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

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

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

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

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

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

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

Dr. Clement has commented about being unaware of any controversy or questions existing about their work (as has Forbes) but this appears to be in conflict with at least two professional workers (Dr. Alexander T. Shulgin & Dr. Martin Terry) who voiced comments to me about their experiences with Dr. Clement while they were still trying to learn answers for the questions they had noticed. Shulgin was in California and attempted to contact her both by phone and by snail mail. Terry was then at the same institution as Clement  (Texas A&M) working on his third PhD. He described unsuccessfully to arrange a conversation with her despite knowing each other from prior to this.

It is worth carefully reading the words from Clement appearing in the various published accounts.

In 2013, an interview with Dr. Clement appeared, in which she defended their reported data and described the elaborate precautions that were said to be necessary in order to produce the same results. (Such as performing the extraction and solvent removal using the protection of an argon blanket.)

To be fair to Dr. Clement, it is noteable that no one at FDA actually tried to replicate her work rather than apparently rejecting the precautions taken to prevent degradation as being unnecessary. I may agree with the *conclusions* of her critics but I would also suggest that, thus far, no one can legitimately claim that anyone actually attempted to replicate what was reported in Clement et al. 1997 and 1998. For the most part, Clement began by extracting fresh (1997) and fresh and still frozen (1998) plant materials, whereas Pawar et al 2014 freeze-dried their fresh plant samples. (Clement had used freeze-drying of fresh frozen leaves for quantification of N-methylphenethylamine.) Pawar also omitted the use of argon which Clement presented as important to prevent degradation of alkaloids. However, Pawar’s interest was not an academic one trying to reproduce Clement’s results but rather was the result of FDA interest and was focused on establishing what compounds were in the diet products they also tested — and whether those contents came from this plant. Their point of study really had no reason to respect the concerns voiced about the degradation of alkaloid content. And to be fair to her critics, Clement did not describe the needs for such protection within her two accounts with nearly the same amount of details as she did within that 2013 interview. (The pertinent comments from those papers as concerns argon can be found quoted farther below.)
One point which might be missed in Clement’s comments asserting the need for protection with argon. Many of the alkaloids presented as being prone to degradation are actually known to be quite stable. As much or even more so than the alkaloids that both others and Clement have found. In some cases the purported fragile molecules, such as mescaline, have been shown to persist in archaeological finds for millennia. There are also some contradictory comments from Clement appearing in print that, when compared with each other, cast further shadow on the accuracy of their published results.
A clear need for confirmation is evident; especially considering the failure of anyone to replicate any of their novel results.

In that interview (which now appears to be offline?) there are a number of things the careful reader might notice as being peculiar for sake of not being mentioned at all, such as their discovery of a wealth of novel Acacia alkaloids.
There are also some words included in that interview that are worth noticing (and worth comparing to the published details):

“The early season guajillo was unremarkable to Clement and her team. “The extraction was clean (bright green extract, easily partitioned with acid and base extraction),” Clement reported. “The analysis was relatively straightforward; we found terpenes, a few simple phenols and scant traces of β-phenethylamine, but no detectable N-methyl-β-phenethylamine, which had previously been reported.” However, work on late season guajillo was a different story. “The initial methanol extract was a very dark green, almost black color,” she noted, adding the team realized these extracts had to be handled much more carefully due to extreme vulnerability to degradation. “After we began using an argon blanket, this degradation was no longer a problem; argon is a much more forgiving inert atmosphere than nitrogen.” The end result was positive identification of N-methyl-β-phenethylamine; N,N-dimethyl-β-phenethylamine; and tyramine in these fractions.”
INSIDER, November 26, 2013 written by Steve Myers.
Online at http://www.naturalproductsinsider.com/articles/2013/11/blackbrush-scapegoats-or-shaky-goats.aspx  (Accessed on 17 May 2014; still online in January 2015 but not in 2023)

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

Acacia berlandieri Bentham (these results should be questioned)

Clement et al. 1997

Acacia rigidula Bentham (these results should be questioned)

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

Clement et al. 1998

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

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

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

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

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

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

Published analytical accounts for Acacia berlandieri.

