3-Methoxy-4-methylamphetamine
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Clinical data | |
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Routes of administration |
Oral |
ATC code | none |
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CAS Number | 87179-33-7 ![]() |
PubChem (CID) | 91253 |
ChemSpider | 82402 ![]() |
ChEMBL | CHEMBL47696 ![]() |
Chemical and physical data | |
Formula | C11H17NO |
Molar mass | 179.258 g/mol |
3D model (Jmol) | Interactive image |
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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 (decade).[4][unreliable source?]
In animal studies, MMA fully substitutes for MDMA and MBDB, partially substitutes for LSD, and does not substitute for amphetamine.[2] Additionally, it has been shown to potently inhibit the reuptake of serotonin and does not produce serotonergic neurotoxicity in rodents.[2] These data appear to confer a profile of MMA as a selective serotonin releasing agent (SSRA) and 5-HT2A receptor agonist.[2]
At high doses, such as 120 mg, the effects are psychedelic (comparable to DOM).[5]
See also[edit]
- 3-Methoxyamphetamine (3-MeOA)
- 3-Methoxymethamphetamine (MMMA)
- 4-Methylamphetamine (4-MA)
- 4-Methylmethamphetamine (4-MMA)
- 4-Methylmethcathinone (4-MMC)
References[edit]
- ^ a b 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.
- ^ a b c d e 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.
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Miscellaneous |
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- Drugs with non-standard legal status
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