Lophophora williamsii

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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

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.

Any rationale underlying the specific name choice for any of those proposed names is unclear to this author. Especially as Rümpler 1888 mentioned that its country of origin was unknown to him at that time.

people-Williamsii

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

The person who actually selected the name is also not clear. I would assume that would have been 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

 

Suggested reading on peyote

 

Peyote Music & Icaros

 

Inquisition Law

 

Suggested reading (rock art, entrainment & entoptic imagery)

 

Endnotes

 

Lophophora-williamsii-StarrCounty-1

Starr County

 

Lophophora williamsii analysis

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.

 

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)

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

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
(0.24% dry wt., 3% of total alkaloid content: Lundström 1971b)

 

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

gc

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

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)

 

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

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)

 

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

Alexandre Rouhier 1926
Monographie du Peyotl, fig. 26

Oxalate crystals in peyote's flesh exposed by rodent activity

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.

Peyote: the archaic, some beans and a rock

Archaic points of potential interest

See page 194 in Schultes & Hofmann 1980 concerning the claims of Adavasio & Fry 1976 related to archeological finds of peyote in rock shelters and caves in the Cuatro Cienegas Basin in Coahuila, Mexico.
This is a fascinating article that is often mentioned in conjunction with their proposal that, over the millennia, sacramental plants were progressively replaced by safer ones. While it is a tantalizing notion to entertain, it needs to be understood that Adavasio & Fry did not include adequate evidence to support either of their assertions a) that the use of Ungnadia preceeded that of Sophora and b) both were eventually replaced with Lophophora. Three points need to be made:
First, any evidence presented for the sacramental use of the Mexican Buckeye (Ungnadia speciosa Endl.) is circumstantial at best, being primarily based on its form of packaging being similar to that of the Texas mountain-laurel (Sophora secundiflora (Ort.) Lag. ex SD), their occasional comingling, and was bolstered with only one second-hand reference to it being a euphoric plant. There does not appear to be any accounts of or archaeological evidence for it actually being used for human ingestion ceremonially. This is not a small point to overlook.

Ungnadia speciosa leaves

Ungnadia speciosa leaves

archaic: Ungnadia speciosa seeds

Ungnadia speciosa seeds

Second, Sophora itself is not known to have ever actually been used as a sacramental hallucinogen per se. It was employed in a highly dangerous form of a vision quest to gain animal spirits as guardians, protectors or familiars. Granted, it was incorporated into the peyote drink as prepared by several tribes and it is reasonable to assume that to be an ancient practice. It has been closely associated physically with peyote rites, strung as beads, as well as reported to have been used medicinally, ritually and as a “narcotic” (a word that has been so misapplied, misconstrued and misused anthropologically as to have little, if any, reliably discernible meaning).

Sophora secundiflora flowers

Sophora secundiflora

Sophora secundiflora leaves

Sophora secundiflora

I do not dismiss Sophora‘s sacred stature, nor would I want to dispute its long association with the peyote ritual but it is important to keep in mind that its use (or effectiveness) as a hallucinogen has never been adequately demonstrated. It certainly is not supported by any of the published human bioassays involving either the plant or its pure alkaloids.
Descriptions of its effects were given years ago, in an upper division University of Texas at Austin anthropology class taught by Dr. William W. Newcomb (ANT 322M: “Indians of Texas”). Newcomb presented the stage of interaction with animal spirits to occur while the subject was in a deep coma-like stupor. Their successful entry into this state was said to demonstrated to onlookers by their unresponsiveness to a toothy gar-fish jaw being raked across their flesh. After intense headache, profuse vomiting and violent convulsions, a “coma” ensued that was said to last for several days. [That commentary is not included in his book Indians of Texas but rather was taken directly from my class notes.]

Sophora secundiflora seeds

Sophora secundiflora

Dr. Newcomb clearly presented it as being used ritually but not as a ritual sacrament or hallucinogen in the sense of peyote.
[See Schultes & Hofmann 1980 & 1992 for a broader discussion and also Hatfield et al. 1977 for chemical study and a discussion of the reports of ethnological use. LaBarre 1975 also includes a fascinating discussion.]
Ott 1993 mentions that despite claims by a number of people that the use of the ‘Red bean’ was the predecessor to and replaced by that of peyote, this was thoroughly challenged in a monograph by Merrill 1977.
I have had some very curious interactions with this plant; none of which involved its ingestion. It is definitely able to interact with people, and to a surprising degree to direct and influence their behavior to gather its seeds. I also believe it to be a sentient being based on my experiences with it as a living plant. It is not surprising that it was highly venerated by any people who knew it. It is also not surprising that they would gather its seeds in large numbers and store them in a special context. I’ve noticed that this still occurs although I am guessing modern containers of beans are maintained entirely for their decorative value.
Finally, my main objection to the conclusions of Adavasio & Fry concerning peyote is that they only selectively mention one solitary occurrence of the plant found by an earlier worker [Note 30].
It is very peculiar to attempt the support of such important conclusions with a single data point. Perhaps they also encountered additional examples but did not mention the details in this article. It is a puzzling omission considering their core assertion was one of safer plants being sequentially adopted.
Campbell 1958 had flatly asserted that it was not possible to demonstrate the priority of mescal beans over peyote based on the available evidence so something more is required.

It might also be added that there is a lack of evidence suggesting a continuity of culture in which a sequential series of sacramental replacements *could* occur but this seems trivial by comparison to items 1, 2 or 3.

No futher evidence was presented by Adavasio & Fry.
Disturbingly, the only find of peyote mentioned by Advasio & Fry in the same context as Sophora and Ungnadia was that of ONE string of dried peyote buttons dating from several millennia after peyote is known archeologically to have been employed by humans.
[See comments in Boyd & Dering 1996 concerning Ungnadia.]

The omission by Adovasio & Fry of any reference to additional finds is puzzling but it is far from being the only instance of cherry-picking that one can encounter in this area.
Schultes & Hofmann 1992 commented that peyote has been thought to have been in use for at least 4000 years. Dry cave and rock shelter finds in Texas are also said to have yielded dried samples of peyote that were three thousand years old and one find was purportedly dated to 7000 years. Those refer to specimens in the Witte Museum that have been claimed to be of that immense age (more on this in a moment.)
Oddly, until recently the entirety of the radiocarbon dating surrounding peyote has almost been characterized by missing information.
Let’s take a look at what is known concerning ancient peyote dating.
There are five reports where peyote was mentioned as being recovered from archaeological sites but material for only two of these can be located within the known collections. (See Terry et al. 2006 for details and references.)
One of these was from Cuatro Ciénegas, Coahuila, Mexico. This is a burial site from the transition between the Late Archaic and the Late Prehistoric Periods.
The account of Bruhn et al. 1978 gave its age based not on the actual dating of the peyote but on the dating of material thought to be associated with that single set of 8 strung and remarkably well preserved peyote buttons. Three mats had been dated with a range of 810-1070 AD (uncorrected values).
Due to the burial being a secondary interment, Martin Terry dated one of the actual Cuatro Ciénegas’ peyote specimens establishing its age as 835 ± 35 14C years BP.
Shumla Cave (No. 5, 41VV113) in southwest Texas on the other hand was an inhabited residential site (with intrusion of several burials.) The peyote was believed to have been deposited in the Eagle Nest subperiod of the Middle Archaic Period.
The exact provenience of the materials removed from the caves was not recorded but it is clear that they did mention recovering “a single mummified example” from Shumla Cave No. 5. This later became mistakenly presented as “petrified”. There was clearly more than one such artifact recovered from those excavations as three remained at the Witte for the removal of samples following the consumption of several others for earlier radiocarbon analysis. Terry et al. 2006 also reported their dating of the Shumla Caves’ peyote to 5195 ± 20 14C years BP.

 

Summary of earlier dating accounts:

Peter Furst was the first to report a date of 7000 BP for the Shumla cave material but due to several reasons the actual test data is either lost or irretrievable. It is therefore not possible to know anything further about the work or the claim. That claim oddly only appeared as a passing mention within a book review written by Furst. His date was repeated by Schultes & Hofmann and now appears stated as a fact throughout the literature.
Bruhn et al. 2002 presented a letter to the editor of Lancet in which they asserted establishing peyote use for 5700 years after dating the Shumla material (Furst’s 7000 BP). They repeated the claims in DeSmet & Bruhn 2003 citing Bruhn et al. 2002 as their primary reference.
El-Seedi et al. 2005 reported dating the Shumla Caves’ material to 3780-3660 BC.
Jan Bruhn (in a personal communication with Martin Terry) reported this was a weighted mean of 4952 ± 44 14C years.
Further investigation by Terry suggests that the discrepancy was most likely due to a failure of Bruhn to remove residual humic acid prior to radiocarbon dating. (See Terry et al. 2006)

Before leaving the subject of Sophora and Ungnadia completely, one point which must be considered is that world wide people have often venerated plants known to be deadly or exceedingly dangerous, with no intentions of using them for ingestion unless perhaps for the purpose of inducing death, or sometimes when ascertaining the guilt or innocence of a person by ordeal poisoning.
Many other ritual purposes besides hallucinogen use exist for plants. As the authors point out, the quantities found far exceed what would be needed for ingestion purposes. [Issue might be taken with their regarding a “crazed” state as being one conducive to, much less equated with, any ritual or sacred act. If anything it reflects a common culture-centric dismissal of what is viewed as a “more primitive” mindset.]
The most common usage of the red bean is that of ornamentation in the form of beads. The Mexican Buckeye would also make fine beads although none were mentioned as such.
Apparently the finds of both seeds consisted primarily of small caches of them, sometimes mixed together, which were sealed in plaited or twilled baskets which had to be torn to access the contents. [Both seeds also make a very nice sound, with good high frequency components, when shook or stirred. In quantity; the sound is absolutely mesmerizing. Such containers might have been musical instruments?]
In some sites, Sophora seeds and pods were found scattered throughout the cultural deposits.

Sophora-fruit-1 3

Sophora secundiflora seedpods

Those twilled containers could also represent power objects used just as they were. We know between almost nothing and nothing about these people’s religious and spiritual beliefs. Some people who later used the beans believed they needed to be roasted until yellow, or forcefully struck and crushed, to ‘kill’ them before use. Since the seeds recovered in those finds were apparently being stored intact perhaps they were intended to assure protection after death, or at least to be available after death.
It may be noteworthy however that in the Murrah Cave many of the individual Sophora seeds were described by Holden 1937 as being “parched”; perhaps indicating preparation for potential drug use. Alkaloids can sometimes be altered using heat so parching can be reasonably suspected to indicate preparation for some type of human use. It does not prove
It is not clear how many of these finds were in funerary context as was the case for the string of peyote and how many were found in residences (suggesting their employment by living people). The context can be complex as it is clear that burials occurred that intruded into older residential remains.
Their hypothesis is intriguing though; further work should be done to evaluate it even if it turns out to be a blind path.
A systematic review of the contents of rock shelter and cave excavations in the Chihuahuan Desert might prove a valuable avenue for anthropological studies of the religious and spiritual beliefs of people in this area before the invasion and occupation. The creation of small painted rocks and large pictoglyphs featuring shamanic themes are among the unique elements left by the archaic people who once lived around the mouth of the Pecos River.

 

A fascinating analysis was performed, by Bruhn & workers, on the aforementioned specimen of Cuatro Ciénegas peyote (the string of buttons) which was found by Taylor in 1941.
Bruhn et al. 1978 found 2.25% alkaloid in the Cuatro Ciénegas’ material in spite of it being thought to be from around 810 to 1070 AD. Their analysis was reported to show it to contain mescaline, lophophorine, anhalonine, pellotine and anhalonidine present in measurable amounts.
Phenolic alkaloids formed 35% of the total. It was noted that this is substantially lower than the 8% total alkaloid and 64% phenolic fraction which they observed in recently prepared peyote buttons.
They used tlc and GC (both with known reference samples) to determine this. See Bruhn et al. 1978 for more details.
A peculiar assessment was more recently presented by Bruhn et al. 2002, also DeSmet & Bruhn 2003 and also El-Seedi et al. 2005 where it was being noted that the total alkaloid content was lower in the far older Witte material from the Shumla Caves. They then went on to assert that while only 2% alkaloid was present there was no alkaloid other than mescaline that was detectable. That was intriguing enough but was not the end.

