epinine (N-Methyl-3,4-dihydroxyphenethylamine)
4-Hydroxy-3-methoxyphenethylamine
N-Methyl-4-hydroxy-3-methoxyphenethylamine
N,N-Dimethyl-4-hydroxy-3-methoxyphenethylamine
N-Methyl-3,4-dimethoxyphenethylamine
3,4-Dihydroxy-5-methoxyphenethylamine
Lundström (1971) Acta Chemica Scandinavica, 25 (9): 3489-3499.
N,N-Dimethyl-3-hydroxy-4,5-dimethoxyphenethylamine
N-Methyl-3-hydroxy-4,5-dimethoxyphenethylamine
Lundström (1971) Acta Pharmceutica Suecica, 8: 485-496.

1972

6,7-Dimethoxy-8-hydroxy-3,4-dihydroisoquinolinium inner salt

1,2-Dimethyl-6,7-dimethoxy-8-hydroxy-3,4-dihydroisoquinolinium inner salt
1-Methyl-6,7-dimethoxy-8-hydroxy-3,4-dihydroisoquinoline
2-Methyl-6,7-dimethoxy-8-hydroxy-3,4-dihydroisoquinolinium inner salt
Fujita et al. (1972) Yakugaku Zasshi, 92 (4): 482-489
Isoanhalamine
Isoanhalidine
Isoanhalonidine
Isopellotine
Lundström (1972) Acta Chemica Scandinavica, 26 (3): 1295-1297.

1973
O-Methylpeyoxylic acid
O-Methylpeyoruvic acid
Kapadia et al. (1973) Journal of Heterocyclic Chemistry, 10 (1): 135-136.

1977
Pellotine determined to exist in optically active form in the cactus. (This had been an unresolved question for many years due to rapid and ready racemization)
Cymerman Craig et al. (1977) Journal of the American Chemical Society, 99 (24): 7996-8002.

1996
Serotonin was claimed; using ion-interaction HPLC. Its identity was never actually proven and it was not isolated. It presently lacks confirmation.
Gennaro et al. (1996) Analytical Letters, 29 (13): 2399-2409.

2008
3,4-Methylenedioxyphenethylamine (Homopiperonylamine)
3-Methoxy-4,5-methylenedioxyphenethylamine (Lophophine)
N,N-Dimethyl-3,4-methylenedioxyphenethylamine (Lobivine)
These three compounds were reported but this needs to be taken with caution as their actual isolation and characterization was never performed. All identifications relied entirely on the spectral data of the extracted alkaloids and their corresponding derivated forms. The actual presence of these alkaloids still needs to be independently confirmed. A number of comments from this paper also need questioning, especially concerning their peculiar speculative assertions of their contributions to activity and their baseless allusions to MDMA or designer drug activity. (It was incredibly entitled “Ecstacy analogues found in cacti.” as if the activity of MDMA analogs did not require alpha substitution.) In a personal conversation, shortly after the appearance of this paper, Shulgin described the inclusion of his name as an author to be an “embarassment“.
Bruhn et al. (008) Journal of Psychoactive Drugs, 40 (2): 219-222.
Shulgin had however voiced his anticipation, in PIHKAL, that someday someone WOULD find 3-Methoxy-4,5-methylenedioxy-phenethylamine in a cactus and that it was a surprise that it had not been reported already.

Mrs. Anna B. Nickels, a long-time collector of cacti, is generally given credit for bringing peyote to the attention of Parke-Davis. [Safford 1908 is the first source I can find which claims this.]
Slotkin 1955 dismisses this on three counts:
1) Parke, Davis and Co. was unable to find any records concerning Mrs. Nickels,
2) Peyote from Parke, Davis and Co. was used by Lewin, and was said by both sources to have originated in Mexico; Mrs. Nickels lived in Laredo.
3) Mrs Nickels referred to peyote as mescal buttons.
Slotkin presented some circumstantial evidence that J.R. Briggs may have been the one who brought peyote to the attention of pharmaceutical science:
1) Briggs’ brother lived in Mexico and supplied him with peyote.
2) Park, Davis’ files on peyote begin with a clipping of a Briggs article.
3) Both Lewin and Briggs used the unusual name of muscale buttons.

Mrs. Nickels did bring the fact of this plant having medicinal use among native people to the attention of John M. Coulter (around 1892-3). She referred to them as “mescal buttons”.
It might be added that Mrs. Nickels had a large cactus exhibit in Chicago’s 1893 Colombian Exposition and was noted by Liberty Hyde Bailey as having published the first catalog of cacti published in the US (as the price list issued for her cactus retail business ~1876)
A couple of points arise concerning the claims of Slotkin; neither of which am I able to resolve:
Omer C. Stewart was furnished (By G.A. Bender) with a copy of a letter that Mrs. Nickels had sent to Parke-Davis and Company in Detroit dated 11 July 1888.
In this letter, she referred to Anhalonium Williamsii as Piotes.
Bender 1969 presents a somewhat different spin on the same account and presents Parke-Davis as becoming aware of mescal buttons due to reading J.R. Briggs’ published account of his ingestion. In Bender’s account, Briggs was contacted by Parke-Davis and requested to procure some mescal buttons on their behalf, which he eventually accomplished. Interestingly, Parke-Davis apparently lacked any understanding of the nature of their source plant so they sought outside help at identification. One of the dried buttons they had mailed to Lewin in Germany is what ended up in Hennings’ hands and became Anhalonium lewinii.

