3-Methoxy-4-methylamphetamine

Not to be confused with meta-Methoxyamphetamine.

3-Methoxy-4-methylamphetamine (MMA) is an entactogen and psychedelic drug of the phenethylamine and amphetamine classes.^[1][2] It was first synthesized in 1970^[1] and was encountered as a street drug in Italy in the same decade.^[3] MMA was largely forgotten until being reassayed by David E. Nichols as a non-neurotoxic MDMA analogue in 1991,^[2] and has subsequently been sold as a designer drug on the internet since the late 2000s.^{[citation needed]}

MMA

Clinical data
Routes of administration	Oral
ATC code	none
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) UK: Class A US: Schedule I (isomer of PMMA)
Identifiers
IUPAC name 1-(3-methoxy-4-methylphenyl)propan-2-amine
CAS Number	24160-29-0 Y
PubChem CID	91253
ChemSpider	82402 Y
UNII	BHS67KQE5Q
ChEMBL	ChEMBL47696 Y
CompTox Dashboard (EPA)	DTXSID401007386
Chemical and physical data
Formula	C11H17NO
Molar mass	179.263 g·mol−1
3D model (JSmol)	Interactive image
SMILES COc1cc(CC(N)C)ccc1C
InChI InChI=1S/C11H17NO/c1-8-4-5-10(6-9(2)12)7-11(8)13-3/h4-5,7,9H,6,12H2,1-3H3 Y Key:XDXMRSBXBOXSQW-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

In animal studies, MMA fully substitutes for MDMA and MBDB, partially substitutes for LSD, and does not substitute for amphetamine in rodent drug discrimination tests.^[2] However, in another study, MMA fully substituted for dextroamphetamine in such tests.^[4] Additionally, it has been shown to be a potent and highly selective serotonin releasing agent (SSRA) and does not produce serotonergic neurotoxicity in rodents.^[5][2][6] These data appear to confer a profile of MMA as a selective serotonin releasing agent (SSRA) and serotonin 5-HT_2A receptor agonist.^[2]

In humans, MMA has been reported to be hallucinogenic, "quite dypshoric", and long-lasting.^[7] The active doses have been reported to be 40 to 60 mg.^[7] Capsules containing 140 mg have been encountered as a designer drug in Italy in the 1980s.^[7]

The 2-aminoindane analogue of MMA is 5-methoxy-6-methyl-2-aminoindane (MMAI).^[8][6]

See also

• Substituted methoxyphenethylamine
• 3-Methoxyamphetamine (3-MeOA)
• 3-Methoxymethamphetamine (MMMA)
• 4-Methylamphetamine (4-MA)
• 4-Methylmethamphetamine (4-MMA)
• 4-Methylmethcathinone (4-MMC)
• 4-Cl-3-MMC