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

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

Camp & Lyman 1957 reported the recovery of 0.5% of N-Methylphenethylamine by dry weight and published a synthetic approach.

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

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

Camp et al. 1964 reported N-Methylphenethylamine in Acacia berlandieri along with two additional alkaloids:
Tyramine & N-Methyltyramine.

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

Enzman 1968 was simply a review summarizing the results of Adams & Camp 1966 and Camp & Lyman 1956; adding some previously published identification criteria for their reported alkaloids (gleaned from elsewhere in the literature).

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

I have not yet obtained Forbes 1991.

Pemberton et al. 1993 was an account of an isolation approach for assaying Acacia berlandieri. Using plants collected in Zavala County, they reported Tyramine (1.71-1.94 mg per gm dry weight), N-Methylphenethylamine (0.24-0.27 mg per gm dry weight) and what they believed to be N-methyltyramine (3.01-3.28 mg per gm dry weight). They were unable to confirm their identification of N-methyltyramine due to lacking a reference standard for comparison but believed the identification was accurate.

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

Known errors, unknowns and questions

The following are some unanswered questions, including concerning a couple of reports about trace amounts, and the assorted known errors that have been encountered in the literature or online mistakenly asserting the presence of mescaline.

There is also a couple of additional cacti included that are in need of some comment concerning questions they present.
These are not discussed in detail within this work (that can be found in Sacred Cacti part C, section 2 Cactus Chemistry By Species [PDF]) but I wanted to create a summary of them here for the convenience of the reader.

Abraham Caycho Jimenez’s claims in particular should be viewed with caution due to his lack of verifiable references and wealth of misspellings.

In this presentation, I have decided to alter what existed in the book Sacred Cacti. The reason being these entries partially overlap with the corresponding species entries in Cactus Chemistry By Species.
As that book is also coming to this webpage in its entirety (and is already online in PDF form) it made more sense to recombine all of the longest examples of those particular entries into a single entry each in Cactus Chemistry By Species. Those will be linked to from this re-edited page that can serve as an illustrated overview. Until that web addition is complete please use the PDF version of that work.

There also is no point in creating a citation list dignifying the wealth of claims asserting variously that either all cacti contain trace amounts of mescaline or else all of the Trichocereus species contain trace amounts of mescaline. That is clearly an erroneous comment, at best.
Only a relatively few cactus species show trace amounts of mescaline, even fewer produce isolatable quantities of mescaline and only a relative few actually contain useable concentrations of mescaline. I have no doubt that more remain to be discovered but right now the cactus species which are known to contain pharmacologically meaningful amounts of mescaline number less than a dozen out of nearly two thousand cactus species. Similarly the number of genera presently known to have members which are capable of producing useable concentrations of mescaline is two out of more than a hundred.

Acacia berlandieri
Acacia rigidula

There are problems in these accounts which raise questions about the actual validity of Clement’s claims for mescaline in these two legumes. More noteable has been the failure of other workers, whether before or after Clement, to replicate their reported results. [Summary of the reported chemical analysis for these two species and a more detailed discussion.]

Descriptions, characteristics & illustrations:
Acacia berlandieri
Acacia rigidula

Armatocereus laetus

Strange and unreferenced comments have appeared asserting the presence of mescaline in this cactus.
They are all erroneous.
An email conversation with Wade Davis and with Dennis McKenna established that the phytochemical analysis alluded to in Davis 1983 had never been performed and that mescaline was not reported.

Some of the claims that it contains mescaline may simply be based on Wade Davis proposing it to be considered a San Pedro cactus that is sometimes used for brew preparation.

