3-Methoxy-4-methylamphetamine

3-Methoxy-4-methylamphetamine

Systematic (IUPAC) name
1-(3-methoxy-4-methylphenyl)propan-2-amine
Clinical data
Legal status	UK: Class A US: Uncontrolled (but may be covered under the Federal Analog Act in the United States and under similar bills in other countries)
Routes of administration	Oral
Identifiers
CAS Number	87179-33-7 N
ATC code	none
PubChem	CID: 91253
ChemSpider	82402 Y
ChEMBL	CHEMBL47696 Y
Chemical data
Formula	C11H17NO
Molecular mass	179.258 g/mol
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)

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

In animal studies, MMA fully substitutes for MDMA and MBDB, partially substitutes for LSD, and does not substitute for amphetamine. Additionally, it has been shown to potently inhibit the reuptake of serotonin and does not produce serotonergic neurotoxicity in rodents. These data appear to confer a profile of MMA as a selective serotonin releasing agent (SSRA) and 5-HT_2A receptor agonist.

At high doses, such as 120 mg, the effects are psychedelic (comparable to DOM).

See also

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