Bruhn then made the peculiar proposal that the reason they could only detect mescaline could be due to mescaline being more stable than the other peyote alkaloids. Reasonable enough on the surface yet it is noteworthy that in this Bruhn failed to mention any of his own previous work that contradicts this claim. Clearly something is in need of closer inspection. This claim about the Shumla specimens needs consideration in the light of his 1978 Cuatro Cienegas results. There was also his earlier report concerning degradation of peyote alkaloids in the study of 87 year old peyote buttons in Bruhn & Holmstedt 1974. In particular, their determination clearly showing that mescaline content apparently decreased *ahead* of the rate of decomposition of many of the other alkaloids. The cherry-picked selective presentation of facts in their 2002/2003/2005 account appear to have been overlooked by Bruhn’s peer reviewers or at least they dropped the ball in terms of what peer review is meant to accomplish. That is all actually fairly however when trivial compared to what they AND Bruhn’s crew missed.
The most interesting aspect of this so-called ‘mummified’ material in my mind is that, unlike Bruhn, Furst or Taylor, Terry & coworkers recognized that the specimens were not dried peyote buttons at all but rather were manufactured effigies of peyote created from some type of doughy material. (See images of both the Shumla and Cuatro Cienegas materials in Terry et al. 2006.)

Shumla_Terry_et_al_p1019_fig_3

Shumla peyote effigy

There are only the partial and hollowed out remains of three of these effigies are left due to the destructions of the rest of the materials during chemical analysis and radiocarbon dating. They were formed as a mixture of cactus materials combined with some sort of unidentified fibrous noncactaceous plant material and the resulting dough shaped by hand to vaguely resemble a living peyote cactus top. There was apparently at least two different makers of these artifacts over a period of some years as both their compositions and their dates varied. The most recently manufactured effigy had used entirely cactaceous materials.
More remarkable would be the assertion by Bruhn & coworkers that was just mentioned that this material contained 2% mescaline by weight *and* that only mescaline was detectable. Intriguing if true but in light of Bruhn & Holmsted previously establishing the deterioration of mescaline over time occurred at a faster rate than the deterioration of most of the other alkaloids I am left with far more questions than answers. It is obvious that we need to remain skeptical of Bruhn’s claim, no matter how intriguing it may be, as we proceed.
One thing that is clear, these ‘buttons’ were clearly manufactured artifacts. To be able to retain 2% mescaline after 5 millennia would require it to have once have had a far higher alkaloid content. The presence of ONLY mescaline would not be a result of some magical selective degradation process omitting mescaline but would absolutely require the involvement of some type of purification process. Or perhaps there are missing elements of this tantalizing puzzle that are presently defeating our understanding of exactly what has been established in these studies.
Did these prehistoric people really know of a route for purifying or at least greatly concentrating mescaline? It would certainly be interesting if true but establishing that Bruhn’s analytical results were actually valid has to be the starting point for answering this peculiar question and the burden of proof for establishing their validity is on the authors of that work.
Were these potent effigies a prepared drug form that were created for sacramental use rather than for simple use as effigies? No matter how they were prepared and no matter what their alkaloid content, they are clearly both deliberate and sophisticated in their preparation.
Or are Bruhn/El-Seedi/DeSmet’s reported analytical results simply needing to be questioned?

 

“Petrified” peyote buttons

The first reference to ‘petrified peyote’ was a misnomer in reference to the Shumla Caves’ adulterated & reconstituted 5 millennia old peyote effigies that were mentioned above. (See Terry et al. 2006 for details.)

More recently ‘petrified peyote buttons’ have been offered for sale (and finding at least one buyer) at a large southwestern Gem & Mineral Show and probably elsewhere.

petrified-peyote-front

Sold as petrified peyote button (front)

petrified-peyote-back

Sold as a petrified peyote button (back)

These do appear on first glance to vaguely resemble dried peyote buttons but are without a doubt either an agate or another form of chalcedony with a fine drusy quartz coating on one side. They lack the critical features (such as ribs, the distinctive apex and areoles) that are typically found in peyote buttons (see below).

Schultes 1937 peyote buttons

peyote buttons

They are amazing natural treasures but clearly are not of botanical origin.

Gymnocalyciums

 This section details only those gymnocalyciums that have been reported to contain mescaline. A more comprehensive treatment of the analytical accounts of the entire genus can be located within Cactus Chemistry By Species_2014_Light which also includes the analytical results listed below.
Some synonyms are included but in most cases the names have been left however they were analyzed as the lumping resulting from the mergers help to obscure some interesting chemistry. These are not being kept separated as an suggestion that they merit recognition, this practice is being employed simply to better preserve and illustrate the published chemical variances. Synonyms are also included so this should be found more helpful than not. Similarly in those analysis involving invalid names, the abandoned names are preserved a,s while those names may be invalid, the analytical results are meaningful as they actually analyzed horticultural plants that physically exist whether they have a good name or not.

 

Gymnocalycium species

 

Gymnocalyciums: Gymnocalycium fleisheranum

Gymnocalycium fleisheranum

 

Commonly called “Chin Cactus” due to the “chin” below each areole.
See examples above and below.

 

Gymnocalyciums: Gymnocalycium triacanthum

Gymnocalycium triacanthum

 

Fruit are typically oblong and red (see image at top of page).
Hortus Third. page 530.

Name is from the Greek:
gymnos “bare” and kalyx “bud”; for its bare flower buds.

 

Gymnocalyciums: Gymnocalycium triacanthum

Gymnocalycium triacanthum

 

See also Backeberg 1959 [3: 1695-1786] (includes many pictures.) and Britton & Rose 1922 [3: 152-166] (includes a number of pictures).

 

Only a representative sampling of the species listed have entries below.

 

Gymnocalyciums: Gymnocalycium asterium

Gymnocalycium asterium

 

A simple list of the mescaline containing Gymnos:

 Gymnocalycium achirasense Till. & Schatzl

 Gymnocalycium asterium Ito (now merged into G. stellatum)

 [Available varieties include:

     v. albispinum

     v. nigrispinum

     v. paucispinum

     v. roseiflorum]

 Gymnocalycium baldianum (Speg.) Spegazzini

 Gymnocalycium calochlorum (Bödeker) Y. Ito

 Gymnocalycium carminanthum Borth & Koop

     [var. minimum is also available.]

 Gymnocalycium comarapense Backeberg

 Gymnocalycium denudatum (L.&O.) Pfeiff.

 Gymnocalycium fleischerianum Backeberg (No reference was included)

 Gymnocalycium gibbosum (Haworth) Pfeiffer

 Gymnocalycium horridispinum Frank

 Gymnocalycium leeanum (Hook.) Britton & Rose

 Gymnocalycium mesopotamicum Kiessling

 Gymnocalycium monvillei (Lemaire) Br. & R.

 Gymnocalycium moserianum Schutz

          [var. laejera is also available.]

 Gymnocalycium netrelianum (Monville) Br. & R.

 Gymnocalycium nigriareolatum Backeberg

 Gymnocalycium oenanthemum Backeberg

 Gymnocalycium paraguayense Schutz

 Gymnocalycium quehlianum (Haage) Berger

   Available varieties include:

     v. albispinum

     v. flavispinus

     v. kleinianum

     v. nigrispinum

 Gymnocalycium ragonesii Castellano

 Gymnocalycium riojense Fric ex. H.Till. & W.Till 

 Gymnocalycium riograndense Cardeñas (now Gymnocalycium pflanzii subsp. zegarrae)

 Gymnocalycium stellatum Spegazzini

 Gymnocalycium striglianum Jeggle

 Gymnocalycium triacanthum Backeberg

 Gymnocalycium uebelmannianum Rausch

 Gymnocalycium valnicekianum Jajó (now Gymnocalycium mostii subsp. valnicekianum)

 Gymnocalycium vatteri Buining (now Gymnocalycium ochoterenae subsp. vatteri)

 

 A summary of the published chemistry can be found at the end of the Gymnocalycium examples below.

 

A handful of Gymnocalycium species:

 

Gymnocalycium baldianum  (Spegazzini) Spegazzini

Carlo Luigi Spegazzini (1905) Anales del Museo Nacional de Buenos Aires. Buenos Aires, ser. 2,  3, 4: 505. as Echinocactus baldianus.
Carlo Luigi Spegazzini (1925) Anales de la Sociedad Cientifica Argentina, 99: 135. as Gymnocalycium baldianum.

 

Gymnocalyciums Gymnocalycium baldianum

Gymnocalycium baldianum

 

Small amounts of mescaline reported.

Origin: Argentina (Andalgalá (mountains east of), Catamarca, Cuesta de Portezuelo, Cuesta de Totoral,Hualfin, Sierra Ancasti,Sierra Graciana, Sierra de Guayamba, Sierra de Narvaes, Sierra de Manchao) Collections have been reported from (500m-)900m-1700m(-2000m)

 Habitat: Among grasses. (IUCN citing Charles 2009)

86. Echinocactus Baldianus Speg. (n. sp.)

Diag. Hybocactus, parvus globoso -depressus, obscure snbcinerascente-viridis; costis 9-11 latis et obtusissimis, sulco acuto profundiusculo limitatis, fere in tuberculis solutis; areolis parvis: aculéis gracilibus saepius 5, ómnibus marginalibus radiantibus adpressis sordide pallideque ciñereis; floribus apicalibus erectis mediocribus extus obscure glauco-viridibus glaberrimis laxe squamosis, squamis sensim in phylla intense purpurea transeuntibis, laciniis stigmaticis brevibus 6 albo-ochroleucis. Speggazini 1905

Depressed-spherical body, to 7 cm in diameter and 10 cm tall. [Eventually to 3.5 inches in diameter; Anderson 1998]
Epidermis is dark greyish to bluish-green.
9-11 ribs, fewer at first, becoming more distinctly tuberculate.
5-7 pinkish-grey to horn-grey or ash-grey, radial spines. More or less appressed or directed laterally, somewhat darker below at first. Spines are weak and flexible; sometimes twisting.
No centrals.
[1.5 inch wide] flowers are variable; lighter or darker red to a more or less blood-red. [White, pink, orange, red or shades in between; borne in spring.
Flowering can occur for several months. Anderson 1998] Pilbeam notes flowers to be variable as pink through red but proposes that hybridization may be responsible for some of the color forms.
Flowers around Christmas in habitat.
Bears dark green elongated fruit.
Backeberg 1977: page 183.
Pilbeam 1995: pages 43-44,  fig 14.

Photos with flower: Anderson 1998: page 80 & Pilbeam 1995: plate 15.

Anderson 1998 claims flowering size (1.5 inches in diameter) can be reached in 12 months from seed and it will handle 10°F briefly.

Listed by IUCN as “Least Concern” as, despite a restricted range and pressure from collection activity, it has a continuous range. Local collection and fire are said to be the primary threats.
Perea, M. & Trevisson, M. 2013. Gymnocalycium baldianum. The IUCN Red List of Threatened Species. Version 2014.2. <www.iucnredlist.org>

 

External resources:

Cactus-Art

Gymnocalycium.free.fr

Gymnocalycium calochlorum  (Bödeker) Y.Itô

Friedrich Bödeker (1932) Monatsschrift der Deutschen Kakteen-Gesellschaft, 4: 260. as Echinocactus calochlorus.
Yoshi Itô in John Borg  (1952) Cacti, 90. as Gymnocalycium calochlorum.

 

Gymnocalyciums: Gymnocalycium calochlorum

Gymnocalycium calochlorum

 

Small amounts of mescaline reported.

Origin: Argentina (The original collection did not include a locality. Reported to occur at Cordoba, Nono, Villa Bura Borchero, La Mudana, Las Rabonas. Collections have been recorded from 900 and 1000m according to Pilbeam; 800-1500m according to IUCN.)

Habitat:  “often buried in crumbling granite, where it can be difficult to find if not in flower or fruit (Charles 2009). It grows in high-altitude grasslands and chaco forest.” IUCN

Cushion forming plant with depressed-spherical cushion-like single heads.
Bodies are grey-green to blue-green to around 6 cm diameter and to 4 cm high.
Around 11 tuberculate ribs with creamy-white felted round areoles.
Up to 9 closely set whitish to pale pinkish-brown radial spines that are thin, wispy, rough, appressed, more or less curving; to 9(-12.5) mm long. No centrals.
Pale pink flowers to 6 cm long, opening only moderately. Produced only from the youngest areoles. Petals are not revolute.
Floral tube is long and of a lighter green according to Backeberg or bluish according to Pilbeam.
Fruit is bluish-green and long-ovoid.
Backeberg 1977 page 184,
and Pilbeam 1995: pages 52-53, Photos as fig. 21 and plates 25 (flowering) & 26 (in habitat),
and Pizzetti 1985 entry #117 (includes picture)

Listed by the IUCN as a species of “Least Concern” due to a perception of it being locally abundant and resistant to disturbances.  The IUCN says both “It is very widespread…” and  “…the range is not particularly wide,…”
Demaio, P. & Trevisson, M. 2013. Gymnocalycium calochlorum. The IUCN Red List of Threatened Species. Version 2014.2.

