3-Methoxy-4-methylamphetamine
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| Routes of administration | Oral |
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| Formula | C11H17NO |
| Molar mass | 179.263 g·mol−1 |
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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.
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 be a potent and highly selective serotonin releasing agent (SSRA) 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 serotonin 5-HT2A receptor agonist.
In humans, MMA has been reported to be hallucinogenic, "quite dypshoric", and long-lasting. The active doses have been reported to be 40 to 60 mg. Capsules containing 140 mg have been encountered as a designer drug in Italy in the 1980s.
The 2-aminoindane analogue of MMA is 5-methoxy-6-methyl-2-aminoindane (MMAI).