MDMA in Shulgin’s 'Cacti'

[M S Smith]

He's a draft that may end up being the final version. Please feel free to post elsewhere in forums or on a more permanent basis. Following the "essay" is a shot of the plant Sasha believed he tested, but it should be noted he told me he had some concerns over whether or not this is the actual plant of a few similar ones he tested.

~Michael~

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MDMA in Shulgin's 'Cacti'

Mind States Conference, 2002

By Michael S. Smith

At the 2002 Mind States Conference in Jamaica Alexander “Sasha” Shulgin gave a lecture simply entitled “Cacti.” The lecture has been available online for some time as an audio file and can be located at http://www.matrixmasters.net/blogs/?p=158.

What I tend to address are some of his comments regarding the Chilean Cactaceae species “Lobivia grandiflorus” and its chemical constituents that have possibly been misinterpreted by some who now believe this particular cactus contains MDMA.

Sasha brings up the subject of L. grandiflorus and MDMA early in the lecture and specifically notes a “peak of a trace component of MDMA” in L. grandiflorus and goes on to mention that it has the “same empirical formula...as MDMA.” But he clearly says about this “trace component” that if you “put the methyl group off the nitrogen and stuck it on the alpha position you’d have MDMA, same mass spectrometry.” This clearly indicates that MDMA is not in the cactus, but only that a closely related property is present that with some minor tweaking can be altered to MDMA. Not being a chemist myself, or one who even has a particular interest in it, and not knowing the lingo particularly well, I do understand that a “trace component of MDMA” doesn’t mean MDMA. The significance of “empirical formula” is not well understood by me, but I’m curious if in technical terms it indicates a broader grouping of chemicals rather than just one specific alkaloid.

After commenting on L. grandiflorus Sasha notes to the audience the importance of waiting “until tomorrow morning before you publish,” but then he slips and has one of the “senior moments” and “brain farts” he raises concern about at the outset of the lecture by asking how could it be that he might “find a little bit of MDMA in a cacti that grows in Baja, California, and halfway down the peninsula?” This is a “senior moment” because it is not L. grandiflorus that grows on the Baja Peninsula, but rather Pachycereus pringlei, a different cactus altogether that Sasha has been working with and has never made any claims of the presence of MDMA regarding. Sasha here is making a specific claim of locating MDMA in cacti, but not with the plant he was originally talking about.

So one can quite easily assume Sasha had a “senior moment” in saying MDMA is in P. pringlei, but I also believe he had a “brain fart” by simply saying at all that he found “a little bit of MDMA in a cactus.” But maybe not, depending on your perspective, as maybe his “little bit” isn’t relating to a specific alkaloid as many might think, but rather means that since there is a chemical structure in L. grandiflorus that is part of the make-up of MDMA the cactus itself thereby contains “a little bit” (a “trace”) of the chemical structure of MDMA, but not MDMA in its totality.

Caveats follow when he goes on to states that he “had not actually made MDMA in my laboratory for probably 15 years, but I could have simply have had a dirty beaker, I don’t know.” These comments, in addition to those about waiting to publish, show that even he doesn’t want to give too much credence to his own lectures reliability, but what is strange about this comment is why he would have to comment at all upon a dirty beaker when the more technical part of the lecture clearly argued against the presence of MDMA as a independent alkaloid present in L. grandiflorus. But then again, Mind States is not a conference of pharmacologists, it is rather a group of lay persons interested in the multifaceted subject of psychoactive drugs, and if you haven’t seen lecturers accentuate the more hypothetical aspects of their research then you haven’t attended enough lectures. And lastly Sasha remarks upon attempting to replicate the testing following “raising a sample of this cactus in hydroponics using nitrogen 15 nitrate only.” He states that if he “can get that same thing and get that same peak that has N15 in it then it has to be biologically synthesized.” Again this sort of talk is beyond my expertise, but I don’t think its offers any answers. The last comments regarding this subject before he goes off elsewhere is that “we probably won’t know for a year” what the follow up testing will find. Well needless to say, as of this writing it has been 6 years since the ”Cacti” lecture was given at Mind States, and I think that might be worth some consideration against the presence of MDMA in Lobivia grandiflorus.