 

Gymnocalyciums: Gymnocalycium calochlorum

Gymnocalycium calochlorum

 

Recognized varieties mentioned by Pizzetti (only the first is respected by Pilbeam):
 var. proliferum; with larger darker or glacous stems, flowers that open widely and flower segments that curve outward (may be
brownish-white, pink or white; often pink at base.)

 var. roseiacanthum; a smaller variety (half the size of the
species). Glaucous green with yellowish rounded areoles and contorted
pinkish spines. Flowers are large and white with red bases. These
plants occur in the Sierra de Córdoba.

Pizzetti recommends protection from intense cold and shady positions when the sun is hottest. Prefers cool weather.

 

External resources:

Cactus-Art

Gymnocalycium.free.fr

 

Gymnocalycium gibbosum (Haworth) Pfeiffer

Adrian Hardy Haworth (1816) Botanical Register; 2: 137. as Cactus gibbosus.
Louis Pfeiffer ex Ludwig Mittler (1844) Taschenbuch für Cactusliebhaber. Leipzig, 2: 124. as Gymnocalycium gibbosum.

 

Gymnocalyciums: Gymnocalycium gibbosum

Gymnocalycium gibbosum

 

Presence of mescaline reported but unconfirmed.

Origin: Southern Argentina. [Río Chubut, Río Negro and Chubul Provinces:
Lat. 40-45o S.; La Plata, Mendoza, San Luis] 

Pilbeam 1995 mentions the species as being widespread in Argentina “covering a great deal of Patagonia, the provinces La Pampa and Buenos Aires and as far west as Mendoza and reported from southern Argenia, at Chubut, Rio Negro and Santa Cruz; recently by Pilz from Argentina, Abra de la Ventura.” Collections have been reported from 400-500m.
The IUCN cites Hunt et al. 2006 as giving occurrences “at elevations of 0 to 1,000 m“.

Habitat:monte shrubland and patagonian steppe (estepa patagónica)” “likes the sandy or gravelly alluvial soil along the Río Negro and Río Colorado, where it grows under bushes and other plants (Charles 2009).” IUCN

gymnocalyciums: Haworth 1816 BotanicalRegister, 137, diagnosis of Cactus gibbosus

Haworth 1816 Botanical Register, 2: 137, Latin diagnosis of Cactus gibbosus

Solitary glaucous, dull or dark (bluish)green well-armed stems, (Pilbeam: dark green to blue-black or greyish-green”) later sooty or brownish-green, to 10 [-24] inches (12-15 cm) high and 6 inches (10-12 cm) thick. Starts
globular then becomes more cylindrical.

Areoles set 1.5-2 cm apart.
12-14 [-19] strongly tubercled, straight, notched and rounded ribs with lightly sunken round areoles with greyish (Pilbeam describes as brownish-cream) wool. Prominent chins below areoles. 
7-12 radial spines, stiff, spreading, needle-shaped to awl-shaped, typically straight but  may be slightly curved, and mostly brown. (or light brown with a reddish base.) Up to 3.5 cm long. Nearly spineless at apex.
Can have 1-3 central spines (0-6 according to Pilbeam) but usually they are absent. When present they are often not readily distinguishable from the radial spines.
White (to faintly pink or reddish) flowers to 2-1/2 [to 2-3/4] inches long (6 cm long opening to 6 cm wide). Inner petals are lanceolate. Petals shaded from white to pink. Stamens and stigma are white; stigma has 12 yellowish lobes.
Diurnal flowers in summer.
Produced a club-shaped short, dark-green fruit.
Seldom branches unless injured or grafted, but some varieties do branch freely.
page 530 in Hortus Third
and Backeberg 1977: page 186
and Borg 1937: page 239
and Innes & Glass 1991: page 127 [Includes
picture of flowers]

and Lamb & Lamb 1971: page 654
and Pilbeam 1995: pages 73-76, fig. 37 & 38, plate 47
and Pizzetti 1985 Entry #119. (has color photo)


Listed by IUCN as a species of “Least Concern” due to having no major threats and having a wide range in which it occurs abundantly.   ListedIts range includes protected areas.
Demaio, P. & Trevisson, M. 2013. Gymnocalycium gibbosum. The IUCN Red List of Threatened Species. Version 2014.2.

 

Gymnocalyciums: Gymnocalycium gibbosum

Gymnocalycium gibbosum

Hortus recognizes:
 cv. Ferox has more numerous spines

 cv. Nigrum has very dark spines

 cv. Schlumbergii has more numerous spines that are stiff pinkish red to amber yellow.

     page 530 in Hortus Third

 

Gymnocalyciums: Gymnocalycium gibbosum var. schlumbergii

Gymnocalycium gibbosum cv. Schlumbergii

 

Many varieties exist in both the wild and in cultivation. First described in 1812. Has been known by many names over the years due to its varieties.
 Entry #119 in Pizzetti 1985

Pilbeam 1995 mentioned that “Nearly 30 varietal names have been allocated to this species.”

 cv. Nobile is said to have a larger sperical stem and longer overlapping spines; white with red base.

 Borg 1977 mentions var. caespitosum Hort., var. ferox Lab., var. leucacanthum K.Schum., var. Schlumbergeri K.Schum., var. nobilis K.Schum., and var. leonensis Hildm.

 Backeberg 1977 mentions var. leucodictylon (K.Schum.) Y.Ito, var. nigrum Backbg, and var. nobile (Haw.) Y.Ito.

 var. rostratum is also commercially available. It is described as having a dark grey stem.

IPNI lists:

v. borthii

v. brachypetalum

f. cerebriforme

var cerebriformis

var. chubutense

ssp ferdinandii

ssp. ferox

ssp. gastonii

var. nigrum

ssp. radekii

ssp. radovanii

This has always been a popular plant and is widely grown.

Innes & Glass recommend indirect light and a 50°F minimum temperature.
Pizzetti describes it as cold tolerant but taking no frost, tolerant of heat and requiring some sun.
I’ve found it to be able to survive frost but typically scarring badly afterwards. In Texas,  it was repeatedly attacked by thrips.

[See also Backeberg 1959 [3: 1752-1755] (includes pictures of several varieties, also fig. 1687, page 1756 and fig. 1688, page 1757.) and Backeberg 1977 page 186 and Britton & Rose 1922 [3: 158-159] (picture in fig. 166 page 157.]

 

Reported analysis:

92.1% water by weight (pH of juice: 4.6-5) Herrero-Ducloux 1930b

 Mescaline, Anhalamine & Lophophorine

 (all identified by chemical tests)
Mata & McLaughlin 1982 cited Herrero-Ducloux 1930b and Reti 1950 (who also cited Herrero-Ducloux)

 [Ott 1993, page 114, cites Der Marderosian 1966; mentioning this is a simple listing of mescaline species, rather than a primary source.]

 Štarha et al. 1997 did not observe mescaline to be present. See the alkaloid list further below.

Reti 1950 and Chemical Abstracts 1930 says that Enrique Herrero-Ducloux 1930b isolated small amounts of alkaloids from this cactus which he noted gave chemical reactions similar to those of mescaline [Colorless birefringent crystals, n 1.544, mp 160-162°], and what he thought was probably a mixture of anhalonine and lophophorine [Colorless birefringent crystals, n 1.552, mp 188-190°].

No definitive proof was done and apparently only Dr. Štarha has cared enough to follow through during the 70 years which have passed.

 

Gymnocalyciums: Gymnocalycium gibbosum

Gymnocalycium gibbosum

 

External resources:

Cactus-Art

Gymnocalycium.free.fr

 

 

 

 Gymnocalycium leeanum (Hooker) Britton & Rose

William Jackson Hooker (1845) Botanical Magazine; or, Flower-Garden Displayed…, 71: t. 4184, as Echinocactus leeanus
Nathaniel Lord Britton & Joseph Nelson Rose (1922) Cactaceae, 3: 154, fig. 164, as Gymnocalycium leeanum
Wolfgang Papsch (2000) Gymnocalycium, 13 (3): 371. as Gymnocalycium reductum var. leeanum

 

Gymnocalyciums: Gymnocalycium-leeanum-HBG

Gymnocalycium leeanum

Presence of mescaline reported but unconfirmed.

Origin: Argentina and Uruguay

Habitat: Grasslands in rocky places and on hills. Also in organic materials among rocks. Sometimes under shrubs.  IUCN citing Charles 1009.

Echinocactus Leeanus: depresso-globosus obscure subglauco-v i r i d i s tuberculis subhemisphaericis majusculis obtuse hexahedris mammiformibus confluentibus, in series irregulares subverticales dispositis, areolis ovalibus tomentosis, aculeis subgracilibus quorum subdecem patentibus rectiusculis cum unieo centrali porrecta v i x majore, floribus majusculis pallide flavescentibus. (Hooker 1845)

Bluish-green stems ~3 inches thick. Depressed to spherical. [“rather flattened” Innes & Glass]
~16 ribs, irregular, strongly tubercled (more or less six-sided)
Radial spines about 7-10(-11) needle-shaped, thin, appressed, 1/2 inch long.
Central spine 1 straight and directed outward. Not always present.
Flowers pale yellow [“yellowish-white, 2-2½ in long and high” Innes & Glass] to 2 inches (unisexual).
Blooms in early summer.
Backeberg 1959 [3, pages 1735-1737, (includes pictures of two varieties.)
and Backeberg 1977: page 188
and Britton & Rose 1922: page 154 (picture in fig. 164, page 156)
and Hortus Third: page 530.
and Innes & Glass 1991: page 128 (includes picture of species and var. netrelianum, both with flower)

[Schuster 1990 has photo on p. 128.] 

 var. brevispinum Backeberg is described from Maldonado, Uruguay. It is said to have much shorter and straighter spines.

var. netrelianum (Monv.) Backeb, (= G. netrelianum (Monv.) Britt. and Rose Hortus Third Page 530. [see entry of G. netrelium]) Backeberg lists separately; G. leeanum var. netrelianum (Uruguay): tubercle said to be broader than high, spines longer [5-8, centrals absent; Backeberg 1977].

 Innes & Glass describe var. netrelianum as being slightly more globular with fewer, shorter spines (5-7), usually no centrals and having citron yellow flowers 1.5 to 1.75 inches in diameter.

Listed by IUCN as a species of “Least Concern” due to having a fairly wide range that includes protected areas. Its major threats appear to be from human activity and grazing.
Kiesling, R. 2013. Gymnocalycium reductum. The IUCN Red List of Threatened Species. Version 2014.2. www.iucnredlist.org.

Innes & Glass recommend slight shade and a minimum of 50°F.

 

Reported chemistry of Gymnocalycium leeanum:

 Tyramine (gc),

 N-Methyl-tyramine (gc),

 Hordenine (ms, gc),

 Mescaline (chemical tests; unconfirmed),

 Anhalonine (chemical tests)

 and Lophophorine (chemical tests)

     Mata & McLaughlin 1982 citing DeVries et al. 1971 and Herrero-Ducloux 1930b (Apparently DeVries and coworkerrs did not find mescaline, finding the first three phenethylamines instead.
The UT library is missing the first several issues of both journals. It is unknown to me what variety either DeVries or Herrero-Ducloux used or whether this was either noted or even taken into account.)

 

External resources:

Cactus-Art

Gymnocalycium.free.fr

 

 

 

 Gymnocalycium multiflorum (Hooker) Britton & Rose

William Jackson Hooker (1845) Curtis‘ Botanical Magazine, 71: t. 4181, as Echinocactus multiflorus.
Nathaniel Lord Britton & Joseph Nelson Rose (1918) Addisonia, 3: 5, pl. 83, as Gymnocalycium leeanum.
[Now considered lumped as a synonym with Gymnocalycium monvillei
i.e. Nathaniel Lord Britton & Joseph Nelson Rose (1922) Cactaceae, 3: 161, as Gymnocalycium monvillei Pfeiff. ex Britton & Rose.]

 

Gymnocalyciums: Gymnocalycium-multiflorum-flower

Gymnocalycium multiflorum

Gymnocalycium: Gymnocalycium multiflorum Hooker 1845

gymnocalyciums; Gymnocalycium multiflorum Latin diagnosis

 

Herrero-Ducloux 1932a reported recovering small quantities of a ‘mescaline-like’ alkaloid from this species. Reti notes as occuring in Cordoba and Catamarca in Argentina, also in Brazil, Uruguay and Paraguay.
This species is fairly frequent in cactus collections and is readily available commercially. It is one of the more easily
recognizable Gymnocalycium species.

  This report is unconfirmed as it apparently lacks any further work. This species is regarded to be a synonym of Gymnocalycium monvillei which HAS been reported to contain mescaline. See more details under that name.

