3-Methoxy-4-methylamphetamine

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3-Methoxy-4-methylamphetamine
3-Methoxy-4-methylamphetamine.png
Systematic (IUPAC) name
1-(3-methoxy-4-methylphenyl)propan-2-amine
Clinical data
Legal status Uncontrolled (but may be covered under the Federal Analog Act in the United States and under similar bills in other countries)
Routes Oral
Identifiers
CAS number 87179-33-7 N
ATC code None
PubChem CID 91253
ChemSpider 82402 YesY
ChEMBL CHEMBL47696 YesY
Chemical data
Formula C11H17NO 
Mol. mass 179.258 g/mol
 N (what is this?)  (verify)

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) but can be dysphoric and very long-lived.[5]

See also[edit]

References[edit]

  1. ^ 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. 
  2. ^ 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. 
  3. ^ de Zorzi C, Cavalli A, Un nuovo allucinogeno: la MMA (p-metil-m-metossi anfetamina) Zacchia. 1974;49 (1) p.58-68
  4. ^ "Bluelight Forums - MMA - 3-MeO-4-Me-Amphetamine". 
  5. ^ Ann Shulgin; Alexander Shulgin (1991). Pihkal: A Chemical Love Story. Transform Press. ISBN 0-9630096-0-5.