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ARCHIVE:  September 26, 2001

Acacias and Natural Amphetamine

Dear Dr. Shulgin:

Are you familiar with Acacia berlandieri and A. rigidula which were noted to contain various a-methyl-b-phenethylamines? Do you have any ideas as to what the botanical origins of these structural carbon skeletons might be? The literature citations are PHYTOCHEM. (1998), 49(5), 1377 and PHYTOCHEM. (1997), 46(2), 249. 

-- Auto

Dear Auto:

I am familiar with the literature concerning these two West Texas Acacia species, but not with the plants themselves. I had both these PHYTOCHEMISTRY papers in my Acacia file but I must admit that I have some very mixed feelings about them.  

What caught my curiosity immediately was the casual indifference shown to what is certainly an extraordinary discovery. Here, amongst some 40 or so alkaloids found in each of these two species, there were five amphetamines that had heretofore been thought to be inventions of man. Two of these are Schedule II drugs, Amphetamine and Methamphetamine. Two are Schedule I drugs, N,N-Dimethylamphetamine and 4-Methoxyamphetamine. And the fifth one is a major human metabolite of Amphetamine, 4-Hydroxyamphetamine. To my knowledge, none of these had ever before been reported as being natural plant alkaloids. This unprecedented discovery elicited only a passing line of comment in the earlier of the two papers.

My first thoughts as to origin were directed towards the well known natural hydroxylated amphetamines such as norephedrine, ephedrine and N-methylephedrine. I know that ephedrine and pseudoephedrine, frequent precursors in the illegal synthesis of methamphetamine, can be reduced to methamphetamine as an artifact of analysis. The sample insertion conditions of the gas chromatograph can effect this conversion. But then, there was no mention of any of these hydroxylated alkaloids as being present in either Acacia.

Might a contaminated round-bottomed flask have been purchased at a garage sale outside an abandoned meth-lab and served as the source of these "man-made" compounds? Unlikely, even in Texas.

Even more dramatic, one of these amphetamines, the 4-Methoxyamphetamine, is the increasingly notorious PMA that is appearing as one of the lethal "Ecstasy" offerings in the rave scene.

Several months ago I tried to contact, individually, the two principal authors, by both e-mail and personal snail-mail, and I have received no response as yet.

There is certainly precedent for a drug which was originally man-made, to be discovered in a plant. N,N-Dimethyltryptamine (DMT) was first synthesized by Manske, in Canada, in the 1930s. It was over twenty years later that it was discovered in a plant from South America. But such an event usually evokes considerable commentary. Here it seems that an exciting story is being ignored. Am I missing something?

-- Dr. Shulgin

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