Effects of peyote summarized

See more details under Mescaline pharmacology (in the book PDF Part C The Cactus Alkaloids) or briefly in the following section.
Perhaps the best summation of peyote’s overall effects to-date was made in 1940 by Richard Evans Schultes:
“Because of the physiological activity of these constituents of the cactus, peyote is capable of inducing an intoxication which is characterized by a feeling of ease and well-being, by control of the limbs and senses, by absence of violence, and occasionally by visual and auditory hallucinations and abnormal synaesthesiae. There are seldom uncomfortable after-effects among users. As a result of this remarkable type of intoxication, peyote has come to be regarded by many Indians as the vegetal incarnation of a deity.” (page 177)
“The sustaining and stimulating properties of Lophophora Williamsii which enable the user to do an excessive amount of work without feeling fatigue are hardly separable from those properties which may be called curative.” (page 178)

Prentis_Morgan_Anhalonium_HCl_fig3_2wide

Anhalinine HCl crystals from Prentis & Morgan

Pharmacological overview of the non-mescaline alkaloid content of peyote

No hallucinogenic activity has yet been demonstrated for any peyote alkaloid other than mescaline. [There is one mention of hallucinations experienced with a very large dosage of pellotine and at least one claim of a hallucinogenic experience resulting from the ingestion of L. diffusa but they stand in contrast to all other observations.]
Pharmacology of mescaline and more details concerning the rest of the alkaloids can be found in the book PDF Part C The Cactus Alkaloids. Only a relative few of the peyote alkaloids are mentioned in this section.
Those listed have some nature of activity or lack of activity reported in the literature. Other alkaloids present in peyote, such as anhalinine are unlikely to contribute substantially, if at all, to its effects. This is due to their inactivity pharmacologically and/or, most often, to their extremely low concentrations.

Anhalamine

Found to be hardly active as anticonvulsant, tranquilizer or muscle relaxant by Brossi et al. 1966

Anhalidine

Found to be hardly active as anticonvulsant, tranquilizer or muscle relaxant by Brossi et al. 1966

Anhalonidine

Probably does not contribute to the pharmacology as it is one fourth as active as pellotine. Shulgin 1973
Heffter found doses of 20-25 mg of the hydrochloride produced narcosis in frogs followed by increased excitability. Complete paralysis was produced by larger dosages. A curarizing effect was caused by dosages of 30 to 50 mg. No significant effects were seen in mammals. Heffter 1898a
Said to produce slight sleepiness and a dull sensation in the head. LaBarre 1975 citing Rouhier’s Monographie pp. 227-232.
Found to be hardly active as anticonvulsant, tranquilizer or muscle relaxant by Brossi et al. 1966.

Anhalonine

Heffter 1898a found 5-10 mg injected into frogs produced an increase in the reflex excitability after a phase of paresis. Similar action was noted in rabbits but hyperexcitability was predominate. (Heffter also described other effects.)

Hordenine

Active as a stimulant [Bruhn & Bruhn 1973] but a 100 mg. dose was found by Heffter to be inactive. [Ott 1993] Hordenine may potentially contribute some activity as a norepinephrine reuptake inhibitor: Barwell et al. 1989. However, the extent of its actual contribution remains to be studied.
As Todd found this present only in the roots it may be doubtful that it contributes to the pharmacology of peyote although the claim from some users that they get mroe when eating the roots might merit evaluation. It is presently unknown whether the reported presence of hordenine in peyote buttons by other researchers reflects its occurrence in the tops during normal times of traditional harvest (perhaps before use as a biosynthetic precursor) versus Todd’s analysis occurring during June or whether it is due to the presence of roots or partial roots on the plants these other workers analyzed. (Some other workers did analyze WHOLE plants during their work.
See McLaughlin & Paul 1965, 1966 & 1967 and Rao 1970.
McLaughlin & Paul 1965 purchased their material from Penick.
McLaughlin & Paul 1965 was cited by McLaughlin & Paul 1966 for their procedure in processing the plants. In their 1966 work on biosynthesis they used plants obtained from Mexico which were maintained in a greenhouse.]
Found to cause paralysis of the CNS in frogs without previous excitation by Heffter 1894a.
Small doses have no effect on blood circulation but larger ones cause hypertension and accelerated pulse. Very large doses cause death by respiratory arrest.
Pressure effect is not of central origin but is due to stimulation of cardiac muscle. [Rietschel 1937a & 1937b]
Less active than adrenaline, more similar to ephedrine than adrenaline.
Other researchers reported a nicotine like action [Raymond-Hamet 1933a, 1933b & 1939 and Ludueña, as cited in Reti 1959]
Large doses decrease or reverse the hypertensive action of adrenaline. [Raymond-Hamet 1936]

