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ARCHIVE:  March 27, 2003

TMA, PMA, PMMA, MDMA, and Effects

Dear Dr. Shulgin:

What is PMA and what are its effects? --Anon

Dear Anon:

PMA is the abbreviation for para-methoxyamphetamine, or 4-methoxyamphetamine, or 4-MA.

Amphetamine itself has been well known and widely used both clinically and recreationally as a stimulant and an anorexic from the 1930s. I remember in the 1940s the use of benzedrine inhalers, which were allegedly for bronchial clearing but in reality were for driving through the night without sleep stops or food stops. Or, for studying through the night before a final.

You had no hunger. You were totally alert. Your pulse and blood pressure was up a bit as well. But there was no psychedelic trip there.

One of the very earliest compounds that I personally explored at some depth was an amphetamine with three methoxy substituents on that normally bare benzene ring. This was 3,4,5-trimethoxyamphetamine which was, quite logically, called TMA. It was first looked at in Canada in the mid-1950s as an agent that could distort stroboscope-induced visual patterns. I published a scientific paper in the British journal Nature in 1961, describing its human actions as being psychedelic, and this effectively defined the direction that my research would go for the next 40 years.

My total concentration was, at that time, directed to changes in substitution groups that might alter or modify the nature of the psychotropic effects that were observed. A few years later, the thought occurred to me that, rather than changing the identity of the groups, why not change the number of the groups. The move from zero to three substituents went from amphetamine to trimethoxyamphetamine, from stimulant to psychedelic. What would be the effect of amphetamine with just one substituent?

In early 1967 I synthesized and began tasting the known compound, 4-methoxyamphetamine, and found that it primarily had psychedelic effects at about 60 milligrams. But there was a second effect that was quite disturbing. There was considerable cardiovascular stimulation as well. Some of the TMA effects were clearly there, but some of the amphetamine effects were coming through as well.

I worked with a psychiatrist in New York who felt that this compound (PMA) might be a metabolic source of 4-hydroxyamphetamine, a known metabolite of amphetamine. Could the problems seen with excessive amphetamine use (he asked me) be due to a single chemical that could come from amphetamine or PMA? He explored PMA on several normal subjects, and was disturbed by the obvious cardiovascular stimulation.

I've wondered why this compound was chosen by some synthetic person or persons out there, to be made available to the "ecstasy" market as a substitute for MDMA. Initially I though it might be a reflection of an early study done at the University of Edinburgh that PMA was the most potent hallucinogen that had been studied, second only to LSD. But that was in rats, not in man.

I now believe the reason is much more practical. For the synthesis of MDA and of MDMA, the favorite starting material is the essential oil Isosafrole. And there has been an intense attempt by the law enforcement authorities to restrict the availability of this chemical. However, a closely related essential oil is Anethole and it is readily available from chemical supply houses at a few dollars a pound, with no apparent restrictions on its sale. And if you are completely set up with all the chemicals, equipment and know-how to make MDA or MDMA and you only lack the starting material, you would convert Anethole directly to PMA and the N-methyl counterpart, PMMA. This latter drug has also been seen recently in the Rave world.

The second half of the question was, what are the effects of PMA? At low levels, a seductive psychotropic buzz. Nice. At slightly higher levels, the clear effects of heart stimulation and blood pressure rise. Not nice. There have been reports of deaths associated with the use of PMA.

I would suggest staying away from this compound.

-- Dr. Shulgin

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