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).
|Chemical and physical data|
|Molar mass||179.258 g/mol g·mol−1|
|3D model (JSmol)|
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-HT2A receptor agonist.
At high doses, such as 120 mg, the effects are psychedelic (comparable to DOM).
- Ho BT, McIsaac WM, An R, et al. (January 1970). "Analogs of alpha-methylphenethylamine (amphetamine). I. Synthesis and pharmacological activity of some methoxy and/or methyl analogs". Journal of Medicinal Chemistry. 13 (1): 26–30. doi:10.1021/jm00295a007. PMID 5412110.
- Johnson MP, Frescas SP, Oberlender R, Nichols DE (May 1991). "Synthesis and pharmacological examination of 1-(3-methoxy-4-methylphenyl)-2-aminopropane and 5-methoxy-6-methyl-2-aminoindan: similarities to 3,4-(methylenedioxy)methamphetamine (MDMA)". Journal of Medicinal Chemistry. 34 (5): 1662–8. doi:10.1021/jm00109a020. PMID 1674539.
- de Zorzi C, Cavalli A, Un nuovo allucinogeno: la MMA (p-metil-m-metossi anfetamina) Zacchia. 1974;49 (1) p.58-68
- "Bluelight Forums – MMA – 3-MeO-4-Me-Amphetamine".
- Ann Shulgin; Alexander Shulgin (1991). Pihkal: A Chemical Love Story. Transform Press. ISBN 0-9630096-0-5.
See also: Receptor/signaling modulators • Monoamine reuptake inhibitors • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins
(and close relatives)