This species has also been found to be inactive in unpublished human bioassays. It presently lacks an analysis other than a less-than-ideal screening for alkaloids by Carl Djerassi. Using material that had been wild-collected in Peru, he concluded that it was almost devoid of alkaloids or triterpenes. Djerassi et al. 1955b

See Part. C sect. 2 Cactus Chemistry By Species or Part B San Pedro for more details.
The latter PDF is several years old now so if you encounter problems with it be sure to turn off your PC’s attempts to open it in ‘safe mode’ (the new security default setting in Windows distrusts any file made by a version of Acrobat prior to having the newer security upgrades). If anyone has problems opening this with a Mac let me know.  That has been the only conflict reported so far.

Carnegiea gigantea (Engelmann) Britton & Rose

The assertion that mescaline was reported is erroneous.
It has never been found to contain mescaline.
The claim is not supported by any of the references that it included. [i.e. Agurell 1969b, Kapadia & Fayez 1970 J. Pharm Sci. 58:1158, and Mata & McLaughlin 1976 Lloydia 39(6):461.]
It APPEARS to possibly have arisen due to a misreading of a dense paragraph in Agurell 1969b by a worker for whom English was a second language.
A surprising number of analytical reports have been published for saguaro. NONE of them have reported mescaline. See Cactus Chemistry By Species for more details.

Cephalocereus melanostele Vaupel

Cephalocereus sp. (?) Pfeiffer

The claim for the presence of mescaline is made by Caycho Jimenez 1977 (page 91) but no reference was cited and nothing was included to support his assertion.

Cereus acranthus Vaupel  — now Haageocereus acranthus (Vaupel) Backeberg

The claim for the presence of mescaline is made by Caycho Jimenez 1977 (page 91) but no reference was cited and he does not include anything to support his assertion.

See more comments under T. cephalomacrostibas below and in Cactus Chemistry By Species.

Cereus peruvianus Haworth

Cereus sp. Miller

The claim for the presence of mescaline is made by Caycho Jimenez 1977 (page 91) but no reference was cited and he does not include anything to support his assertion.
It may be important to recall that pachanoids have historically been sold as Cereus or Cereus peruvianus (including in Peru).
It is however pertinent to note that this claim most likely resulted from Rouhier 1927 (and/or Soulaire 1947’s retelling) who made this claim in print based on comments from Cobo but careful reading will reveal Cobo was actually talking about T. pachanoi.

See more images and some additional details in Cactus Chemistry By Species.

Coryphantha macromeris (Engelmann) Lemaire

Coryphantha runyonii Britton & Rose

Claims for mescaline’s presence in these two species appear in the literature erroneously.

BBB presents Coryphantha macromeris as a mescaline containing cacti for no clear reason; perhaps assuming that rumors of use must mean that mescaline is present?
The first species has been purported to be a mild hallucinogenic plant in its own right.
That particular claim arose in Ott (1976 Hallucinogenic Plants of North America) who cited his own unpublished lab notes and Jerry McLaughlin, unpublished data, as his references. Schultes & Hofmann included Ott’s observation in Botany & Chemistry of the Hallucinogens and in Plants of the Gods. However, in his later works, such as Pharmacotheon, Ott strangely began citing Schultes & Hofmann’s secondary reference (to him!) and ceased to include mention of a reference to either himself or to Dr. McLaughlin.
Bioassay of Coryphantha macromeris produced mild but weird effects followed by persistent after-effects. I certainly have no intention of bioassaying it again.
See more details within the entries for normacromerine and macromerine in Sacred Cacti Part C, section 1, Cactus Alkaloids.

Coryphantha runyonii appears to be listed seemingly for nothing more than being considered to be a varietal form of Coryphantha macromeris.
Neither species has ever been reported to contain mescaline based on analysis or bioassay.

See more images and some additional details in Cactus Chemistry By Species.

There is also an account appearing finding mescaline in a compounded herbal formulation that was shown,  through the use of cDNA primers, to contain Coryphantha macromeris. Analysis of actual plant material showed that the mescaline came from a different source and was not from Coryphantha macromeris. The mescaline containing plant source was not identified but the herbal extract was found to additionally contain Turnera diffusa (damiana) and Peganum harmala (syrian rue). Hiroyuki Kikuchi et al. (2010) Forensic Toxicology, 28: 77-83.