Reported highly antiseptic and to have inhibiting effect on some soluble ferments. [Camus 1906a-d]
Comments partially adapted from Kapadia & Fayez 1970

The antibacterial and wound healing reputation of peyote and other cacti has been attributed to the presence of hordenine. See:
McCleary 1960 who studied the effects of a water soluble crystalline material extracted from peyote, which they named peyocactin, in vitro on 18 penicillin resistant strains including Staphylococcus aureus and Staphylococcus pyogenes. It inhibited all strains.

McCleary & Walkington 1964 found inhibitory effects in vivo on
mice inoculated with toxic strains of S. aureus. Found that other cacti were effective on some strains but none were as widely effective as peyote.
Rao 1970 showed that peyocactin and hordenine were identical.
Hordenine has well known antibacterial properties and was generally assumed to be the reason for the bacterial inhibition observed by McCleary above. It should be noted that in spite of peyote’s greater activity in this regard, other cacti they evaluated have been found to have higher hordenine contents. While most people have assumed that the activity is due solely to hordenine, this suggests that the matter is not yet cut and dried and some study might be worthwhile.
McLaughlin & Paul 1966 also found in vitro antibiotic activity against a broad range of microorganisms but were unable to document any significant in vivo activity.

Effects of Lophophorine on blood pressure in a cat (Dixon 1899)

Lophophorine

“…is highly toxic and produces strychnine-like convulsions at 12 mg./kg. doses but it produces nausea in human being at much lower doses.“ [Ott 1993 citing Anderson 1980]
Heffter 1898a “found a 20 mg. dose of lophophorine to produce vasodilation and headache.” [Ott 1993]
Shulgin 1973 & 1976 noted that all toxicity data and the assertions of its “highly toxic” nature is based on animal studies and human evaluations limited to Heffter’s single published report.
Administration of the alkaloid was said to produce an accentuated sickening feeling in the back of the head after 15 minutes, accompanied by hotness, blushing of the face and a slight slowing of the pulse. The effects are said to disappear after 40 minutes. [LaBarre 1975 citing Rouhier’s Monographie 227-232 who was referring to Heffter.]
Heffter found that 0.25-1 mg of injected hydrochloride produced a lengthy tetany in the frog. The increased excitability may last for several days but the animal recovers. (He noted no apparent action on the isolated frog heart.)
In rabbits hyperexcitability and accelerated respiration were noted at 7 mg/kg. Tetany was induced at 12.5 mg/kg and death at 15-20 mg/kg.
Intravenous injection of 2.5 mg increases blood pressure but higher doses are hypotensive, lacking a specific action on the heart. [Heffter 1898a]

Pellotine

Sedative effects at 50 mg. levels in adult humans. From Ott 1993
Temporary convulsion were caused in frogs, dogs and cats by dosages of 5-10 mg. [Ott 1993 citing Heffter 1898a]
Said to reduce the pulse by approximately a quarter in about an hour. Reported to cause heaviness of the eyelids, sensation of fatigue and an aversion to all physical and mental effort. [LaBarre 1975 citing Rouhier’s Monographie pp. 227-232]
Believed by some to be useful in man as a relatively safe narcotic. [Kapadia & Fayez 1970 referred to authors cited by Joachimoglu & Keeser 1924]
It was found to be hardly active in animals as anticonvulsant, tranquilizer or muscle relaxant by Brossi et al. 1966

Sasha Shulgin & out-of-this-world friends circa 2003

Sasha Shulgin & three out-of-this-world friends circa 2003

Alkaloids identified in peyote

More than 70 alkaloids have been published in the literature but some of those are clear errors, others have been questioned or lack confirmation. Only around 63 of those are actually confirmed.
Candicine and O-methylpellotine are disputed, the first as other workers were unable to identify it and the second as it apparently is in L. diffusa but not L. williamsii.
One could also question 1,2-Dimethyl-6,7-dimethoxy-8-hydroxy-3,4-dihydroisoquinolinium inner salt as it was was identified entirely by UV and comparison with similar structures.
The following list was organized after Anderson but has been updated and expanded to include a summation of the available reports for each alkaloid.
For physical data: please see the book “The Cactus Alkaloids”

Mono-oxygenated phenethylamines:

Tyramine

tlc
McLaughlin & Paul (1966) Lloydia, 29: 315.
(0.001% dry wt: McLaughlin & Paul 1966; trace: Lundström 1971a.
Also in Habermann 1978b (from Štarha nd)

N-Methyltyramine

tlc, mp, mmp, ir
McLaughlin & Paul (1966) Lloydia, 29 (4): 315-327.
(0.012% dry wt: McLaughlin & Paul 1966; trace: Lundström 1971a.

