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ARCHIVE: April 24, 2003
MDMA Variations & Freedom of Inquiry
Dear Dr. Shulgin:
Do you now if there are any variations of MDMA where there is a reaction of something, a nitrogen, an N-methyl group, the alpha-methyl group, back upon the aromatic system to form a new ring? This would be sort of a phenethylamine version of the tail end of the tryptamine chain reacting back upon its aromatic system to form the harmine/harmaline compounds. --Adam
In the actual chain cyclization of a bicyclic tryptamine to form a tricyclic harmaline or tetrahydraharmine compound, there is always the intervention of a separate source of a carbon atom or carbon atoms to provide the stuff to make that new ring a six membered one. The analogy with the phenethylamines would produce isoquinolines. There are a lot of these alkaloids in the plant world and a number of them are biologically active. The actual two ring products that would come from the cyclization of an amphetamine (such as MDMA) are very rare: They would have that chain methyl group sticking out of the newly formed ring at a most unnatural place. But the products from the corresponding phenethylamines (with no chain methyl group) do exist, although they have not been much studied.
There is a rich variation of what you are searching for, where there is the introduction of a carbon atom (as with the harmaline analogy) between the methyl group and the aromatic ring, leaving the amine group attached to the new ring, but not a part of it. These are called the aminotetralines. And if the extra carbon atom is not invoked, there will be a five member ring formed and these cycles are called aminoindanes. And the amine group can be the primary amine -NH2 or the N-methylamine, -NHCH3.
There has been a lot of study with the methylenedioxy substituted amino tetralines and indanes, and there is quite a bit of interesting pharmacology reported. Studies at the University of Virginia in Richmond, have reported stimulant properties. At Purdue, in Indiana, these compounds were tried in two studies, one with a group of rats trained to distinguish LSD from saline, and the other to distinguish MDMA from saline. None of the compounds assays substituted for LSD, but several did substitute quite well for MDMA with the appropriately trained groups. In acute trials, both the methylenedioxyaminotetraline and the methylendioxyaminoindane showed MDMA-like behavior but with none of the serotonin neurotoxicity associate with MDMA use.
But this is all in the rat. It would be nice if the National Institute of Mental Health might someday fund a grant to explore these reasonably non-toxic compounds in human subjects. It would be nice if the authorities would simply give its permission for these clinical studies to be made with human subjects. If the scientific research area were today what it was a hundred years ago, and you accepted the responsibility for such studies and funded them yourself, there was no meaning to asking for permission. You ask yourself a scientific question. You get an experimental answer. You publish your question and answer in a professional journal. But that was a hundred years ago, and I personally do not believe that the aura of that time, as to personal honesty and integrity, will ever be recovered. It is a sad loss of a very subtle freedom. The freedom of inquiry.
-- Dr. Shulgin
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