Coryphantha palmeri (Engelmann) Britton & Rose (now C. compacta)

Coryphantha radians (A.P.deCandolle) Britton & Rose

Trace amounts of mescaline are seemingly implied to have been detected in these two species but the wording of the account is unclear and does not specifically state it. Gennaro et al. 1996

See some additional details in Cactus Chemistry By Species.

Epiphyllum sp.

The claim for the presence of mescaline is made by Caycho Jimenez 1977 (page 91) but no reference was cited and nothing was included to support his assertion.

See more images and some additional unrelated details in Cactus Chemistry By Species.

Gymnocalycium fleischerianum Backeberg

Mescaline (0.0001-0.001% dry wt.) ?
Štarha 2001c did not include a citation for this information. (Furthermore, G. fleischerianum was included only in the table on p. 91 and not in the ‘by species’ breakdown that was presented earlier in the same work.)

Melocactus peruvianus Vaupel

The claim for the presence of mescaline is made by Caycho Jimenez 1977 (page 91) but no reference was cited and nothing was included to support his assertion.

Additional details are in Cactus Chemistry By Species.

Myrtillocactus geometrizans (von Martius) Console

This species appears in the literature erroneously.
Mescaline is not present.
0.3% dry wt. appears to be listed as being isolated from plants previously used as stocks for grafting Lophophora williamsii but G. Siniscalco Gigiliano contradicts this in his experimental account (Siniscalco Gigliano 1983).

Neoraimondia macrostibas (K.Schumann) Britton & Rose

The claim for the presence of mescaline is made by Caycho 1977 (page 91) but no reference was cited and nothing was included to support his assertion.

I suspect he may have been assuming the presence of mescaline extrapolating from an earlier report by Guttierez-Noriega that it was incorporated into a shamanic brew called cimora. (See additional comments in the Sacred Cacti Part B San Pedro.)

Opuntia (Austrocylindropuntia) cylindrica

The claim for the presence of mescaline was based on Trichocereus pachanoi misidentified as this species. See more details within its entry.

Opuntia pachypus K.Schumann [sic as Opuntia pachiypus]

Opuntia sp.

The claim for the presence of mescaline is made by Caycho Jimenez 1977 (page 91) but no reference was cited and nothing was included to support his assertion. See some images of Austrocylindropuntia pachypus within its miniscule entry.

More unresolved questions concerning some cacti claimed to contain mescaline

More images and detailed comments concerning these (and  discussions of the assorted cacti additionally reported or purported to be psychoactive for reasons other than mescaline) can be found in Cactus Chemistry By Species in the section entitled “Activity & Mythology“.)

Five San Pedros

All 5 of these are purported to be known as “San Pedro” and are further claimed to be used by Peruvian shamans for making their brew.
Compare the one on far right to Armatocereus laetus which can be found pictured farther above. And notice the Haageocereus?

At risk of being accused of being cynical, I was struck with an unanswered question as to whether the person assembling the “5 San Pedros” did so based on actually encountering them in use by shamans or if they did so based on their interpretation of the published literature. This same person was also the source of “huallanca” and several other oddities.

More words and many more images can be found in the PDF Cactus Chemistry By Species.