Hordenine

tlc, mp, mmp, ir
McLaughlin & Paul (1965) Journal of Pharmaceutical Sciences, 54 (4): 661.
(Confirmed in McLaughlin & Paul (1966) Lloydia, 29 (4): 315-327.)
(0.6-0.7% dry wt: Lundström 1971b; (0.008% dry wt.) McLaughlin & Paul 1966; Todd 1969 found it only in roots (tlc).
[Also in Habermann 1978b (from Štarha nd)]
[8% of total alkaloid content: Lundström 1971b]

Candicine

(tlc) Presence in peyote is in question
McLaughlin & Paul (1966) Lloydia, 29: 315-327. (Suspected presence based on tlc.)
Kapadia et al. 1968 could not confirm. Found other quaternary alkaloids but were unable to find candicine. Nor could Davis et al. 1983

Dioxygenated phenethylamines:

Dopamine

glc, gc-ms<
Lundström (1971)a Acta Chemica Scandinavica, 25 (9): 3489-3499
(trace: Lundström 1971a)

Epinine

glc, gc-ms
Lundström (1971)a Acta Chemica Scandinavica, 25 (9): 3489-3499
(trace: Lundström 1971a)

4-Hydroxy-3-methoxyphenethylamine

(3-Methoxytyramine)
glc, gc-ms
Lundström (1971)a Acta Chemica Scandinavica, 25 (9): 3489-3499
(trace: Lundström 1971a)

N-Methyl-4-hydroxy-3-methoxyphenethylamine

glc, gc-ms
Lundström (1971)a Acta Chemica Scandinavica, 25 (9): 3489-3499
(trace: Lundström 1971a; <0.5% of total alkaloid content: Lundström 1971b]

N,N-Dimethyl-4-hydroxy-3-methoxyphenethylamine

glc, gc-ms
Lundström (1971)a Acta Chemica Scandinavica, 25 (9): 3489-3499
(trace: Lundström 1971a; 0.5-2% of total alkaloid content: Lundström
1971b)

3,4-Dimethoxyphenethylamine

glc, gc-ms
Lundström & Agurell (1968) Journal of Chromatography 36 (1): 105-108.
(trace: Lundström & Agurell 1968 and Lundström 1971a. Also in Habermann 1978b: from Štarha nd)

N-Methyl-3,4-dimethoxyphenethylamine

glc, gc-ms
Lundström (1971)a Acta Chemica Scandinavica, 25 (9): 3489-3499
(trace: Lundström 1971a)

3,4-Methylenedioxyphenethylamine

(Homopiperonylamine)
HPLC
Bruhn et al (2008)
(Reportedly observed but lacking isolation & characterization and independent confirmation.)

N,N-Dimethyl-3,4-methylenedioxyphenethylamine

(Lobivine)
HPLC
Bruhn et al (2008)
(Reportedly observed but lacking isolation, characterization and independent confirmation.)

Trioxygenated phenethylamines and related amides:

3,4-Dihydroxy-5-methoxyphenethylamine

glc, gc-ms
Lundström (1971)a Acta Chemica Scandinavica, 25 (9): 3489-3499
(trace: Lundström 1971a)

3-Hydroxy-4,5-dimethoxyphenethylamine

(3-Demethylmescaline)
gc, gc-ms
Kapadia et al. (1969)a Journal of Pharmaceutical Sciences, 58 (9): 1157-1159.
Agurell & Lundström (1968) The Chemical Society, London. Chemical Communications, 24: 1638-1639.
(5% of total alkaloid: Agurell & Lundström 1968; 1-5% of total alkaloid content in fresh material: Lundström & Agurell 1971b. Also (identified) by Kapadia et al. 1969a and Agurell & Lundström 1968)

N-Methyl-3-hydroxy-4,5-dimethoxyphenethylamine

gc, gc-ms
Lundström (1971)c Acta Pharmaceutica Suecica, 8 (5): 485-496
(trace: Lundström 1971c)

N,N-Dimethyl-3-hydroxy-4,5-dimethoxyphenethylamine

gc, gc-ms

Lundström (1971)c Acta Pharmaceutica Suecica, 8 (5): 485-496

(0.04% dry weight i.e. 0.5% of 8% total alkaloid content: Lundström 1971c; 0.5% of total alkaloid content: Lundström 1971b)

N-Formyl-3-hydroxy-4,5-dimethoxyphenethylamine

(N-Formyl-3-demethylmescaline)
gc, gc-ms
Kapadia & Fales (1968)a The Chemical Society, London. Chemical Communications, 24: 1688-1689.
(trace: Kapadia & Fales 1968a)

N-Acetyl-3-hydroxy-4,5-dimethoxyphenethylamine

(N-Acetyl-3-demethylmescaline)

gc-ms

Kapadia & Fales (1968)a The Chemical Society, London. Chemical Communications, 24: 1688-1689.