 

Gymnocalyciums: Gymnocalycium multiflorum

Gymnocalycium multiflorum

 

  G. monvillei is listed as being a species of “Least Concern” by the IUCN.
Demaio, P., Lowry, M., Trevisson, M. & Méndez, E. 2013. Gymnocalycium monvillei. The IUCN Red List of Threatened Species. Version 2014.2. <www.iucnredlist.org>. 

 

External resources:

Gymnocalycium.free.fr

 

 

 Gymnocalycium riograndense Cardeñas

Martin Cárdenas (1958) Kakteen und Andere Sukkulenten, 9: 24, as Gymnocalycium riograndense.
Graham Charles (2005) Cactaceae Systematics Initiatives: Bulletin of the International Cactaceae Systematics Group, 20: 18, as Gymnocalycium pflanzii subsp. zegarrae .

 

Gymnocalyciums: Gymnocalycium-riograndense

Gymnocalycium riograndense

 

Mescaline reported in small amounts.

Origin: Bolivia. Along Rio Grande “between the Cordillera de Cochabamba and the plano of the Rio Guarayos”. Pizzetti 1985.

Habitat: (As G. pflanzi) growing in deep rich soils in sunny rocky areas on slopes or under spiny shrubs. Cactus-Art.

Plants broadly spherical, to 6 cm high, to 20 cm diameter [2-1/2 inches tall and up to 8 inches in diameter]. Initially remaining simple but offshooting from base as adults.
Body is glossy, dark green. [The plant in Pizzeti’s photo is not dark]
Around 13 ribs, to 3 cm wide; Tubercles are obtusely conical, separated by transverse dividing lines; a slender conical beak is below the tubercles.
Round areoles covered with white felt when young but later becoming bare.
8(-9) thin-subulate radial spines, to 2.5 cm long; slightly curving.
They are stiff, grey, black-tipped, brownish below. Later becoming brown all over.
No centrals.
Beaker-shaped flowers are white, with a bluish-red throat.
Backeberg 1977 page 193
and Pizzetti 1985 Entry #126 (Has picture.)

Pizzetti recommends mild winter heat.

 

External resources:

Cactus-Art

Gymnocalycium.free.fr

 

 

 

 Gymnocalycium valnicekianum Jajó

Bedrich Jajó (1934) Kaktusář; odborný měsičnik. Astrophytum spolek pestitelu kaktusu a jinych sukkulentu. Brno, 5: 73. as Gymnocalycium valnicekianum.
Massimo Meregalli & Graham J. Charles (2008) Cactaceae Systematics Initiatives: Bulletin of the International Cactaceae Systematics Group, 24: 25.  as Gymnocalycium mostii subsp. valnicekianum

 

Gymnocalyciums: Gymnocalycium valnicekianum

Gymnocalycium valnicekianum

 

Mescaline reported in small amounts.

Origin: Argentina (Córdoba & El Zapata). (500-)900-1300(-1500)m.

Habitat: Grows among tall grasses in mossy cracks and cavities in rocky cliffs. Cactus-Art.

Broadly spherical at first, later growing spherical to elongated; up to 30 cm high and 18 cm in diameter, sometimes offsetting. Pilbeam notes it to grow larger in cultivation.
Epidermis is smooth and dark grass-green.
Around 10(-13) ribs with swollen, rounded, chin-like tubercles and elliptical areoles with light grey wool.
Spine are variable in number, 7-15 or more. They are whitish-grey to
dirty white, and thickened below. 1-6 central spines. Spines have darker tips at first.”The plants in habitat are each one different from its neighbours! Some had strong spines others weak, curly, straight, long or short ones and in all different combinations” Cactus-Art

Flowers are white with a reddish throat and reddish striped outer petals; 5 cm dia.
Seeds are matt black.
Backeberg 1977 page 195
Pilbeam 1995: 151-152 (Fig. 97)

 Koehres offers var. polycentrale

Schütz also distinguishes var. centrispinum.

 

IUCN lists Gymnocalycium mostii as a species of “Least Concern” due to there being abundance of plants, no significant threats and occurrence in a protected range.
Demaio, P. & Trevisson, M. 2013. Gymnocalycium mostii. The IUCN Red List of Threatened Species. Version 2014.2. <www.iucnredlist.org>. 

 

External resources:

Cactus-Art

Gymnocalycium.free.fr

 

 

 

Gymnocalycium vatteri  Buining

Albert Frederik Hendrik Buining (1950) Succulenta, 66 (1950), as Gymnocalycium vatteri.
Wolfgang Papsch (1993) Gymnocalycium, 6 (1): 79, as Gymnocalycium ochoterenae subsp. vatteri, spelling as ‘ochoterenai‘.
Pilbeam 1995 dismissed the merger by Papsch and a new proposed variety of vatteri, also by Papsch, on the basis of the species known high degree of variability.

 

Gymnocalyciums: Gymnocalycium vatteri

Gymnocalycium vatteri

Mescaline has been reported in small amounts.

Origin: Argentina (Córdoba, Sierra Grande, near Nono). 800-1000m.

Habitat: Amidst rocks and grasses.

Buining 1950 Succulenta, 66, Latin diagnosis of G. vatteri

Buining 1950 Succulenta, 66, Latin diagnosis of G. vatteri

 

Solitary typically but offesetting around the base with age.
Starting flattened hemisperical at first, growing to 4 cm high and 9 cm in diameter.

Epidermis is matt, olive green.
(8-)11(-16), ribs; up to 2.5 cm across and uo to 12 mm high.
Tubercles are swollen and humped, possessing an acute transverse notch beneath.
Areoles are somewhat depressed, ~5 mm wide with grey wool.
3(-5) [1 or 2, sometimes 3 in Pilbeam) Radial spines are appressed or projecting; Pilbeam notes them standing out in youth but curving towards the body with age. They are up to 2 cm and thicker at their base; horn-colored or a dirty darker color.
Spines on the lower part of the plant are variable in both length and curvature but are fairly stout and also sometimes projecting; other spines may be bent and closely appressed.
White flower with a reddish throat in Backeberg and a brownish-grey throat in Pilbeam. 5 cm. long and 4 cm in diameter.
Glossy, light brown seeds; 1 mm in length.
There is a form with more conspicuously claw-like spines but they can also be irregularly interlacing.
Backeberg 1977: page 195 (Fig. 146)
Pilbeam 1995: 152-153 (Fig. 98)

 

Hardy to -5°C. Light shading is recommended. Cactus-Art. Pilbeam describes as slow growing.

 

Gymnocalyciums: Gymnocalycium vatteri

Gymnocalycium vatteri

 

Koehres offers var. cereiformis

 

Gymnocalyciums: Gymnocalycium vatteri

Gymnocalycium vatteri

 

 

External resources:

Cactus-Art

Gymnocalycium.free.fr

 

 

 All of Dr. Štarha’s values for the next section were determined by GC and/or GC-MS. All of the plants that he analyzed were grown from seed in Czechoslovakian greenhouses.

 

Reports of mescaline within the Gymnocalycium species

Synonyms are often mentioned but expect them to keep changing as long as humans keep trying to categorize plants.

Gymnocalyciums: Gymnocalycium achirasense flower

Gymnocalycium achirasense

Gymnocalycium achirasense Till & Schatzl

 Tyramine (0.00159% [± 0.00008])

 N-Methyltyramine (0.00045% [± 0.00006])

 Hordenine (0.00129% [± 0.00006])

 Mescaline (0.00007% [± 0.00001])

 N-Methylmescaline (0.00013% [± 0.00001])

 N,N-Dimethylmescaline (0.00025% [± 0.00002])

 Anhalamine (0.00097% [± 0.00001])

     Štarha et al. 1998 (% by fresh weight)

 [All of Starha’s values in this genus are expressed as % by fresh weight.]

 
Gymnocalyciums: Gymnocalycium-monvillei-Paraguay-6848-EWerdermann-sn-HBG-2006

Gymnocalycium monvillei

 

Gymnocalyciums: Gymnocalycium-asterium-v-paucispinum

Gymnocalycium asterium var. paucispinum

Gymnocalycium asterium Ito

(now merged with Gymnocalycium stellatum)

 Tyramine (0.00089% [± 0.00013])

 N-Methyltyramine (0.00012% [± 0.00004])

 Hordenine (0.00105% [± 0.0001])

 Mescaline (0.00013% [± 0.00002])

 N-Methylmescaline (0.00031% [± 0.00004])

 N,N-Dimethylmescaline (0.0005% [± 0.00004])

 O-Methylanhalidine (0.00011% [± 0.00002])

 Anhalidine (Trace)

 Anhalamine (0.00054% [± 0.00002])

 Anhalonidine (Trace)

 Pellotine (Trace)

 Anhalonine (Trace)

 Lophophorine (Trace)

     Štarha et al. 1998 (% by fresh weight)

Gymnocalyciums: Gymnocalycium-asterium

Gymnocalycium asterium

Compare the analysis of G. asterium to that of G. stellatum.

Gymnocalyciums: Gymnocalycium-baldianum-flowera

Gymnocalycium baldianum

Gymnocalycium baldianum (Spegazzini) Spegazzini

  Tyramine (less than 0.0001%)

  Hordenine (approximately 0.001%)

  Mescaline (less than 0.0001%)

  Anhalinine (less than 0.0001%)

  Anhalidine (less than 0.0001%)

  Anhalamine (less than 0.0001%)

  Anhalonidine (less than 0.0001%)

  Pellotine (less than 0.0001%)

  Anhalonine (less than 0.0001%)

  Lophophorine (less than 0.0001%)

      Štarha 1996

 Reported to contain Betalains as pigments. Wohlpart & Mabry 1968
cited Dreiding 1961

 

Gymnocalyciums: Gymnocalycium calochlorum

Gymnocalycium calochlorum

Gymnocalycium calochlorum (Boedecker) Y.Itô

  Mescaline (between 0.0001-0.001%)

 Tyramine (between 0.0001-0.001%)

  N-Methyltyramine (less than 0.0001%)

  Hordenine (approximately 0.001%)

  N-Methylmescaline (less than 0.0001%)

  Anhalinine (less than 0.0001%)

  Anhalidine (less than 0.0001%)

  Anhalamine (less than 0.0001%)

  Anhalonidine (between 0.0001-0.001%)

  Pellotine (less than 0.0001%)

      Štarha 1996 (% by fresh weight)

Gymnocalyciums: Gymnocalycium calochlorum

Gymnocalycium calochlorum

Gymnocalycium carminanthum Borth & Koop

 Tyramine (0.00007% [± 0.00003])

 N-Methyltyramine (Trace)

 Hordenine (0.00016% [± 0.00005])

 Mescaline (0.00006% [± 0.00005])

 N-Methylmescaline (Trace)

 N,N-Dimethylmescaline (0.00008% [± 0.00002])

 O-Methylanhalidine (0.00007% [± 0.00002])

 Anhalamine (0.00088% [± 0.00003])

 Anhalonidine (Trace)

     Štarha et al. 1998 (% by fresh weight)

 

Gymnocalycium comarapense Backeberg

 Tyramine (Between 0.001-0.001%)

 N-Methyltyramine (Less than 0.001%)

 Hordenine (Less than 0.001%)

 Mescaline (Less than 0.001%)

 N-Methylmescaline (Less than 0.001%)

 Anhalamine (Less than 0.001%)

 Pellotine (Less than 0.001%)

     Štarha 1995 (% by fresh weight)

Gymnocalyciums: Gymnocalycium-denudatum-HBG

Gymnocalycium denudatum

Gymnocalycium denudatum (Link & Otto) Pfeiffer

 Tyramine (0.00066% [± 0.00006])

 N-Methyltyramine (0.00061% [± 0.00002])

 Hordenine (0.00052% [± 0.00005])

 Mescaline (Trace)

 N-Methylmescaline (0.00008% [± 0.00001])

 N,N-Dimethylmescaline (0.00073% [± 0.00005])

 O-Methylanhalidine (0.00025% [± 0.00003])

 Anhalinine (0.00006% [± 0.00002])

 O-Methylanhalonidine (0.0001% [± 0.00002])

 Anhalidine (Trace)

 Anhalamine (0.00048% [± 0.00002])

 Anhalonidine (Trace)

     Štarha et al. 1998 (% by fresh weight)

Gymnocalyciums: Gymnocalycium fleisheranum

Gymnocalycium fleisheranum

Gymnocalycium fleischerianum Backeberg

(Now considered

  Tyramine (0.0001-0.001% dry wt.)

  N-Methyltyramine (0.001% dry wt.)

  Hordenine (0.0001-0.001% dry wt.)

  Mescaline (0.0001-0.001% dry wt.)