Stenocereus hystrix

There is a claim for the presence of mescaline in something that is being sold under the name Stenocereus hystrix. And there are reports of activity in dried material said to be from this plant (curiously no reports yet from people ingesting material from the cuttings).
That identification appears to be plausible to me (that is an image above) but flowers are needed for a conclusive determination AND there are some odd discrepancies meriting some comments.
It is a commercial ethnobotanical offering purported to be potent with a 20 gram dose of outer tissues (dry weight). Some of the same material was said by the vendor to be weaker due to being harvested after water was abundant.
It is also claimed by its vendor that only one stand of this species is active and that all of the other occurrences in the Dominican Republic are inactive. This last point has caused the supplier to further suggest that it might be a hybrid but it is unclear what they thought it was crossed with or why it being a hybrid would cause it to become mescaline containing.
More work is needed as Djerassi had reported Stenocereus (as Lemaireocereus) hystrix to be devoid of alkaloid. I would feel a lot more comfortable with thinking there may be something to this claim if not for the incredible problems that arose both times when attempting to procure live material to identify and then analyze (in all attempts what came were infected with a rapidly fatal disease; one was already dead upon arrival). Dried material said to be from this species was readily available by comparison.  My gut feeling is that it is this CLAIM that probably is in need of some closer scrutiny as, so far as I have been able to determine, both the cuttings and the dried material are produced in the Dominican Republic on the vendor’s behalf by a third-party rather than by the vendor.

An actual entry for Stenocereus hystrix will soon exist but until then, references, more images of authentic Stenocereus hystrix & Djerassi’s meager analytical details can be found within the work Cactus Chemistry By Species.

Trichocereus cephalomacrostibas (Werdermann & Backeberg) Backeberg

[AKA Haageocereus cephalomacrostibas or Weberbauerocereus cephalomacrostibas]
The claim for the presence of mescaline is made by Caycho Jimenez 1977 (page 91) but no reference was cited and nothing was included to support his assertion.
Material appearing similar to this species or Haageocereus acranthus has been purported to be used by Peruvian shamans (Anonymous 2005; see image below that was mislabeled T. spachianus). [See images and additional comments above or in its entry in the PDF Cactus Chemistry By Species.]

Trichocereus tulhuayacensis Ochoa

The claim for the presence of mescaline is made by Caycho Jimenez 1977 (page 91) but no reference was cited and nothing was included to support this assertion.

The presence of mescaline would be far from surprising but this species presently lacks any analysis or bioassay reports.

Trichocereus sp.

I presently do not know the correct identification of this plant.
It has features that resembles bridgesii, uyupampensis and knuthianus but is not really a nice fit for any.
This plant has been proven to be a mescaline container through human bioassay. Correspondent requesting anonymity.

My none-too-great photos were taken of the plant growing in Tom Juul’s garden just prior to its destruction to prepare space for construction. 

Unknown cacti in the Chaclayo market.

The person taking this photograph did not acquire any information about what these plants were sold for. (I am referring to the many ribbed cacti that are displayed with the normal San Pedro tips.)

There is presently no suggestion they contain mescaline and no indication of their intended use. They could have been sold simply for use as a hair rinse as is a common use for other columnar cacti.
There are some assorted loose threads that cause these to be intriguing to me and I would suggest that it would be worth someone following up on this report and learning their intended purpose no matter what that turned out to be.  Please let me know and I’ll update this accordingly.

Polaskia chende (Gosselin) Gibson & Horak

Mescaline is present in trace amounts.

Common names: “chende” and “chente” and “chinoa”. First was included by Pizzetti, first two by García and all three by Britton & Rose. Roland-Gosselin also gave “chende” but added the Nahautl name “cotzonotsehtly“.

Etymology: Polaskia is a name honoring the cactus lovers Charles and Mary Polaski.
Heliabravoa is a name honoring Helia Bravo-Hollis, the Mexican botanist.
Lemaireocereus is a name honoring Charles Lemaire.
chende is derived from “chende” which is its folk name.)

Distribution & occurrence: Found on the Cerro Colorado and also near Acatepec (in Puebla) Jorge Meyrán García 1973; Occurs in Puebla (near Tehuacán and Tepeojuma) and Oaxaca (Oaxaca de Juarez 1500-2200 m; Rio de Oro Canyon near Tamazulapan, 1750m) in Mexico. Backeberg 1960.

