5-Methyl-MDA

5-Methyl-MDA

Systematic (IUPAC) name
1-(7-methyl-1,3-benzodioxol-5-yl)propan-2-amine
Clinical data
Legal status	Schedule I (as it is an isomer of MDMA, it is covered under Federal Analogue Act in the United States)
Routes of administration	Oral
Identifiers
CAS Number	749191-14-8 N 204916-89-2 (HCl)
ATC code	none
PubChem	CID: 10012829
ChemSpider	8188403 Y
ChEMBL	CHEMBL6330 Y
Chemical data
Formula	C11H15NO2
Molecular mass	193.242 g/mol
SMILES O2COc1c2cc(CC(N)C)cc1C
InChI InChI=1S/C11H15NO2/c1-7-3-9(4-8(2)12)5-10-11(7)14-6-13-10/h3,5,8H,4,6,12H2,1-2H3 Y Key:OLENSVFSNAULML-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

5-Methyl-3,4-methylenedioxyamphetamine (5-Methyl-MDA) is an entactogen and psychedelic drug of the amphetamine class. It is a ring-methylated derivative of MDA and a structural isomer of MDMA. Drug discrimination studies showed that 5-methyl-MDA substitutes for MDA, MMAI, and LSD, but not amphetamine, suggesting that it produces a mix of entactogen and hallucinogenic effects without any stimulant effects.

5-Methyl-MDA acts as a selective serotonin releasing agent (SSRA) with IC₅₀ values of 107nM, 11,600nM, and 1,494nM for serotonin, dopamine, and norepinephrine efflux. It is over 5x more potent than MDA, with a suitable active dose possibly being around 15–25 mg. Subsequent testing, however, has found that it is not as potent as once thought and is active at at least 100mg. 2-Methyl-MDA is also much more potent than MDA, but is not quite as potent as 5-methyl-MDA. 6-methyl-MDMA (also known as Madam-6) is mostly inactive, likely due to steric hindrance.

Recent research has used data on 2-methyl-MDA and 5-methyl-MDA to help guide computer modeling of the serotonin transporter complex.

The synthesis of 5-methyl-MDA can be found online.

See also

• 2-Methyl-MDA
• 6-Methyl-MDA
• EDA
• MMDA