  N-Methylmescaline (0.0001-0.001% dry wt.)

  N,N-Dimethylmescaline (0.0001-0.001% dry wt.)

  Anhalamine (0.0001-0.001% dry wt.)

  Anhalonidine (0.00001-0.0001% dry wt.)

    Štarha 2001c did not include a citation for this information. (G. fleischerianum is included only in his table on page 91 and not in the by species breakdown)

Gymnocalyciums: Gymnocalycium fleisheranum

Gymnocalycium fleisheranum

 

Gymnocalyciums: Gymnocalycium gibbosum

Gymnocalycium gibbosum

Gymnocalycium gibbosum (Haworth) Pfeiffer

 92.1% water by weight (pH of juice: 4.6-5.0) Herrero-Ducloux 1930b

  Tyramine (Less than 0.0001%) Štarha et al. 1997

  N-Methyltyramine (approximately 0.001%) Štarha et al. 1997

  Hordenine (approximately 0.001%) Štarha et al. 1997

  Mescaline (unquantified and tentatively identified. Colorless birefringent crystals, n 1.544, mp 160-162o were claimed to show the “reactions of mescaline”) Herrero-Ducloux 1930b. Mescaline was NOT observed by Štarha
et al. 1997.

 N-Methylmescaline (Between 0.0001-0.001%) Štarha et al. 1997

  N,N-Dimethylmescaline (Less than 0.0001%) Štarha et al. 1997

  O-Methylanhalidine (approximately 0.001%) Štarha et al. 1997

  Anhalinine (approximately 0.001%) Štarha et al. 1997

  O-Methylanhalonidine (approximately 0.001%) Štarha et al. 1997

  Anhalidine (Between 0.0001-0.001%) Štarha et al. 1997

  Anhalamine No quantification (or accurate identification) attempted; Herrero-Ducloux 1930b [Our source was Reti; CA gives this as Anhalonine. I presently lack the primary paper.] (approximately 0.001%) Štarha et al. 1997

  Anhalonidine (Less than 0.0001%) Štarha et al. 1997

  Pellotine (Between 0.0001-0.001%) Štarha et al. 1997

  Anhalonine (Between 0.0001-0.001%) Štarha et al. 1997

  Lophophorine No quantification (or accurate identification) attempted; Herrero-Ducloux 1930b. Between 0.0001-0.001%: Štarha et al. 1997

 Gymnocalycium horridispinum Frank

  Mescaline (between 0.0001-0.001%)

  Tyramine (approximately 0.001%)

  N-Methyltyramine (less than 0.0001%)

  Hordenine (approximately 0.001%)

  N-Methylmescaline (less than 0.0001%)

  Anhalinine (less than 0.0001%)

  Pellotine (less than 0.0001%)

      Štarha 1996 (% by fresh weight)

Gymnocalyciums: Gymnocalycium leeanum

Gymnocalycium leeanum

Gymnocalycium leeanum (Hooker) Br. & R.

[Now considered

  Anhalonine (Unconfirmed) Herrero-Ducloux 1930b

 Not observed by DeVries et al. 1971

  Hordenine (%?) DeVries et al. 1971

  Lophophorine (Unconfirmed) Herrero-Ducloux 1930b

 Not observed by DeVries et al. 1971

  Mescaline (Unconfirmed) Herrero-Ducloux 1930b

 Not observed by DeVries et al. 1971

  N-Methyltyramine  (?%) DeVries et al. 1971

  Tyramine (0.00583%) DeVries et al. 1971

Gymnocalyciums: Gymnocalycium leeanum

Gymnocalycium leeanum

 

 

Gymnocalyciums: Gymnocalycium-mesopotamicum-HBG

Gymnocalycium mesopotamicum

 Gymnocalycium mesopotamicum Kiessling

 Tyramine (Trace)

 N-Methyltyramine (Trace)

 Hordenine (Trace)

 Mescaline (Trace)

 N-Methylmescaline (Trace)

 N,N-Dimethylmescaline (0.00279% [± 0.0005])

 Anhalamine (0.0019% [± 0.00028])

 Anhalonidine (0.00005% [± 0.00003])

     Štarha et al. 1998 (% by fresh weight)

Gymnocalyciums: Gymnocalycium-monvillei-Paraguay-6848-EWerdermann-sn-HBG-2006

Gymnocalycium monvillei

 Gymnocalycium monvillei (Lemaire) Britton & Rose

 Tyramine (Between 0.0001-0.001%)

 N-Methyltyramine (Between 0.0001-0.001%)

 Hordenine (Approximately 0.001%)

 Mescaline (Less than 0.0001%)

 N-Methylmescaline (Less than 0.0001%)

 N,N-Dimethylmescaline (Less than 0.0001%)

 O-Methylanhalidine (Less than 0.0001%)

 Anhalinine (Less than 0.0001%)

 O-Methylanhalonidine (Less than 0.0001%)

 Anhalidine (Less than 0.0001%)

 Anhalamine (Less than 0.0001%)

 Anhalonidine (Between 0.0001-0.001%)

 Pellotine (Between 0.0001-0.001%)

 Anhalonine (Between 0.0001-0.001%)

 Lophophorine (Less than 0.0001%)

     Štarha et al. 1997 (% by fresh weight)

 

Gymnocalycium moserianum Schutz

 Tyramine (0.00077% [± 0.0001])

 N-Methyltyramine (0.0001% [± 0.00003])

 Hordenine (0.00011% [± 0.00003])

 Mescaline (0.00007% [± 0.00001])

 N-Methylmescaline (0.00151% [± 0.00015])

 N,N-Dimethylmescaline (0.00071% [± 0.00006])

 O-Methylanhalidine (0.00007% [± 0.00001])

 Anhalinine (0.00007% [± 0.00001])

 O-Methylanhalonidine (0.00007% [± 0.00001])

 Anhalidine (0.00007% [± 0.00001])

 Anhalamine (0.00215% [± 0.00014])

 Anhalonidine (0.00014% [± 0.00003])

 Pellotine (0.00012% [± 0.00003])

 Anhalonine (Trace)

 Lophophorine (Trace)

     Štarha et al. 1998 (% by fresh weight)

Gymnocalyciums: Gymnocalycium multiflorum

Gymnocalycium multiflorum

Gymnocalycium multiflorum

(Now considered to be at least partially a synonym with Gymnocalycium monvillei.)

Herrero-Ducloux 1932a reported recovering small quantities of a ‘mescaline-like’ alkaloid from this species.

This report for this cactus species presently lacks confirmation.

 

 Gymnocalycium netrelianum Britton & Rose

 Tyramine (Less than 0.001%)

 Hordenine (Between 0.0001-0.001%)

 Mescaline (Between 0.0001-0.001%)

 N-Methylmescaline (Less than 0.001%)

 Pellotine (Less than 0.001%)

     Štarha 1995a (% by fresh weight)

Gymnocalycium nigriareolatum Backeberg

 Tyramine (0.00047% [± 0.00005])

 N-Methyltyramine (0.00008% [± 0.00002])

 Hordenine (0.0014% [± 0.00006])

 Mescaline (0.00006% [± 0.00002])

 N-Methylmescaline (0.00006% [± 0.00001])

 N,N-Dimethylmescaline (0.00009% [± 0.00002])

 O-Methylanhalidine (0.00012% [± 0.00006])

 Anhalamine (0.00019% [± 0.00004])

 Anhalonidine (0.00008% [± 0.00002])

     Štarha et al. 1998 (% by fresh weight)

Gymnocalyciums: Gymnocalycium-oenanthemum

Gymnocalycium oenanthemum

Gymnocalycium oenanthemum Backeberg

 Tyramine (Between 0.0001-0.001%)

 N-Methyltyramine (Less than 0.0001%)

 Hordenine (approximately 0.001%)

 Mescaline (Less than 0.0001%)

 N-Methylmescaline (Less than 0.0001%)

 N,N-Dimethylmescaline (Less than 0.0001%)

 O-Methylanhalidine (Less than 0.0001%)

 O-Methylanhalonidine (Less than 0.0001%)

 Anhalidine (Less than 0.0001%)

 Anhalamine (Less than 0.0001%)

 Anhalonidine (Between 0.0001-0.001%)

 Pellotine (Between 0.0001-0.001%)

 Anhalonine (Less than 0.0001%)

 Lophophorine (Less than 0.0001%)

      Štarha et al. 1997 (% by fresh weight)

Gymnocalycium paraguayense Schutz

 Tyramine (0.00047% [± 0.00004])

 N-Methyltyramine (0.00104% [± 0.00014])

 Hordenine (0.00043% [± 0.00008])

 Mescaline (0.00011% [± 0.00006])

 N-Methylmescaline (0.00041% [± 0.0001])

 N,N-Dimethylmescaline (0.00427% [± 0.00032])

 Anhalamine (0.00505% [± 0.0005])

 Anhalonidine (0.00017% [± 0.00006])

     Štarha et al. 1998 (% by fresh weight)

Gymnocalyciums: Gymnocalycium-quehlianum

Gymnocalycium quehlianum

Gymnocalycium quehlianum (Haage) Berg.

  Tyramine (Between 0.0001-0.001%)

  N-Methyltyramine (Between 0.0001-0.001%)

  Hordenine (approximately 0.001%)

  Mescaline (Less than 0.0001%)

  N-Methylmescaline (Less than 0.0001%)

  N,N-Dimethylmescaline (Less than 0.0001%)

  Anhalinine (Less than 0.0001%)

  O-Methylanhalonidine (Between 0.0001-0.001%)

  Anhalonidine (Less than 0.0001%)

  Pellotine (Less than 0.0001%)

  Anhalonine (Less than 0.0001%)

  Lophophorine (Less than 0.0001%)

      Štarha et al. 1997 (% by fresh weight)

 Gymnocalycium ragonesii Cast.

 Tyramine (0.00009% [± 0.00002])

 N-Methyltyramine (0.00005% [± 0.00001])

 Hordenine (0.0035% [± 0.00014])

 Mescaline (Trace)

 N-Methylmescaline (Trace)

 N,N-Dimethylmescaline (Trace)

 O-Methylanhalidine (0.00048% [± 0.00003])

 Anhalinine (0.00109% [± 0.00018])

 O-Methylanhalonidine (0.00007% [± 0.00001])

 Anhalidine (0.00006% [± 0.00001])

 Anhalonidine (Trace)

 Pellotine (Trace)

     Štarha et al. 1998 (% by fresh weight)

Gymnocalyciums: Gymnocalycium riograndense

Gymnocalycium riograndense Cardeñas

(Now Gymnocalycium pflanzii subsp. zegarrae)

Tyramine (Between 0.0001-0.001%)

 N-Methyltyramine (Less than 0.001%)

 Hordenine (Less than 0.001%)

 Mescaline (Between 0.0001-0.001%)

 N-Methylmescaline (Less than 0.001%)

 Anhalinine (Less than 0.001%)

 Anhalidine (Less than 0.001%)

 Anhalonidine (Less than 0.001%)

 Pellotine (Less than 0.001%)

 Anhalonine (Less than 0.001%)

 Lophophorine (Less than 0.001%)

     Štarha 1995a (% by fresh weight)

Gymnocalycium riojense Fric ex H.Till & W.Till

  Tyramine (0.001% dry wt.)

  N-Methyltyramine (0.00001-0.0001% dry wt.)

  Hordenine (0.001% dry wt.)

  Mescaline (0.00001-0.0001% dry wt.)

  N-Methylmescaline (0.00001-0.0001% dry wt.)

  Anhalinine (0.00001-0.0001% dry wt.)

  O-Methylanhalonidine (0.00001-0.0001% dry wt.)

  Pellotine (0.00001-0.0001% dry wt.)

  Anhalonidine (0.00001-0.0001% dry wt.)