 

Original description of Robert Roland-Gosselin (translated into English):
“This species was discovered growing in places 2,000 meters or more above sea level at Cerro Colorado, near Tehuacan. It bears the indigenous Mixtec name of Chende. According to Mr. Diguet, the Nahuatl name is Cotzonotsehtly, meaning “yellow cactus”.
From about one meter from the ground, it ramifies much and forms, by the piles of the branches, a kind of umbrella.
The photographs show specimens of about 6 meters high, with a much larger diameter at their summit.
The branch observed was 11 centimeters in diameter, seven 3-centimeters deep ribs, subacutely crenellated, not furrowed laterally; their sines forming angles of 90 degrees. Areoles spaced 25 mm apart, placed at the bottom of the notches; They are felted, prominent, and round. 6 Radial spines that are less than 2 cm. The lower spines are longer than the higher spines. All are subulate, starting out, soon becoming gray. No central spines.
Flowering occurs on younger areoles of the previous growth. Pointed buds are covered with brown bristly hairs.
At anthesis, the ovary is nearly spherical, about 12 millimeters in diameter, emerald green, and covered with tight little tubercles, between each of which has a noticeable areole with abundant slender sharp, rigid, brown spines, sometimes up to 4 inches long, interspersed with short wool that is fine & reddish.” (continued below)

“Fleshy receptacle is very short, not more than 1 centimeter. It is covered with green scales that are overlapping & triangular, terminating as a thin brown mucron that is scarious in texture, sometimes 7-8 millimeters long.
The sepal scales are red to pinkish with a white edge, ending in spikes similar to those of receptacle scales.
Sepals are an inch and a half long by 5-6 mm wide, bright carmine red on the outside, much lighter inside, terminated with a brown tip 2-3 millimeters in length.
Petals are as two rows, the same size as the sepals, forming a spread of 4 centimeters in diameter. The outer row is pink outside, white inside. The inner row is pinkish white on both surfaces. They all terminate in a short brown tip.
Long light yellow stamens of 1o to 15 mm are inserted in steps over the length of the receptacle, with light yellow anthers.
Style is stout, 22 millimeters long, yellowish white, with 11  stigmata, 7-8 mm long, spreading, exceeding the stamens in length.
Nectar chamber is 5 millimeters long, full of syrupy liquid.
The flower gives off a strong enjoyable perfume.
The ripe fruit is pungent and edible, and sold in Mexican markets. It is of the size of a small walnut, covered with brown spines, resembling a sea urchin.
According to Mr. Diguet, the fleshy part of the internal stem is a saffron yellow color, extremely rare in the other species of Cereus. This exceptional trait had not escaped the notice of the aborigines, since, as I said earlier, the Nahuatls referred to the plant as the “yellow cactus”.
The seed is black, very small (1 mm long and 1/2 millimeter wide), finely pitted, subventral hilum is appressed.” pp 505-506, Roland-Gosselin (1905) (The above was adapted from the French original.)

Large, many branched plant, 5 to 7 meters tall [to 23 feet]. Often with a short trunk.

Slender branches with 7 to 9 sharp ribs.

Areoles on older branches are 1.5 cm apart but may be closer on
young growth.

Spines are brown to bright yellow turning grey with age. There are usually (2-3) 5 radial spines (1-2.5 cm long) and the centrals (1-2) are a little longer but not always present.

Flowers are rose colored and about 3 to 4 [-5] cm long.

Fruit is 4 cm in diameter, deep red and very spiny [with light brown hairs.].

Seeds are 1 mm long.

Description drawn from: Backeberg 1960 4: 2157-2159 (as Heliabravoa pp. 2155-2159) and Britton & Rose 1920 2: 90-91 (as Lemaireocereus).

Pizzetti 1985: Entry #134; as Heliabravoa. Has color photograph.

It is the source of an edible fruit. García 1973.

Backeberg 1960: picture page 2156, fig. 2036, with flower on page 2157, fig. 2038. Flower close-up page 2157, fig. 2038.

