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3-Methyl-4,5-methylenedioxyamphetamine
Systematic (IUPAC) name
1-(7-methyl-1,3-benzodioxol-5-yl)propan-2-amine
Identifiers
CAS number 749191-14-8
204916-89-2 (hydrochloride)
ATC code  ?
PubChem 10012829
Chemical data
Formula C 11H15NO2  
Mol. mass 193.242 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes  ?

3-Methyl-4,5-methylenedioxyamphetamine (5-Methyl-MDA) is a ring-methylated derivative of the entactogenic 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] More recent research has used these animal activity results of the effects of ring-methylation to help guide computer modeling of the serotonin transporter complex.[3] Anecdotal reports from human users suggest that 5-methyl-MDA produces MDMA-like effects but is several times more potent by weight, and with mainly stimulant and less empathogenic effects.

See also

  • 2-Methyl-MDA
  • 6-Methyl-MDA

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
  3. ^ Walline CC, Nichols DE, Carroll FI, Barker EL. Comparative molecular field analysis using selectivity fields reveals residues in the third transmembrane helix of the serotonin transporter associated with substrate and antagonist recognition. Journal of Pharmacology and Experimental Therapeutics. 2008 Jun;325(3):791-800. PMID 18354055







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