(trace: Kapadia & Fales 1968a)

3-Methoxy-4,5-methylenedioxyphenethylamine

(Lophophine)
HPLC
Bruhn et al (2008)Lacking isolation & characterization. In need of confirmation.

Mescaline (3,4,5-Trimethoxyphenethylamine)

mp, mmp
Heffter (1896)a Berichte der Deutschen Chemischen Gesellschaft, 29: 216-227 (original isolation) but the structure was not actually determined until Späth (1919) Monatshefte fuer Chemie, 40: 129-154.
([0.10-]0.9-6.0[-6.3]% dry wt. has been reported [Note 22] [Anonymous 1959, Heffter 1896a, Lundström 1971b, Martin & Alexander 1968 & Siniscalco 1983);
Anderson 1980 cited Kelsey 1959 (0.9%), Bergman 1971 (1.5%), Fischer 1958 (3%), Heffter 1896a (4.6-5.6%[-6.3%])];
2.4-2.7 % dry (~400 mg. per 16 grams of dried cactus) Ott 1993 citing Bruhn & Holmstedt 1974 and Lundström 1971b
[Crosby & McLaughlin 1973 stated peyote can reach 6% but rarely exceeds 1% (dry wt.)]
[Tops>>Roots; Todd 1969 [Note 23]]
Siniscalco 1983 reported the isolation of 0.10% (well irrigated),
0.93% (grafted) and up to 2.74% dry weight (after 6 months of dry conditions) from plants cultivated in Italy; 0.1 to 0.2% by fresh weight is common

Friends with extraction experience found fresh Texas plants to average 0.2% during 1970s

75-125 mg of HCl was recovered from 70-140 gm plants greenhouse grown in northern Europe. Lundström & Agurell 1971b (This approaches 0.1% by fresh weight) [Also in Habermann 1978a & 1978b (from Štarha nd)] [30% of total alkaloid content: Lundström 1971b]

[As L. williamsii var. typica Croizat: 0.709% (± 0.032) dry wt.
Habermann 1978a (from Štarha 1997)]

N-Methylmescaline

mp, mmp
Späth & Bruck (1937) Berichte der Deutschen Chemischen Gesellschaft, 70 (12): 2446-2450.
(0.24% dry wt., 3% of total alkaloid: Lundström 1971b)

N-Formylmescaline

gc-ms
Kapadia & Fales (1968)a The Chemical Society, London. Chemical Communications, 24: 1688-1689.

(trace: Kapadia & Fales 1968a)

N-Acetylmescaline

mp, mmp
Späth & Bruck (1938) Berichte der Deutschen Chemischen Gesellschaft, 71 (6): 1275-1276.
Kapadia & Fales (1968)a The Chemical Society, London. Chemical Communications, 24: 1688-1689.
(trace: Späth & Bruck 1938 and Kapadia & Fales 1968a)

Tetrahydroisoquinolines and related amides:

Anhalamine

mp, mmp

Kauder (1899) Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft, 237: 190-198.
(0.1-0.7% dry wt. has been reported: Späth & Becke 1935b and Lundström 1971b; Also in Habermann 1974a (from Štarha nd); 8% of total alkaloid content: Lundström 1971b)

N-Formylanhalamine

gc-ms
Kapadia & Fales (1968)a The Chemical Society, London. Chemical Communications, 24: 1688-1689.

(trace: Kapadia & Fales 1968a)

N-Acetylanhalamine

gc-ms

Kapadia & Fales (1968)a The Chemical Society, London. Chemical Communications, 24: 1688-1689.

(trace: Kapadia & Fales 1968a)

Isoanhalamine

gc, gc-ms
Lundström (1972) Acta Chemica Scandinavica, 26: 1295-1297.
(trace: Lundström 1972)

Anhalidine

mp, mmp
Späth & Beck (1935)b Berichte der Deutschen Chemischen Gesellschaft, 68 (5): 944-945.
(0.001% dry wt: Späth & Becke 1935b; 0.16% dry wt. i.e. 2% of 8% total alkaloid content: Lundström 1971b)

Anhalotine (4° amine isolated as Iodide)

ir, nmr, uv
Kapadia et al. (1968) Journal of Pharmaceutical Sciences, 57 (2): 254-262.
(0.0003% dry wt: Kapadia et al. 1968)

Isoanhalidine

gc, gc-ms
Lundström (1972) Acta Chemica Scandinavica, 26: 1295-1297.
(trace: Lundström 1972 & 1971b)

Anhalinine

mp, mmp
Späth & Beck (1935) Berichte der Deutschen Chemischen Gesellschaft, 68 (3): 501-505.
(0.01% dry wt: Späth & Becke 1935b; 0.04% dry wt., 0.5% of total alkaloid content: Lundström 1971b)

