Structure via PubChem · Public domain (PubChem)
3-methoxy-4-methylamphetamine
Sign in to save3-Methoxy-4-methylamphetamine (MMA) is an entactogen and psychedelic drug of the phenethylamine and amphetamine classes. It was first synthesized in 1970 and was encountered as a street drug in Italy in the same decade. MMA was largely forgotten until being reassayed by David E. Nichols as a non-neurotoxic MDMA analogue in 1991, and has subsequently been sold as a designer drug on the internet since the late 2000s.
In the Vinony graph
Vinony's link graph records 1,799 inbound references to 3-methoxy-4-methylamphetamine, and connects out to 2C-G, tryptamines and 3,4-methylenedioxy-N-hydroxy-N-methylamphetamine.
It sits within the topics Chemical pages without DrugBank identifier, David E. Nichols and Designer drugs.
Vinony links it to 5 Wikipedia language editions.
Chemical data
- Formula
- C11H17NO
- Molecular weight
- 179.26 g/mol
- IUPAC name
- 1-(3-methoxy-4-methylphenyl)propan-2-amine
- SMILES
- CC1=C(C=C(C=C1)CC(C)N)OC
- InChIKey
- XDXMRSBXBOXSQW-UHFFFAOYSA-N
- XLogP
- 2
- Polar surface area
- 35.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Has part
- carbon
- Mass
- 179.131014
Show 4 more facts
- chemical formula
- C₁₁H₁₇NO
- canonical SMILES
- CC1=C(C=C(C=C1)CC(C)N)OC
- density
- 0.979
- boiling point
- 271.766
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
3-Methoxy-4-methylamphetamine (MMA) is an entactogen and psychedelic drug of the phenethylamine and amphetamine classes. It was first synthesized in 1970 and was encountered as a street drug in Italy in the same decade. MMA was largely forgotten until being reassayed by David E. Nichols as a non-neurotoxic MDMA analogue in 1991, and has subsequently been sold as a designer drug on the internet since the late 2000s.
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. However, in another study, MMA fully substituted for dextroamphetamine in such tests. Additionally, it has been shown to be a potent and highly selective serotonin releasing agent (SSRA) and does not produce serotonergic neurotoxicity in rodents. These data appear to confer a profile of MMA as a selective serotonin releasing agent (SSRA) and serotonin 5-HT2A receptor agonist.
Excerpted from Wikipedia’s “3-methoxy-4-methylamphetamine” article, available under the CC BY-SA 4.0 licence.