Britton & Rose 1920 Vol. 2: 91; picture: fig. 133.

Color picture in habitat on page 59, figure 50 of Ríha & Šubík 1981.

See also figure 3 of García 1973.

 

 Reported analysis:

Mescaline and DMPEA were both indicated to be present at less than 0.01% by tlc while the tandem MS estimate was 0.01%.

3,5-Dimethoxy-4-hydroxyphenethylamine estimated at 0.01% (tlc and ms-ms).

     Ma et al. 1986

Shamma & Rosenstock 1959 did not report any alkaloids but did isolate and identify the following triterpenes:
Oleanolic acid
Oleanolic aldehyde (First reported occurrence in nature.)
Erythrodiol

 

 

Seedlings are commercially available.

the supergenus Opuntia

Opuntia is said to be derived from Opus, capital of Locris in ancient Greece (apparently due to some sort of a plant which grew near there) [Note 37].

Some years ago the Opuntias existed as many smaller genera. It was then lumped together into an unwieldy supergenus. It is now subdivided again, largely back into the same genera as before. It would be interesting to somehow be able to total how much time, human labor and resources were wasted by those two sets of name changes. I really feel for the academic & scientific indexing services.

This part of the larger work only includes a few of the Opuntia species. Most are included due to being reported to contain trace amounts of mescaline but the first two owe their inclusion to being erroneously claimed to contain mescaline.

The species with entries in Part A:
2 Austrocylindropuntia species (AKA Opuntia cylindrica & Opuntia pachypus)
Cylindropuntia species
Opuntia (Platyopuntia) species

Many more species are discussed in terms of their reported chemistry in Cactus Chemistry By Species.

A number of Opuntia species are featured in supernatural context in a wide variety of archeological depictions crossing many cultures and years. Most appear to be either small jointed or round jointed. In some cases the small jointed depictions are also distinctly spotted as can also be readily observed in a number of the Tephrocacti which bear dense round clusters of short glochids.

One curious example [Note 33], involving possible enema paraphernalia, shows a male and a female jaguar with clearly dilated pupils, each with four prickly pear pads portrayed on each of the necks of the stirrup vessel above them. A jaguar with dilated pupils is similarly distinctly depicted in the context of San Pedro cactus on a much more intricate stirrup vessel (which has been reproduced numerous places including Schultes & Hofmann’s Plants of the Gods. These vessels were made in molds and assembled. There are at least six distinct variants existing of the jaguar and San Pedro cactus theme with multiple copies being known.

The following image is from the Walters Art Museum.

Walters Art Museum [Public domain, CC BY-SA 3.0 (http://creativecommons.org/licenses/by-sa/3.0) or GFDL (http://www.gnu.org/copyleft/fdl.html)], via Wikimedia Commons

Use of some forms of stirrup vessels for enema administration has not been proven (or even particularly well explored) but it may be pertinent to comment that one of the few depictions that I have encountered which depicts them in actual use,  portrays them as being used for this purpose [Note 34].

Very few Opuntia species have been analyzed. It is an enormous genus in need of phytochemical work. An interesting note was made in the 1949 Chemical Abstracts, when describing the work of Federico Falco and Sebastian Hilburg published in 1946/1947. They examined a number of Argentinean Opuntias. “The presence of alkaloid was demonstrated in every sample.” Clearly this is an area which deserves more attention.

The low mescaline content observed in the Opuntia species to date does not mean they all must be similarly low. Most Trichocereus species lack mescaline entirely and many which do contain it, do so in very low amounts. Even the high mescaline producers sometimes have only low concentrations.

As with  Trichocerei, most Opuntias have not been examined and the majority of plants such as Puna are also presently unexamined. However, a far lower percentage of the existing Opuntioid species have been analyzed compared to Trichocereus. And, only a trivial number of their close relatives, Maihuenopsis, Quiabentia, Pereskiopsis, Pterocactus and Tacinga, have; with trace amounts of mescaline reported in one Pereskiopsis species.