N-Formylanhalinine

gc-ms
Kapadia & Fales (1968)a The Chemical Society, London. Chemical Communications, 24: 1688-1689.
(trace: Kapadia & Fales 1968)

Anhalonidine

mp, mmp
Heffter (1896)a Berichte der Deutschen Chemischen Gesellschaft, 29: 216-227.
(1.12% dry wt., 14% of total alkaloid content: Lundström 1971b; Also
in Habermann 1974a: from Štarha nd)

Pellotine

mp, mmp
Heffter (1894)b Berichte der Deutschen Chemischen Gesellschaft, 27: 2975-2979.
Kauder, E. (1899) Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft, 237: 190-198.
(±)-Pellotine
UV, IR, NMR
Kapadia et al. (1968) Journal of Pharmaceutical Sciences, 57 (2): 254-262.
(-) Pellotine
UV, CD
Cymerman Craig, J. et al. (1977) Journal of the American Chemical Society 99 (24): 7996-8002.
1.36% dry weight: Lundström 1971b;
Also (%?) Habermann 1974a, 1978a & 1978b: from Štarha nd;
17% of total alkaloid content: Lundström 1971;
As L. williamsii var. typica: 0.296% (± 0.065) Habermann 1978a: from Štarha in Grym 1997.

Peyotine (4° amine isolated as Iodide)

Pellotine methiodide
mp, UV, IR
Kapadia et al. (1968) Journal of Pharmaceutical Sciences, 57 (2): 254-262.
(0.00015% dry wt: Kapadia et al. 1968)

N-Formylanhalonidine

gc-ms
Kapadia & Fales (1968)a The Chemical Society, London. Chemical Communications, 24: 1688-1689.
(trace: Kapadia & Fales 1968a)

Isoanhalonidine

gc, gc-ms
Lundström (1972) Acta Chemica Scandinavica, 26: 1295-1297.
(trace: Lundström 1972)

Isopellotine

gc, gc-ms
Lundström (1972) Acta Chemica Scandinavica, 26: 1295-1297.
(0.04% dry weight, 0.5% of total alkaloid content: Lundström 1971b)

S-(+)-O-Methylanhalonidine

O-Methyl-d-anhalonidine
mp, mmp
Späth & Bruck (1939) Berichte der Deutschen Chemischen Gesellschaft, 72 (2): 334-338.
(0.04% dry wt., <0.5% of total alkaloid content: Lundström 1971b)

N-Formyl-O-methylanhalonidine

gc-ms
Kapadia & Fales (1968)a The Chemical Society, London. Chemical Communications, 24: 1688-1689.
(trace: Kapadia & Fales 1968a)

O-Methylpellotine

gc, gc-ms (using L. diffusa)
[Bruhn & Agurell (1975) Phytochemistry,14: 1442-1443.]
Presence in L. williamsii is in doubt. It is included by Mata & McLaughlin 1982 but they do not list individual references for the compounds.
Bruhn & Agurell believed that it is unique to L. diffusa but it was later it was found in Pachycereus weberi.
I am still reviewing Mata & McLaughlin’s references in case someone found this as a trace component in peyote but that does not presently appear to be likely. Štarha did not detect it in L. fricii or L. jourdaniana but DID report it in L. koehresii. Obviously Štarha’s work was not available to Mata & McLaughlin in 1982

6,7-Dimethoxy-8-hydroxy-3,4-dihydroisoquinoline

mp, UV, IR, NMR, MS
Fujita et al. (1972) Yakugaku Zasshi, 92 (4): 482-489.
(Journal of the Pharmaceutical Society of Japan)
(0.0008% fresh weight: Fujita et al. 1972; as L. williamsii var. caespitosa)

2-Methyl-6,7-dimethoxy-8-hydroxy-3,4-dihydroisoquinolinium inner salt

mp, uv, IR, NMR, MS
Fujita et al. (1972) , 92 (4): 482-489.
(Journal of the Pharmaceutical Society of Japan)
(0.001% fresh weight: Fujita et al. 1972: as L. williamsii var. caespitosa)

1-Methyl-6,7-dimethoxy-8-hydroxy-3,4-dihydroisoquinoline

mp, UV, NMR, ms
Fujita et al. (1972) , 92 (4): 482-489
(0.0001% fresh weight: Fujita et al. 1972: as L. williamsii var.
caespitosa)

1,2-Dimethyl-6,7-dimethoxy-8-hydroxy-3,4-dihydroisoquinolinium inner salt

UV
Fujita et al. (1972) , 92 (4): 482-489.
(0.00008% fresh wt: Fujita et al. 1972: as L. williamsii var. caespitosa)

