3-Methyl-4,5-methylenedioxyamphetamine
- 3-Methyl-4,5-methylenedioxyamphetamine
Drugbox
IUPAC_name = 1-(7-methyl-1,3-benzodioxol-5-yl)propan-2-amine
width = 200
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PubChem= 10012829
DrugBank=
C=11 | H=15 | N=1 | O=2
molecular_weight = 193.242 g/mol
smiles = O2COc1c2cc(CC(N)C)cc1C
bioavailability=
metabolism =
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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, [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] but both 6-methyl-MDA and the 6-methyl derivative of MDMA, Madam-6, are inactive, most likely due to steric hindrance. [ [http://www.erowid.org/library/books_online/pihkal/pihkal098.shtml PIHKAL #98] ] Anecdotal reports from human users suggest that 5-methyl-MDA produces MDMA-like effects but is several times more potent by weight.
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