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ARCHIVE:  June 3, 2003

MDMA and its Methylenedioxy Ring

Dear Dr. Shulgin:

Has there been any success seen with the adding of alkyl groups to the methylenedioxy carbon of MDMA? --Anon

Dear Anon:

To a simple question, there is a simple answer. No. But the question is intrinsically quite complex. What is being asked, in a general hand-waving sense, is whether there any change in psychopharmacologically potency resulting from mucking around with the methylenedioxy group of MDMA. Or, in other words, must that group remain intact to maintain the magical activity of MDMA? My laboratory syntheses of explicit compounds to address this question has not been very systematic and, in truth, I don't really know. Let me share with you what I have observed.

With the specific compound MDMA, I have made only one modification of the methylenedioxy ring. This was to make it into a six membered ring, a dioxane homologue, which I called EDMA for ethylenedioxymethamphetmaine. With this homologue, I went up to twice the active dosage of MDMA and experienced none of the effects that might have been expected. A completely separate ring expansion to the dioxane homologue was explored with MMDA. The 5-membered methylenedioxy ring was expanded to the six-membered dioxane (3-methoxy-4,5-ethylenedioxyamphetamine, MEDA) which was also inactive at a 200 milligram dose. The chemistry was pursued successful up to the seven member ring, the compound named MTDA for 3-methoxy-4,5- trimethylenedioxyamphetamine was also synthesized, but human trials didn't go up very far. It was not an interesting compound (see PIHKAL, page 761).

But this is a ring expansion of the methylenedioxy group, not the alkylation of the methylenedioxy carbon atom. The only studies that I carried out that actually involved alkylation of the furan ring of the phenethylamines related to the dihydrobenzofurans in the THC area. Here the heterocyclic ring is a one-oxygen furan rather than a two-oxygen dioxolane, but I did put a scatter of alkyl groups on central carbon atom. These were, in essence, cyclic DOM analogues. With one methyl group, the compound was called F-2 (2-M) and is on page 664 of PIHKAL. With two methyl groups, it is F-22, and is on page 667. I have not found the active level of either compound.

This does not answer your question. If I had a graduate student doing research for his Ph.D. degree, I would have him synthesize MDMA with its methylenedioxy group substituted with one methyl group, two methyl groups, one ethyl group, and two ethyl groups. Four compounds in all. And for him to determine their potencies in some kosher way, that isn't a problem. I would give you better than even odds that the potencies of all of them would be less than that of MDMA. But I should warn you. The graduate departments of most universities are rather rigid. We may get the compounds synthesized but probably not be able to determine their potencies. But at least we could publish the chemistry and perform some animal studies.

-- Dr. Shulgin

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