     Štarha 2001c cited Štarha 2001a

Gymnocalyciums: Gymnocalycium-stellatum-HBG

Gymnocalycium stellatum

Gymnocalycium stellatum Spegazzini

  Tyramine (Between 0.0001-0.001%)

  N-Methyltyramine (Less than 0.0001%)

  Hordenine (approximately 0.001%)

  Mescaline (Less than 0.0001%)

  N-Methylmescaline (Between 0.0001-0.001%)

  N,N-Dimethylmescaline (Less than 0.0001%)

  Anhalinine (Between 0.0001-0.001%)

  O-Methylanhalonidine (Less than 0.0001%)

  Anhalamine (Less than 0.0001%)

  Anhalonidine (Between 0.0001-0.001%)

  Pellotine (Between 0.0001-0.001%)

  Anhalonine (Between 0.0001-0.001%)

  Lophophorine (Less than 0.0001%)

      Štarha et al. 1997 (% by fresh weight)

Gymnocalycium striglianum Jeggle

  Tyramine (Less than 0.001%)

 Hordenine (Less than 0.001%)

 Mescaline ( “readily apparent” at around 0.001%)

 N-Methylmescaline ( “readily apparent” at around 0.001%)

 Anhalinine (Less than 0.001%)

 Anhalidine (Less than 0.001%)

 Anhalamine ( “readily apparent” at around 0.001%)

 Anhalonidine (Less than 0.001%)

 Pellotine ( “readily apparent” at around 0.001%)

 Anhalonine (Less than 0.001%)

 Lophophorine (Less than 0.001%)

     Štarha 1995a (% by fresh weight)

Gymnocalyciums: Gymnocalycium triacanthum

Gymnocalycium triacanthum

Gymnocalycium triacanthum Backeberg

 Tyramine (Trace)

 N-Methyltyramine (0.00005% [± 0.00001])

 Hordenine (0.00054% [± 0.00004])

 Mescaline (Trace)

 N-Methylmescaline (Trace)

 N,N-Dimethylmescaline (Trace)

 O-Methylanhalidine (0.00015% [± 0.00001])

 Anhalinine (0.00014% [± 0.00001])

 Anhalidine (Trace)

 Anhalonidine (0.0006% [± 0.00001])

     Štarha et al. 1998 (% by fresh weight)

Gymnocalyciums: Gymnocalycium triacanthum

Gymnocalycium triacanthum

Gymnocalycium uebelmannianum Rausch

  Tyramine (Between 0.0001-0.001%)

  N-Methyltyramine (Between 0.0001-0.001%)

  Hordenine (Between 0.0001-0.001%)

  Mescaline (Between 0.0001-0.001%)

  N-Methylmescaline (Less than 0.0001%)

  N,N-Dimethylmescaline (Less than 0.0001%)

  O-Methylanhalidine (Less than 0.0001%)

  Anhalinine (Between 0.0001-0.001%)

  O-Methylanhalonidine (Between 0.0001-0.001%)

  Anhalidine (Less than 0.0001%)

  Anhalamine (Between 0.0001-0.001%)

  Anhalonidine (Between 0.0001-0.001%)

  Pellotine (Between 0.0001-0.001%)

  Anhalonine (Less than 0.0001%)

  Lophophorine (Less than 0.0001%)

      Štarha et al. 1997 (% by fresh weight)

Gymnocalyciums: Gymnocalycium valnicekianum

Gymnocalycium valnicekianum seedling

Gymnocalycium valnicekianum Jajó

(now Gymnocalycium mostii subsp. valnicekianum)

 Tyramine (Between 0.0001-0.001%)

 N-Methyltyramine (Less than 0.001%)

 Hordenine ( “readily apparent” at around 0.001%)

 Mescaline (Less than 0.001%)

 Anhalinine (Less than 0.001%)

 Anhalonidine (Between 0.0001-0.001%)

 Pellotine (Less than 0.001%)

 Anhalonine (Less than 0.001%)

 Lophophorine (Less than 0.001%)

     Štarha 1995a (% by fresh weight)

Gymnocalyciums: Gymnocalycium vatteri

Gymnocalycium vatteri

 Gymnocalycium vatteri Buining

(now Gymnocalycium ochoterenae subsp. vatteri, or not; depending upon with whom you want to agree.)

  Mescaline (between 0.0001-0.001%)

  Tyramine (approximately 0.001%)

  N-Methyltyramine (between 0.0001-0.001%)

  Hordenine (approximately 0.001%)

  N-Methylmescaline (between 0.0001-0.001%)

  Anhalinine (approximately 0.001%)

  Anhalidine (less than 0.0001%)

  Anhalonidine (between 0.0001-0.001%)

  Pellotine (between 0.0001-0.001%)

  Anhalonine (less than 0.0001%)

  Lophophorine (less than 0.0001%)

      Štarha 1996 (% by fresh weight)

Gymnocalyciums: Gymnocalycium vatteri

Gymnocalycium vatteri

 

 

 Parting comment on the genus Gymnocalycium and South American globulars:

 It is puzzling that this large genus and area has been neglected for so many years, in light of the intense academic interest which has intermittently surrounding such plants.The work of Dr. Štarha underscores the need for more in depth work. While the reported concentrations overall are low, this is in line with the majority of cacti tested; the high mescaline producers are only sporadically represented and apparently difficult to predict.  Štarha’s results are encouraging despite low values.

 Considering how many different Gymnocalycium species are readily available, how easy they are to grow, how often this is mentioned in the literature and how many of the larger flat species actually resemble Peyote in color and appearance, it is mind boggling that more people have not pursued further chemical work in this fascinating and attractive group.

 G. platense and G. riograndensis have long been suggested as probable mescaline containing species but, as far as it can be determined, this was implied solely by morphology as no actual chemical work had been done. More recently, Dr. Štarha did indeed find small amounts of mescaline in the latter.

 An interesting mention is made of globular cacti in Margaret Ashley Towle 1961. Her reference, Eugenio Yácovleff & Fortunato L. Herrera 1934, mention Lobivia (L. corbula), Mammillaria (M. herrerae) (equating these first two) and Melocacti in passing, during their discussion of the many varied forms of cacti found depicted in ceramic designs. (pages 319-320, ceramic design examples also on page 321). [Their reference to Melocacti was in regards to the Peruvian species which form distinct Cereus-like columns somewhat resembling Neoraimondia and Armatocereus species but it should be mentioned that most Melocacti exist as fairly globular plants.]

 Some types of globular cacti are clearly depicted. While mescaline has not yet been reported from these plants, many Lobivia, Mammillaria, Melocacti, and Echinopsis species, as well as additional non-mescaline containing Gymnocalyciums, have all been reported to contain alkaloids.

 I would suggest more representative species be examined for all.

Azketium ritteri

Aztekium ritteri (Bödeker) Bödeker

Friedrich Boedeker  (1929) Monatsschrift für Kakteenkunde, 1: 52. Aztekium ritteri
Friedrich Boedeker  (1928) Zeitschrift für Sukkulentenkunde. Berlin 3 (14): 305–306. Echinocactus ritterii


Aztekium ritteri

 

Small amounts of mescaline have been reported. 

Etymology: The wonderful texture of its surface has been likened to some Aztec motifs, hence the genus name Aztekium. Friedrich Ritter (who had been living in Mexico) was the specific namesake.

Habitat: From Nuevo Leon, Mexico growing in xeric scrub on limestone and gypsum cliffs.

Often remains solitary but may be freely offsetting from base with age (or if grafted or after exposure to pesticides & fungicides). 
Greyish-green to grey body is broad and rounded to around 2 inches in
diameter; with a depressed wooly top.

Short napiform taproot.
9-11 ribs, [Ed.: Sometimes swirling] folded, with subsidiary and narrower ribs in between.] 
Cultivated plants tend to be more green. Especially so on grafted plants. This is considered a detractant to the beauty of this plant by most authorities and serious collectors.
Areoles are closely set and bear white hairs.
Few spines; weak, bent or contorted. Usually 1-3; 3-4 mm in length.
White flowers 8 mm in diameter, appearing to have a stalk.
[Pizetti describes flowers as being about 1 cm wide; with white segments and outer perianth parts with pink edges. Anderson 1998 describes the flowers as white to light pink and appearing sporadically throughout the summer.]
Pink fruit is berrylike and appears only when ripe.
Black seeds are 0.5 mm long.
    Backeberg 1977: 79-80 and
    Pizetti 1985 entry #15.

Backeberg noted that there is also a form with flower that is longer (has longer stalk)

See also Backeberg 1961 [5: 2890-2892], (includes pictures on page 2891, fig. 2722, and the larger flowered form in flower, fig. 2723.) and Lamb & Lamb 1971 [2: 378] (with picture). Pizetti has color picture.

Habitat photos: Chastek 1994 Kaktusy 2: 40-41

Backeberg & Pizetti (& many others) describe the species as cold sensitive but I have seen them tolerate hard freezes (6°F) in a covered but unheated outdoor cactus bed Austin Texas when totally dry. I would recommend protection from freezing despite that lucky experience.

Once considered an endangered species due to being found only in a restricted area experiencing heavy collection activity. More populations across a broad range have since been discovered. The habitat includes inaccessible populations due to restricted access for both humans and browsers so it has been downgraded to become listed as a species of “Least Concern“.
      B. Fitz Maurice & W.A. Fitz Maurice 2013. Aztekium ritteri. The IUCN Red List of Threatened Species. Version 2014.2. www.iucnredlist.org.

Reported analysis:
(Plants greenhouse grown in Czechoslovakia)
N-Methyltyramine (0.0031% by fresh wt.)
3-Methoxytyramine (Less than 0.0001% by fresh wt.)
Hordenine (Less than 0.0001% by fresh wt.)
N,N-Dimethyl-3,4-dimethoxyphenethylamine (0.0036% fresh wt.)
Mescaline (0.0009% by fresh wt.) (Which is not quite a mg per kg.)
Anhalidine (0.0008% by fresh wt.)
Pellotine (0.0026% by fresh wt.)
    Štarha 1994

[Aztekium ritteri has had an unconfirmed claim of caffeine. No reference was cited and none has been located. Claims for caffeine have never been sustantiated in any cactus species.]

Glucaric acid (tlc by Kringstad & Nordal 1975)
Quinic acid (tlc, glc & gc-ms by Kringstad & Nordal 1975)

 

 

Alwin Berger 1929 Kakteen, pp. 259-260.

Aztekium ritteri description

 

External links:

Dave’s Garden’s

IPNI

ThePlantList

Tropicos

Garden of Eden

   Garden of Eden is an amazing work by my friend Snu Voogelbreinder.

 

GOE_01

   Snu Voogelbreinder has at-long-last released a PDF of his magnum opus. Anyone who missed out on acquiring a copy of his book now has another opportunity! I am posting a link below for convenience.

   “Garden of Eden (2009 1st edition) is now available as a pdf, for the modest price of AU$12 (Australian dollars).
Please follow the link below to purchase and download the book.”

   Payment is through PayPal which accepts payment in almost any currency.


  All payments are via PayPal but you can use a credit card
and you do not need to have or to create a PayPal account.

Either of the links above will take you to a secure PayPal page.
”    Some glitches have been reported lately with the purchase link – please try again later if it does not work the first time, as this usually resolves the issue. Thanks for your patience.”

Another comment from Snu:
   “Here is a free download of Errata for Garden of Eden (1st edition), listing and correcting a few things that eluded me before publishing. Thanks to Keeper Trout for bringing some of these to my attention!”

   Garden of Eden, by Snu Voogelbreinder explores the vast world of psychoactive plants, animals and other organisms, and their uses in shamanism, spiritual exploration and healing. Encompassing scientific research, personal experience, ancient knowledge and esoteric philosophies, a multidisciplinary approach is taken, giving a wide view of the effects of natural substances on the mind, with an emphasis towards beneficial outcomes. Preliminary information is given regarding neurochemistry, drug-free consciousness alteration, and methods of use, from cultivation or wild-sourcing through to harvesting, processing, consumption and navigation of the effects. Thousands of species from over 1700 genera are discussed, with over 440 genera covered in greater detail, including botanical and zoological descriptions. Also included are a detailed index of natural chemicals of particular interest, and a huge bibliography containing thousands of reference entries.

   The book is partly illustrated in black & white, 510 pages, hardcover (22cm x 30.7cm x 4.1cm). Printed on sturdy Envirocare 100% Recycled post-consumer fibre (chlorine-free), using vegetable oil-based inks, benign press chemicals and 100% solar power in pre-press and print production. The manufacture was carbon-neutral.

   This edition was self-published by the author and limited to 500 copies.

To contact the author, send an e-mail message to:

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   Garden Of Eden is now sold out! Snu would like to thank all those people who now own a copy for their patronage (which has benefited several charities) and extended words of appreciation. Their support helped make it all worthwhile.

   This book is a fine complement to other classics of the genre, such as Christian Rätsch’s Encyclopedia of Psychoactive Plants, Jonathan Ott’s Pharmacotheon and Trout’s Notes.

