3-Methoxy-4-methylamphetamine
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3-Methoxy-4-methylamphetamine
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| Systematic (IUPAC) name | |
| 1-(3-methoxy-4-methylphenyl)propan-2-amine | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | Uncontrolled (but may be covered under the Federal Analogue Act in the United States and under similar bills in other countries) |
| Routes | Oral |
| Identifiers | |
| CAS number | 87179-33-7  |
| ATC code | None |
| PubChem | CID 91253 |
| ChemSpider | 82402 |
| ChEMBL | CHEMBL47696 |
| Chemical data | |
| Formula | C11H17NO |
| Mol. mass | 179.258 g/mol |
| SMILES | eMolecules & PubChem |
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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]
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]
According to anecdotal reports, MMA is active in humans at doses of 20–60 mg and possesses a duration of approximately 12–16 hours.[4] It is said to produce empathy and mild 2C-like psychedelic effects, and although it is mood-lifting, it is not euphoric like MDMA and is more antidepressant-like in comparison.[4] At higher doses, such as 140 mg, the effects are much more psychedelic (comparable to DOM) but can be dysphoric and very long-lived.[5]
See also
- 3-Methoxyamphetamine (3-MeOA)
- 3-Methoxymethamphetamine (MMMA)
- 4-Methylamphetamine (4-MA)
- 4-Methylmethamphetamine (4-MMA)
- 4-Methylmethcathinone (4-MMC)
References
- ^ 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, Zacchia. 1974;10:3.
- ^ a b c "Bluelight Forums - MMA - 3-MeO-4-Me-Amphetamine". http://www.bluelight.ru/vb/showthread.php?t=362771.
- ^ Ann Shulgin; Alexander Shulgin (1991). Pihkal: A Chemical Love Story. Transform Press. ISBN 0-9630096-0-5. http://www.erowid.org/library/books_online/pihkal/pihkal123.shtml.
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