MMDA-5, also known as 6-methoxy-2,3-methylenedioxyamphetamine or as 6-methoxy-ORTHO-MDA, is a psychoactive drug of the phenethylamine, amphetamine, and MDxx families related to ORTHO-MDA (2,3-MDA). "The remaining MMDA-analogue that has been prepared, is the 2,3,6-isomer. The flow diagram started with sesamol (3,4-methylenedioxyphenol) which was methylated with methyl iodide, converted to the aldehyde using butyllithium and N-methylformanilide (putting the new group directly between the two oxygen atoms, giving 2,3-methylenedioxy-6-methoxybenzaldehyde), reaction with nitroethane to the nitrostyrene, and its reduction with lithium aluminum hydride in ether. The product, 6-methoxy-2,3-methylenedioxyamphetamine hydrochloride (MMDA-5) is practically unexplored in man. I have heard one report that 30 milligrams was modestly active, but not a particularly pleasant experience. Another person told me that he had tried 15 milligrams, but he neglected to mention if there had been any effects. I have not tried it myself. But, I have succumbed to the pressure of the experimental pharmacologists to give a number for the “Y-axis” of their animal behavior studies. So I said to myself, if this is active at 30 milligrams, and mescaline is active at 300 milligrams, why not say that it is 10× the activity of mescaline? So I did. But I have absolutely no confidence in that number." It is the 6-methoxy derivative of ORTHO-MDA and is a positional isomer of MMDA-2 (6-MeO-3,4-MDA) and related compounds like MMDA (5-MeO-3,4-MDA) and MMDA-3a (2-MeO-3,4-MDA).
Alexander Shulgin briefly mentions MMDA-5 in his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications. According to Shulgin, MMDA-5 has been very sparsely explored in humans. In any case, he described two experience reports with it that had been communicated to him. The first, at 30mg orally, was said to be modestly active but not a particularly pleasant experience, whereas the other was at 15mg orally but whether there were any effects was not mentioned. Shulgin did not test MMDA-5 himself, and the effects of MMDA-5, for instance whether it produces hallucinogenic or stimulant effects, have not otherwise been described. Based on the 30mg report, Shulgin concluded that MMDA-5 might have approximately 10 or 12times the potency of mescaline.
The chemical synthesis of MMDA-5 has been described. Other 2,3-MDA positional isomers of MMDA-5 include MMDA-3b and MMDA-4.
MMDA-5 was first described in the scientific literature by Shulgin and colleagues in 1969. Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.
See also Substituted methylenedioxyphenethylamine Methoxymethylenedioxyamphetamine (MMDA)
References
External links MMDA-5 - Isomer Design