 

GOE_2

Abbreviations used in Sacred Cacti

Areole of Trichocereus pachanot compared to Trichocereus scopulicola

 

A simple listing of the technical abbreviations used in the 4th edition

µm = micrometer = micron

ml = milliliter

Å = angstrom

MLD = minimum lethal dose reported in literature

BCE = before current era

mM = milliMolar

BP = before present

mm = millimeter

bp= boiling point

mmp = mixed melting point

cm = centimeter

mp = melting point

dec. = with decomposition

ms = mass spectroscopy

dm = decimeter (10 cm.)

na = not available/applicable

et al. = et alia (“& others”)

nd = not detected

f = forma

nm = nanometer

ft = foot

nn = nomen nudum (named but lacking any description)

gc = gas chromatography

RT = room temperature

gm = gram

sc = subcutaneous

in = inch

sn = sine numero(lacking a collection number)

im = intramuscular

sp = species (singular)

ip = intraperitoneal

spp = species (plural)

ir = infrared

ssp = subspecies

iv = intravenous

subsp = subspecies

kg = kilogram

TD = toxic dose

kV = kilovolt

TLC = thin-layer chromatography

LD100 = lethal dose 100%

uv = ultraviolet

LD50 = lethal dose 50%

v = volt

mm = millimicron (= nm)

var = variety

m = meter

X = indicates a hybrid

ma = milliamp

MAO = monoamine oxidase

MAOI = mao inhibitor

 

 

Chapter 3; distribution & occurrences

Trichocereus peruvianus P.C.Hutchison 543. (Found at 1700m)
Collected in the canyon of the Río Rímac, Huarochiri Prov., Peru

 

 

The Distribution & Occurrence of Mescaline


This chapter is intended as an overview to set the stage for the next chapter detailing the mescaline containing species. In the work which follows, most taxonomic synonyms were omitted as these are readily available in the sources cited and are primarily only of historical importance. (More detailed and ‘properly’ worded taxonomic descriptions of the plants can be found in the listed references.)

        To better assist the reader in search of more information it was thought helpful to include synonyms that are in horticultural use or used in the references included.

        Many times plants get renamed or transferred by one authority without being accepted by some or most others. In some cases, such as Stenocereus, it is not uncommon to find several different names for the same plant depending on which reference work one consults. While it is unlikely that they would be encountered and still referred to as a Cereus, as many cereoids were originally called, it is just as likely they will not be listed by MOST sources as a Stenocereus.

        Any feedback on how this could be made more useful and accessible is welcomed.

Proviso:

        It must be kept in mind that substantial differences in the alkaloid content and in the relative ratios of alkaloids present have been noted by numerous researchers. (True also in many other families.) These differences have been noted to sometimes appear seasonally, such as the higher presence of N-methylated (as compared to N-demethylated) alkaloids detected, by Lundstrom, during summer in greenhouse maintained peyote. In contrast; in the same population of plants, winter analysis found levels of N-demethylated compounds to be higher than N-methylated ones. [While he used cultivated plants, the mescaline content was comparable to most of what is collected from the wild.]

        They can vary as well according to the age of plant (young plant versus adult plant) or even by age of part (such as new growth on a large adult compared to older growth). In cacti, the actual variables effecting such reports are, usually, unknown and unstudied.

        Alkaloid content has been noticed to vary substantially in amount and/or actual even composition between varieties considered closely related by morphology, and concentrations sometimes vary widely even from one individual or locality to the next. In others even daily fluctuations have been noted; in Phalaris and Papaver, for example, alkaloid concentrations were found to be highest in the early morning. (Quantitative comparative isolations of Phalaris was reported by Appleseed.)

        Very few workers seem to concern themselves with any of this and rigorous work on this subject has rarely been performed or published.
The bottom line is that a published analysis says something about the actual material analyzed by those particular workers and can be reliably extrapolated to mean almost nothing concerning what YOU have or another person possesses. It CAN be valuable as an indication of what molecules might be anticipated but the composition and quantification of alkaloids needs to be determined on YOUR plants in order to know what you actually have. Plants do not read, listen to or follow the publications of scientists.

        [Species suggested by published analysis to be variously weak or potent have on occasion proved to be just the opposite!]

        Often the only data included is whether the plant was cultivated or collected from the wild. In many early papers we literally have to rely on the word of the workers as to the identity of what they analyzed, as vouchers for reference’s sake were never prepared and there is no physical means for confirmation.

        Fortunately, in recent decades, far more attention is being given to the importance of proper herbarium vouchers being prepared for any and all plant analysis. Even in these cases, not all workers note enough variables for their observations to be truly meaningful.

         Critical data for wild plant collections: size and approximate age, part of plant used and stage of growth, i.e. actively growing versus fully developed (if sampling only branches of large specimens), and time of harvest (time of year and time of day) should all be included along with place of origin and elevation of occurrence.

         Ideally for a voucher some comments on the local ecology and a description of habitat would also be quite valuable. This could include the plants growing around it, or with it, the immediate local conditions of occurrence [moisture, degree of sun, etc…], its apparent niche in ecosystem, and a description of the land or terrain.

         Even better would be additionally including a local soil test and/or sample, and analyzing as many parts and ages of material as possible, as well as repeated tests with the same specimens at different times of year.

         If performing repeated samplings of the same individuals; stress can become a factor capable of influencing the results. I suggest initially using pooled smaller samples of adjacent individuals within a given population. There should be additional small samples taken from several individuals within the same population that is pooled in order to check for uniformity and evaluate the degree of potential influence from outliers.

         Most plants can recover rapidly and well from light prunings. A minimum of two years time is suggested for such a series of samplings with a maximum of 6-8 trimmings. Differences in regrowth versus original growth should also be evaluated.

         The factors controlling and regulating alkaloid production would be a fascinating and productive area for future academic research. If chemotaxonomy is to ever be considered a truly useful inclusion in the repertoire of taxonomic tools, science needs to be better able to define the parameters of alkaloid production.

         Determining and taking steps to maximize alkaloid content would also be of benefit for those who view these plants as sacraments. Selection for known high alkaloid strains, or focusing on clones of specific exceptional individuals, for intensive large scale breeding and propagation efforts, would be a worthwhile avenue for everyone involved with sacramental use of these plants.

 

distribution; Opuntia-ficus-indica

a thirsty Opuntia ficus-indica growing in Australia

 

The distribution of mescaline containing species within the Cactaceae

Nonbold face specific names indicate acceptance as a species is still not widely recognized.

Family: Cactaceae

     Subfamily: Cereoideae

        Tribe Pereskieae

Pereskia corrugata 

Pereskia tampicana

          Tribe Opuntieae

Pereskiopsis scandens 

              subtribe Cylindropuntia 

Opuntia acanthocarpa 

Opuntia echinocarpa 

Opuntia imbricata 

Opuntia spinosior 

subtribe Opuntia 

Opuntia basilaris 

Opuntia ficus-indica

          Tribe Cacteae

            subtribe Cactinae 

Pelecyphora aselliformis 

            subtribe Cereinae 

Polaskia chende 

Pterocereus gaumeri 

Stenocereus beneckei 

Stenocereus eruca 

Stenocereus stellatus 

Stenocereus treleasei 

Stetsonia coryne 

Trichocereus bridgesii ***(all forms*)

Trichocereus bridgesii monstrosus *** 

Trichocereus cuzcoensis *** [Often 0.0%. See its entry.]

Trichocereus fulvilanus 

Trichocereus huanucoensis

Trichocereus macrogonus *** 

Trichocereus pachanoi *** 

Trichocereus pachanoi monstrosus

Trichocereus pallarensis *** 

Trichocereus peruvianus *** 

Trichocereus peruvianus monstrosus

Trichocereus puquiensis *** 

Trichocereus puquiensis monstrosus

Trichocereus santaensis *** 

Trichocereus schoenii *** 

Trichocereus scopulicola *** 

Trichocereus sp. W.Baker 5452 ** 

Trichocereus cv. SS01, SS02, SS03

Trichocereus cv. TJG *** 

Trichocereus sp. Torres & Torres: N. Chile

Trichocereus cv. “Unknown C”

Trichocereus sp. aff. huanucoensis

Trichocereus strigosus 

Trichocereus taquimbalensis

Trichocereus terscheckii *** 

Trichocereus thelegonoides 

Trichocereus uyupampensis *** (Erroneous ID)

Trichocereus validus 

Trichocereus vollianus 

Trichocereus werdermannianus *** 

            subtribe Echinocactinae 

Aztekium ritteri 

Gymnocalycium achirasense 

Gymnocalycium asterium 

Gymnocalycium baldianum 

Gymnocalycium calochlorum 

Gymnocalycium carminanthum 

Gymnocalycium comarapense 

Gymnocalycium denudatum 

Gymnocalycium gibbosum 

Gymnocalycium horridispinum 

Gymnocalycium leeanum 

Gymnocalycium mesopotamicum 

Gymnocalycium monvillei 

Gymnocalycium moserianum 

Gymnocalycium netrelianum 

Gymnocalycium nigriareolatum 

Gymnocalycium oenanthemum 

Gymnocalycium paraguayense 

Gymnocalycium quehlianum 

Gymnocalycium ragonesii 

Gymnocalycium riograndense 

Gymnocalycium stellatum 

Gymnocalycium striglianum 

Gymnocalycium triacanthum 

Gymnocalycium uebelmannianum 

Gymnocalycium valnicekianum 

Gymnocalycium vatteri 

Islaya minor 

Lophophora diffusa *** (but not usual case)

Lophophora fricii *** [Does not appear to be typical. May have been an ID error?]

Lophophora jourdaniana *** 

Lophophora koehresii 

Lophophora williamsii williamsii *** 

Lophophora williamsii echinata *** 

Turbinicarpus lophophoroides 

Turbinicarpus pseudomacrochele var. krainzianus 

Turbinicarpus schmiedickianus var. flaviflorus 

Turbinicarpus schmiedickianus var. schwarzii 

 


Please note that this system of organization is presently no longer accepted by most authorities but it is still commonly encountered in horticulture and among ethnobotanists.

        However, an attempt was made by Albesiano & Kiesling in 2011 to resurrect the genus Trichocereus and all of the molecular work to-date indicates that they are on solid ground. See elsewhere in this work for more details.

        Most of the species listed contain only trace amounts.

        Species marked * lack formally published analytical work but have successful human bioassays reported.

        Species marked ** have unpublished analytical work confirming mescaline’s presence as well as successful human bioassays reported.

        Species marked *** have both published analytical work & successful human bioassays reported.

 

distribution; Acharagma-aguirreana

Acharagma aguirreana (Glass & R.Foster) Glass
(Formerly known as Gymnocactus aguirreanus Glass & R.Foster.)
DNA work by Wallace suggests that this may be Lophophora diffusa’s closest relative.
Reported to contain over 2% hordenine by West et al. 1974.


A more recent view

        This is that same list but using the currently accepted names. Species that are missing from this list were variously discarded, merged or ignored in the revisions. Details can be found under their entries.

        One thing that careful readers will notice about this arrangement is that some of the new combinations merge plants with quite different published chemistry. If a plant reported to contain mescaline was renamed as a synonym of one which did not it was omitted from this list.

        I would suggest that these be looked at closer with an eye for possible subdivision into chemical races.

        Comparisons of Anderson, Hunt & others will also rapidly reveal a lack of agreement on a number of points and the seemingly capricious acceptance of some and rejection of others with little if any comment. Hunt’s lack of meaningful references, including in some cases the actual describers, precludes any resolution in a number of instances.

        Some of the combinations are so peculiar as to have caused me to wonder if Anderson and Hunt really actually examined flowering specimens or in some cases ANY actual specimens.

        In several cases, the mergers were published by people who seemingly lacked first-hand examination of the material. For instance the peculiar assertion that the slender, densely branching Trichocereus uyupampensis Backeberg and the stout, solitary columnar Trichocereus validus sensu Backeberg are synonymous.

        When faced with this situation we would suggest to botanists that they should not be afraid to say “I don’t know” or at least search out bona fide materials before uttering such pronouncements in print.

        What is perhaps most fascinating is the movement within the Opuntioidae towards lumpy definitions of the species accompanied by a splitter’s view of the genera.