Lophotine (4° amine isolated as Iodide)

ir, nmr, uv
Kapadia et al. (1968) Journal of Pharmaceutical Sciences, 57 (2): 254-262.
(0.0002% dry weight: Kapadia et al. 1968)

S-(-)-Anhalonine

S-(-)-Lophophorine

mp, mmp
Heffter (1896)a Berichte der Deutschen Chemischen Gesellschaft, 29: 216-227.
UV, IR, NMR
Kapadia et al. (1968) Journal of Pharmaceutical Sciences, 57 (2): 254-262.
(0.4% dry wt: Lundström 1971b;
0.5% dry wt: Heffter 1898c.
[Also in Habermann 1974a (from Štarha nd)]
5% of total alkaloid content: Lundström 1971b;
Appeared to be the major alkaloid in 2 sorts of summer collected plants: tlc by Todd 1969)

N-Formylanhalonine

gc-ms
Kapadia & Fales (1968)a The Chemical Society, London. Chemical Communications, 24: 1688-1689.
(trace: Kapadia & Fales 1968a)

N-Acetylanhalonine

gc-ms
Kapadia & Fales (1968)a The Chemical Society, London. Chemical Communications, 24: 1688-1689.
(trace: Kapadia & Fales 1968a)

Peyophorine

tlc, gc, ir, ms, mp
Kapadia & Fales (1968)b Journal of Pharmaceutical Sciences,. 57 (11): 2017-2018.
Kapadia & Fales (1968)a The Chemical Society, London. Chemical Communications, 24: 1688-1689.
(trace: Kapadia & Fales 1968a; 0.04% dry wt., 0.5% of total alkaloid content: Lundström 1971b)

Conjugates with Krebs Acids:

Peyoxylic acid

Kapadia & Fayez (1973) cites Kapadia et al. (1969) 116th Meeting of the American Pharmaceutical Association, Montreal, Canada. May 18-22. “Identification and synthesis of 3-demethylmescaline, a plausible intermediate in the biosynthesis of the cactus alkaloids.”
Kapadia & Fayez (1970) cited “Kapadia, Rao, Leete, Fayez, Vaishnav and Fales, to be published.” i.e. Kapadia et al. (1970)b Journal of the American Chemical Society 92 (23): 6943-6951.
(trace: Kapadia et al. 1970)

O-Methylpeyoxylic acid

mp, NMR
Kapadia et al. (1973) Journal of Heterocyclic Chemistry, 10 (1): 135-136.
(trace: Kapadia et al. 1973)

Peyoruvic acid

gc
Kapadia et al. (1970)b Journal of the American Chemical Society, 92 (23): 6943-6951.
(trace: Kapadia et al. 1970)

O-Methylpeyoruvic acid

mp, NMR
Kapadia et al. (1973) Journal of Heterocyclic Chemistry, 10 (1): 135-136.
(trace: Kapadia et al. 1973

Mescaloxylic acid

tlc, gc-ms, synthesis, NMR, MS
Kapadia & Hussain (1972) Journal of Pharmaceutical Sciences, 61 (7): 1172-1173.
Kapadia et al. (1971) 118th Meeting of the American Pharmaceutical Association, San Francisco, California, March 27-April 2. “Some newer synthetic cactus alkaloid analogs.”
(trace: Kapadia & Hussain 1972)

Mescaloruvic acid

Mescaline succinamide

gc-ms
Kapadia & Fales (1968)a The Chemical Society, London. Chemical Communications, 24: 1688-1689.
(trace: Kapadia & Highet 1968)

Mescaline malimide

gc-ms
Kapadia & Fales (1968)a The Chemical Society, London. Chemical Communications, 24: 1688-1689.
(trace: Kapadia & Fales 1968a)

Mescaline maleimide

gc-ms
Kapadia & Fales (1968)a The Chemical Society, London. Chemical Communications, 24: 1688-1689.
(trace: Kapadia & Fales 1968a)

Mescaline citrimide

gc-ms, and ir, nmr and ms of synthetic
Kapadia et al. (1970)a Lloydia, 33 (4): 492.
Kapadia & Fayez (1970) cite Kapadia et al. “11th Ann. Meet. Amer. Soc. Pharmacognosy (Vienna, Austria) July 1970, To be published.” i.e. Kapadia et al. (1970)a Lloydia, 33 (4): 492.
(trace: Kapadia et al. 1970)

Mescaline isocitrimide lactone

Peyoglutam

gc-ms
Kapadia & Fales (1968)a The Chemical Society, London. Chemical Communications, 24: 1688-1689.
(trace: Kapadia & Fales 1968a)

Mescalotam

gc-ms
Kapadia & Fales (1968)a The Chemical Society, London. Chemical Communications, 24: 1688-1689.
(trace: Kapadia & Fales 1968a)

Pyrrole derivatives:

