3-Methoxy-4-methylamphetamine

Entactogen and psychedelic drug of the phenethylamine and amphetamine classes From Wikipedia, the free encyclopedia

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.[citation needed]

Routes of
administrationOral
ATC code
  • None
Legal status
CAS Number
Quick facts Clinical data, Routes ofadministration ...
MMA
Clinical data
Routes of
administration		Oral
ATC code
  • None
Legal status
Legal status
Identifiers
  • 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)
  • COc1cc(CC(N)C)ccc1C
  • 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 checkY
  • Key:XDXMRSBXBOXSQW-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)
Close

In animal studies, MMA fully substitutes for MDMA and MBDB, partially substitutes for LSD, and does not substitute for amphetamine in rodent drug discrimination tests.[2] However, in another study, MMA fully substituted for dextroamphetamine in such tests.[4] Additionally, it has been shown to be a potent and highly selective serotonin releasing agent (SSRA) and does not produce serotonergic neurotoxicity in rodents.[5][2][6] These data appear to confer a profile of MMA as a selective serotonin releasing agent (SSRA) and serotonin 5-HT2A receptor agonist.[2]

In humans, MMA has been reported to be hallucinogenic, "quite dypshoric", and long-lasting.[7] The active doses have been reported to be 40 to 60 mg.[7] Capsules containing 140 mg have been encountered as a designer drug in Italy in the 1980s.[7]

The 2-aminoindane analogue of MMA is 5-methoxy-6-methyl-2-aminoindane (MMAI).[8][6]

See also

References

Related Articles

Wikiwand AI