Family: Cactaceae

    Subfamily: Pereskioideae 

Pereskia corrugata 

Pereskia tampicana

    Subfamily: Opuntioideae 

Cylindropuntia acanthocarpa 

Cylindropuntia echinocarpa 

Cylindropuntia imbricata 

Cylindropuntia spinosior 

Opuntia basilaris 

Opuntia ficus-indica 

Pereskiopsis scandens

    Subfamily Cactoideae 

        Tribe Browningieae 

Stetsonia coryne 

        Tribe Cacteae 

Aztekium ritteri 

Lophophora diffusa 

Lophophora fricii 

Lophophora williamsii 

Turbinicarpus lophophoroides 

Turbinicarpus pseudomacrochele subsp. krainzianus 

Turbinicarpus schmiedickianus subsp. flaviflorus 

Turbinicarpus schmiedickianus subsp. schwarzii 

Pelecyphora aselliformis 

        Tribe Notocacteae 

Eriosyce islayensis 

        Tribe Pachycereeae 

Polaskia chende 

Pachycereus gaumeri 

Stenocereus beneckei 

Stenocereus eruca 

Stenocereus stellatus 

Stenocereus treleasei 

        Tribe Trichocereeae 

Gymnocalycium asterium 

Gymnocalycium baldianum 

Gymnocalycium calochlorum 

Gymnocalycium carminanthum 

Gymnocalycium denudatum 

Gymnocalycium gibbosum 

Gymnocalycium leeanum 

Gymnocalycium mesopotamicum 

Gymnocalycium monvillei 

Gymnocalycium monvillei subsp. achirasense 

Gymnocalycium monvillei subsp. horridispinum 

Gymnocalycium netrelianum 

Gymnocalycium oenanthemum 

Gymnocalycium paraguayense 

Gymnocalycium quehlianum 

Gymnocalycium ragonesii 

Gymnocalycium pflanzii var. riograndense 

Gymnocalycium stellatum 

Gymnocalycium striglianum 

Gymnocalycium triacanthum 

Gymnocalycium uebelmannianum 

Gymnocalycium valnicekianum 

Gymnocalycium vatteri 

Echinopsis lageniformis 

Echinopsis cuzcoensis 

Echinopsis fulvilana 

Echinopsis macrogona 

Echinopsis pachanoi 

Echinopsis peruviana 

Echinopsis peruviana subsp. puquiensis 

Echinopsis santaensis 

Echinopsis schoenii 

Echinopsis scopulicola 

Echinopsis strigosa 

Echinopsis tacaquirensis subsp. taquimbalensis 

Echinopsis terscheckii 

Echinopsis thelegona 

Echinopsis uyupampensis 

Echinopsis volliana 

distribution; Lophophora williamsii echinata
Lophophora williamsii echinata


 

Distribution of alkaloids *within* cacti.

 

    Surprisingly there has been very little serious work published on this topic.

    Alkaloids in “pellote” (i.e. peyote) were reported by JANOT & BERNIER 1933 to be almost exclusively in the internal cells of the cortical parenchyma at top of plant. (See TLC results by Todd elsewhere here.)

    In Trichocereus candicans alkaloids were found by Niedfeld to be mainly in the chlorophyllaceous cortical parenchyma. (Niedfeld used microchemical methods to determine this) RETI 1950 cited NIEDFELD 1931.

    In T. terscheckii; alkaloids are primarily in the parenchymal tissues, 29% were found to be in the green epidermis (dry), while the central parts (dry) including cortical parenchyma contained 45% of the total alkaloid content [please note that this included the vast majority of the parenchymal tissues and the total weight of that portion of the plant is much higher than that of the green epidermis. This indicates a lower concentration for the central parts than in the green portion but potentially useful concentrations nonetheless.] RETI & CASTRILLÓN 1951

    Parenchymal tissues are highly specialized thin-walled storage cells that exist within in the thick outer layer on the plant. They are the site of many metabolic processes and also store such things as water, calcium oxalate crystals and often alkaloids.

    Calcium oxalate crystals are said to be stored in abundance in some peyote specimens. A nice image of showing their presence inside of the flesh of peyote can be found in the entry for Lophophora williamsii.

    As far as I can determine, the parenchymal tissues extend from near the skin to the vascular bundle; including most of the tissues other than vascular, structural or connective.

    Cortical parenchymal tissues are those towards the outside. Chlorophyllaceous just means that they have chlorophyll (are green.)

    Obviously, when a peyote button is sliced into two horizontal portions, they will be slightly more prevalent in the top half of the button than the bottom half of the above ground portion due to the relative percentage of tissue which is occupied by the central vascular tissues and by the outer layer. Published analytical work reflects this (see under Lophophora williamsii chemistry.)

    A similar picture was reported in Kircher 1972 for triterpene glycoside distribution within the flesh of the organ pipe cactus Lemaireocereus thurberi:

Tissue % of total Methanol soluble product
Epidermis 4
Photosynthetic layer 42
Transition zone 28
Cortex 12
Pith 10
Wood 3

       

   As there is considerably more weight to the central parts than the green portion, the observations from RETI & CASTRILLÓN 1951 provide some support to the idea common amoung users that the highest mescaline concentration is within the green tissues on the periphery of the plant.

   Less” does not mean that there is no alkaloid in the whitish tissues beneath it. All evidence suggests that there is ample alkaloid contained in these parts, just significantly less than in the green layer. It is also likely there is even less in the central vascular bundle and core itself.

   Another interesting result was noted among SMOLENSKI and coworker’s multitude of general alkaloid screenings. When testing Pachycereus pecten-aboriginum they reported Roots: ++, Stems: – and Ribs: +++. As slicing off the ribs would remove most of the cortical tissues this is in line with the above observations. Their account provides no further information on tissues evaluated (samples provided to them as a previously prepared extract).

   There is additional support for this; DJERASSI et al. 1953b determined that the majority of the alkaloid content in Lophocereus schottii was in the green epidermis (6.7% crude alkaloid); only a minor portion in the cortex (1.1% crude alkaloid) and almost no alkaloid in the core & pith (0.2% crude alkaloid).
   By cortex Djerassi means the epidermis, by green epidermis Djerassi refers to the chlorophyllaceous parenchyma. Djerassi was a natural products chemist not a botanist.
The casual and nonconsistent use of the words epidermis and cortex has caused confusion for many readers who did not stop and ask what was being actually meant by the user of those particular words and instead translated them based on what they themselves would have meant by those words.]

   Anderson described TODD 1969 as finding little difference [qualitative] between the alkaloids of root and top in peyote except for hordenine which was only present in the root. While true in most aspects, this is a little misleading as concentrations in the roots are far lower than in the tops. Please see more details under the Lophophora williamsii entry. [In Sacred Cacti 3rd ed. Part A or in Sacred Cacti 2nd ed.]

   This is also in at least partial conflict with the reports of other workers.

   Todd collected his samples during June. Curiously, lophophorine was apparently observed as the major alkaloid in L. williamsii. [See also comments on the seasonal fluctuations of alkaloids in peyote.]

   GUTTIERREZ-NORIEGA 1950 (citing CRUZ SÁNCHEZ 1948) appears quoted as saying that the alkaloids are primarily in the “bark” of T. pachanoi. His word, corteza, translated in the English summary as bark, also means ‘cortex’ or ‘skin’ in Spanish.

    Apparently CRUZ SANCHEZ worked with the outer layer due to the slime resulting from use of the whole stem interfering with his extraction procedure. He reported 5% in the dried outer layer.

   This area needs further work. While many alkaloids may indeed be higher towards the outside of the plant there are known exceptions. Hordenine being observed in the root rather than the top (in peyote) is a good example. Its highest concentrations being in the root was reported again in Mammillaria microcarpa by KNOX and coworkers.
It is noteworthy also that all of the alkaloids measured by KNOX were much higher in the cortex itself as compared to the chlorophyll rich tubercles and several were higher in the vascular tissues than in the tubercles.

      An Entheogen Review reader wrote to say that they had found an unspecified amount of the cores of San Pedro to be active but they provided inadequate information for us to understand HOW they actually determined this or how much they observed.

   This should not be any surprise should a person ingest a large enough amount.

   PUMMANGURA et al. 1982 reported that mescaline did not transmigrate between grafted T. pachanoi and T. spachianus regardless of which was used as stock and scion. Their conclusion was that mescaline was locally produced and noncirculating.

   While it may or may not be true that transmigration of alkaloids does not occur, SINISCALCO 1983 reported that the normally mescaline-free Myrtillocactus geometrizans was found to contain 0.3% mescaline by dry weight after having previously been grafted with Lophophora williamsii.

   Many questions immediately arise. None are presently answerable.
Trichocereus scopulicola NMCR

Trichocereus scopulicola FR991 seedling (NMCR); from Ritter’s species but using seed acquired from Riviere de Carault.

In an odd e-mail that I received in 2004, Karel Knize commented

        “Some flowers are used (cont ca 4%) plant itself 2-3.5%
the strongest type are 9-12 ribs or 3-4 ribs
Knize did not elaborate further (and I’d suggest this be taken with a large grain of salt). 

        A friend has claimed to have had good results from the flower masses they collected from peruvianoids and terscheckii but preserved no details.
In more recent years, additional friends ingesting pachanoi and peruvianus flowers and ovary could discern no effects whatsoever.  Clearly some analytical work seems in order to know what to believe.
There IS something that perhaps may be true? In evaluating the reports of human bioassays it is always important to be able to identify and preclude the contributions from any “non-negative placebo responders” (to borrow Jim Ketchum’s wonderful phrase).

        It is almost unbelievable that no one has looked into the matter of alkaloid distribution within cacti more thoroughly.

        The analysis of only the outer green layers and only looking at only mescaline has become the predominate analystical approach. This is for practical reasons not a reflection of a fixation on mescaline.
        The reasons are simple:
1. It is easier to work with the slimy inside of the cactus if only the outer green layer is used.
2. Most researchers would LOVE to look at every alkaloid in their plants but due to a lack of reference materials the necessary standards are simply not available through commercial sources. Out of the 63 alkaloids reported from peyote, for example, only 5 or 6 can be obtained from fine chemical houses.
        Historically workers doing structural analysis would accumulate and save their purified alkaloids. These were then shared with other people doing the same work. When they were still active in research, Jerry McLaughlin & Arnold Brossi were the actual reference standard resources for multiple other workers.
        Synthesis is also possible but the actual cost and ability to create an functional set of basic cactus alkaloids reference standards via synthetic means is out of the reach of the average grad student performing analysis on the alkaloids of a plant. Mescaline, by contrast, is relatively easy to obtain as a pure reference standard so it now tends to be the only target being identified and quantified.

 

 

Trichocereus scopulicola Oz

 

Trichocereus scopulicola grown from seed in Oz. All of these originated as FR991 seed that were acquired from Ritter’s sister Hildegarde Winter but Australian cactus producers have been generating and relying on their OWN domestic seed production from the *plants* that were produced from Winter’s seeds since the 1960s.

 

 

Islaya

Islaya minor Backeberg

Curt Backeberg (1934) Kaktus-ABC 258, as Islaya minor
Carl Friedrich Förster (1861) Hamburger Gartenz, 17: 160, as Echinocactus islayensis.
Fred Katterman (1994) Succulent Plant Research, 1: 117, as Eriosyce islayensis.

Ritter_1981_3_1185_Islaya_krainziana_ill

Image above is from Ritter. I have not been able to locate who owns Ritter’s copyrights so have not obtained permission for the use of this image. If someone can give me more information on how to organize formal permission it is most welcomed or if the presence is objectionable it will be removed promptly.

 

According to Anderson 2001, all of the former genus Islaya has been merged as a highly variable Eriosyce islayensis (C.F. Förster) Katterman.

Mescaline present in trace amounts (0.0017% in dry plant)

Origin: Found in southern Peru (above Mollendo, dept. of Arequipa). [Named for the town of Islaya.]

Habitat: Arid, dry desert regions with little rainfall. Mineral rich alluvial sediments, on sand dunes and exposed windy slopes. Most moisture is derived from fog.

Forms simple (unless apically damaged) short plants up to 13 cm tall and 7 cm wide.

Ribs are 6 mm in height and number around 17. The areoles initially bear whitish-grey felt.
Spines are rigid black, later becoming grey.
There are 20 to 24 six mm long thin radial spines and 4 cruciform (usually) centrals which are stouter, thickened below and up to 18 mm [20 mm] long.
3/4 inch [2-2.2 cm.] flowers arise from the felted area and vary from golden to light greenish-yellow.
Hairy, carmine fruit starts globular and ripens elongated. Perianth and a few bristles persist on the top of the fruit.
Backeberg 1977 page 217.
and Pizzetti 1985 Entry #137. (Pizzetti has a color picture with fruit.)

These are represented in collections as beautiful but small and slow growing specimens.

Backeberg notes that wild collected plants of Islaya are sometimes difficult to grow.

Reported analysis of Islaya

Mescaline was present at 0.0017% in the dry plant. (tlc, gc)
3,4-Dimethoxy-β-phenethylamine present at 0.0038% in the dry plant. (tlc, gc)

 

Also observed but did not quantify (using tlc only):
β-Phenethylamine
Hordenine [N,N-Dimethyltyramine]
3-Methoxytyramine
N-Methyltyramine
Tyramine [4-Hydroxyphenethylamine]
Pellotine [6,7-Dimethoxy-1,2-dimethyl-8-hydroxy-1,2,3,4-tetrahydro-isoquinoline]
Corypalline [7-Hydroxy-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline] (The only reported occurrence of this alkaloid within the Cactaceae)
Doetsch et al. 1980

 

 

 

External links:

Dave’s Garden’s
IPNI
ThePlantList
Tropicos