Peyonine

gc, ms, ir, nmr, tlc, glc, uv, mmp, synthesis
Kapadia & Shah (1967) Lloydia, 30: 287. (Proceedings.)
Kapadia & Highet (1967) Lloydia, 30: 287-288 (Proceedings.)
Kapadia & Highet (1968) Journal of Pharmaceutical Sciences, 57: 191-192.
(trace: Kapadia & Highet 1968

Peyoglunal

gc-ms, ir, nmr, ms, color reactions, synthesis
Kapadia et al. (1970)a Lloydia, 33 (4): 492.
(trace: Kapadia et al. 1970)

Other alkaloids:

Choline

tlc, gc, ir
Strongly alkaline viscous liquid. 123 mg from 2.3 kg dried peyote.
Identified by mp and mmp of picrate and IR,
Kapadia et al. (1968) Journal of Pharmaceutical Sciences,. 57 (2): 254-262.
(0.005% dry wt: Kapadia et al. 1968

See Anderson 1980 pages 191-203 and Menachery et al. (1986) (THIQ); both have line drawings of structures. (See also Cactus Chemistry By Species)

Two other inclusions appear in some listings of peyote alkaloids:

N-(3,4,5-Trimethoxyphenethylamine)-alanine /h2>

[Synonym for Mescaloruvic acid; See Kapadia & Hussain 1972a]

N-(3,4,5-Trimethoxyphenethylamine)-glycine

[Synonym forMescaloxylic acid; See Kapadia & Hussain 1972a]

Do not confuse either compound with the
3,4,5-Trimethoxyphenethyl-glycine which Sethi et al. 1973 synthesized
for use as a reference standard but were unable to observe in the
plant.
[Note: 3,4,5-Trimethoxyphenylalanine
3,4,5-Trimethoxyphenethylglycine.]

Other compounds reported from Peyote

Serotonin was claimed in hplc by Gennaro et al. 1996. This identity was never conclusively proven and it has not been confirmed.

Glucaric acid (saccharic acid) (tlc by Kringstad & Nordal 1975).

Calcium oxalate (the forms and degree of hydration have not been established)
Users of fresh peyote have observed it as well due to it being readily perceived as sand or grit present inside of the flesh. Oxalate is sometimes present in appreciable quantities.

Rouhier 1926 observed the presence of oxalate crystals in his histological study of the plant. These are labelled “O” in the drawing below; “C” is said to indicate the shards created by the action of the microtome when making the thin section slice.
Oxalate appears to be present in the form of druses (whewellite?), crystal sand and as additional forms. Rouhier commented on “oursins d’oxalate de chaux [weddellite?] et vaisseaux spiralés” being present in the flesh in addition to “macies d’oxalate de calcium“.
Spiky crystals inside of cacti are often Weddellite (CaC₂O₄•2H₂O) and the rounded druses Whewellite (CaC₂O₄•H₂O) but the nature of the biominerals that exist inside of peyote flesh apparently remains unstudied. (Weddelite is extremely rare in nature outside of cacti biominerals and as a component of kidney stones but it is common in both of those.)

Alexandre Rouhier 1926
Monographie du Peyotl, fig. 26

Oxalate crystals in peyote’s flesh exposed by rodent activity

Biosynthetic studies

Studies and route proposals for mescaline and peyote alkaloids(s):

Agurell & Lundström 1968
Agurell et al. 1967
Basmadjian & Paul 1971
Battersby et al. 1967
Kapadia & Fayez 1970
Khanna et al. 1969
Leete 1959 & 1966
Lundström 1971a & 1971b
Lundström & Agurell 1968b, 1969, 1971 & 1972
McLaughlin & Paul 1967
Paul 1973
Paul et al. 1969a & 1969b
Reti 1950
Rosenberg & Stohs 1974 [Comparative utilization studies for tyrosine in protein and alkaloids biosynthetic pathways. They determined the utilization of tyrosine for incorporation into alkaloids is three times the rate of incorporation into protein.]
Rosenberg et al. 1967 & 1969

Peyote alkaloids other than mescaline:

Battersby et al. 1968
Kapadia et al. 1970b
Khanna et al. 1970 [Radiolabeled precursor incorporation studies.]
Leete & Braunstein 1969
Lundström 1971c & 1972 [the latter is not a biosynthetic study per se but does offer some supportive evidence]
McFarlane & Slaytor 1972a [A point on biosynthesis of anhalonidine] & 1972b [Biosynthesis of 3,4-Dimethoxyphenethylamine]

For a review of tetrahydroisoquinolines in peyote and other cacti see pp. 256-276 in:
Jan Lundström (1983) “Simple Isoquinoline Alkaloids.” pp. 255-327 (Chapter 6) in: Arnold Brossi (Ed.) The Alkaloids. Chemistry and Pharmacology. Volume 21.
See also:
Mary D. Menachery et al. (1986) Journal of Natural Products, 49 (5): 745-778. “Simple Isoquinolines” (for a review of physical data and distribution.)

Archaic peyote, the red bean & more.