[occidentalis]

Sasha brings up the subject of L. grandiflorus and MDMA early in the lecture and specifically notes a “peak of a trace component of MDMA” in L. grandiflorus and goes on to mention that it has the “same empirical formula...as MDMA.” But he clearly says about this “trace component” that if you “put the methyl group off the nitrogen and stuck it on the alpha position you’d have MDMA, same mass spectrometry.” This clearly indicates that MDMA is not in the cactus, but only that a closely related property is present that with some minor tweaking can be altered to MDMA. Not being a chemist myself, or one who even has a particular interest in it, and not knowing the lingo particularly well, I do understand that a “trace component of MDMA” doesn’t mean MDMA. The significance of “empirical formula” is not well understood by me, but I’m curious if in technical terms it indicates a broader grouping of chemicals rather than just one specific alkaloid.

This means the compound was N-MMDP. An analogous difference would be between N-MT and AMT. The methyl is just in a slightly different place, but this would make a big difference pharmacologically. It still isn't technically correct to say it was a trace amount of MDMA, because it wasn't MDMA. I guess it looked the same on the mass spec, and Sasha is used to looking for MDMA on mass spec results, so he saw MDMA even thought it wasn't technically.

The empirical formula is just the sum of the elements - so how many Cs, how many Ns, how many Os, how many Hs. In this case the empirical formula would be the same, because both these compounds contain the same number of atoms of the same elements.

[mark80]

The empirical formula is just the sum of the elements - so how many Cs, how many Ns, how many Os, how many Hs. In this case the empirical formula would be the same, because both these compounds contain the same number of atoms of the same elements.

Becuase psychoactives are usally very big molecules having the smae emirial formlula doesn't mean squat as they could be arrangeed differntly. The picture below (yes my paint skills are very good ) shows the same empirical formula but a diffenrt structure.

[teonanacatl]

nature can synthesise methylenedioxy groups and also the basic amphetamine structure eg ephedrine so I see no reason it could not synthesise MDMA. I remember listening to the talk online and never thought much of those comments about MDMA in cacti, still dont really as there is alot more to it no doubt.

[M S Smith]

Hey teonanacatl, I wasn't out to argue against the possibility of the natural production of MDMA, but rather just wanted to clear up the misunderstanding of it having been found in T. grandiflorus as drawn from Shugin's "Cacti".

~Michael~

[Teotzlcoatl]

So this cactus doesn't contain MDMA....but could it still has psychoactive properties?

Has anybody ever bioassyed it?

Lobivia grandiflorus = Trichocereus grandiflorus???

[trucha]

Its an error to try and view the assorted grandifloras as synonyms since a morass exists there which includes hybrids.

Merging Trichocereus, Lobivia and Echinopsis caused a serious mess that seems unlikely to ever be untangled as regards this name.

The last I saw concerning the grandiflora/grandiflorus (from Hunt) the Lobivia had become Echinopsis rowleyii, the Echinopsis had been abandoned as invalid, despite it being considered a possible synonym of Echinopsis calochlora in his previous book, and the Trichocereus had become Echinopsis huascha despite Hunt thinking the Lobvia was also this in his previous book. Expect more alterations.

Creach put it best in saying why Sasha did not say there was bona fide MDMA in the one he tested.

The odd molecule he DID think he observed did not appear to be in other forms called grandiflora.

I was at that talk and never took it to mean he actually found MDMA.

I've never seen any result from him suggesting it was observed in pachycereus. Am I missing something?

[M S Smith]

kt, he didn't make a comment about finding MDMA in Pachycereus (though he had addressed this plant otherwise), he rather when talking about MDMA in the "grandiflorus" makes a mistake in its location, confusing it with the location of Pachycereus. He states how could it be that he might “find a little bit of MDMA in a cacti that grows in Baja, California, and halfway down the peninsula?” Just a "brain fart" as he so kindly calls it.

~Michael~