3-Methyl-4,5-methylenedioxyamphetamine

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3-Methyl-4,5-methylenedioxyamphetamine
Systematic (IUPAC) name
1-(7-methyl-1,3-benzodioxol-5-yl)propan-2-amine
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PubChem 10012829
Chemical data
Formula C11H15NO2 
Mol. mass 193.242 g/mol
SMILES eMolecules & PubChem
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3-Methyl-4,5-methylenedioxyamphetamine or 5-Methyl-MDA is a ring-methylated derivative of the empathogenic drug MDA and a structural isomer of MDMA. It substitutes for MDA in animal tests and in vivo testing showed that 5-methyl-MDA is both several times more potent and much more selective as a releaser of serotonin over the other monoamines dopamine and noradrenaline compared to MDA itself. The other isomer 2-methyl-MDA is also more potent than MDA, although less potent than 5-methyl-MDA,[1] but both 6-methyl-MDA and the 6-methyl derivative of MDMA, Madam-6, are inactive, most likely due to steric hindrance.[2] Anecdotal reports from human users suggest that 5-methyl-MDA produces MDMA-like effects but is several times more potent by weight.


[edit] References

  1. ^ Parker MA, Marona-Lewicka D, Kurrasch D, Shulgin AT, Nichols DE. Synthesis and pharmacological evaluation of ring-methylated derivatives of 3,4-(methylenedioxy)amphetamine (MDA). Journal of Medicinal Chemistry. 1998 Mar 12;41(6):1001-5. PMID 9526575
  2. ^ PIHKAL #98