3-Methoxy-4-methylamphetamine

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).

3-Methoxy-4-methylamphetamine
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
  • US: Uncontrolled (but may be covered under the Federal Analog Act in the United States and under similar bills in other countries)
Identifiers
IUPAC name
  • 1-(3-methoxy-4-methylphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H17NO
Molar mass179.263 g·mol−1
3D model (JSmol)
SMILES
  • COc1cc(CC(N)C)ccc1C
InChI
  • InChI=1S/C11H17NO/c1-8-4-5-10(6-9(2)12)7-11(8)13-3/h4-5,7,9H,6,12H2,1-3H3 Y
  • Key:XDXMRSBXBOXSQW-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

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).[4]

See also

References
  1. Ho BT, McIsaac WM, An R, Tansey LW, Walker KE, Englert LF, Noel MB (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. 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. Shulgin A, Shulgin A (1991). Pihkal: A Chemical Love Story. Transform Press. ISBN 0-9630096-0-5.
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