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ARCHIVE: June 3, 2004
Dear Dr. Shulgin:
I was wondering if you have ever come across the cathinone family of drugs in your research? I was wondering, because cathinone is very similar in structure to the amphetamines. Is there a way of synthesizing different types of cathinones from starting amphetamines? One only has to oxidase ephedrine to create methcathinone which I have tried and enjoyed thoroughly. Might this open up a new family of stimulant drug? -- Phil
There is a close similarity of structure of the three pharmacologically active compounds, methamphetamine, ephedrine and methcathinone. In fact, except for the degree of oxidation on the beta-carbon atom, they are identical. Methamphetamine has two hydrogens there (H,H), ephedrine has a hydroxyl group there (H,OH) and methcathinone has a ketone group there (=O).
Ephedrine can be reduced to methamphetamine in a number of ways, and in fact this is currently the most popular illegal process for making it. It can be oxidized easily to give methcathinone, but I know of no process that can go directly from an amphetamine to a cathinone.
I have long speculated that maybe some of these conversions might take place enzymatically in the brain. It is difficult for most polar compounds to cross the lipophilic Blood Brain Barrier (the BBB) and that hydroxy group in ephedrine (H,OH) is pretty polar. So maybe methamphetamine (not very polar) can get into the brain, and be oxidized there. Similarly, methcathinone (also not very polar) can get into the brain, and be reduced there. The product of both reactions would be ephedrine, and so it may be the sole active principle for both of these stimulants but it is metabolically created within the brain. Following this hypothetical pathway, I wondered if 3,4-methylenedioxymethamphetamine (MDMA) might actually be converted to the ephedrine analog in the brain (H,H to H,OH), and that this metabolite might be the actual active drug.
Carrying this argument one step further, the obvious challenge would be to see just how the cathinone counterpart of MDMA (3,4-
methylenedioxymethcathinone) might compare in activity to MDMA. If it were to cross the BBB and be reduced to that hypothetical ephedrine analog (=O to H,OH) it might have the same potency and psychopharmacology as MDMA. So I made the compound (I called it Methylone) and by golly it has almost the same potency, but it doesn't produce the same effects. It has an almost antidepressant action, pleasant and positive, but not the unique magic of MDMA. Its properties will be given in detail in Ann's and my third book, which should be out in a couple of years.
-- Dr. Shulgin
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