Structure via PubChem · Public domain (PubChem)
amiflamine
Sign in to saveAlso known as FLA-336
Amiflamine (developmental code name FLA-336), also known '(S)-2-methyl-4-(dimethylamino)amphetamine', is a reversible inhibitor of monoamine oxidase A (MAO-A), thereby being a RIMA, and, to a lesser extent, semicarbazide-sensitive amine oxidase (SSAO) inhibitor, as well as a serotonin releasing agent (SRA). It is a derivative of the phenethylamine and amphetamine families. The (+)-enantiomer is the active stereoisomer.
Chemical data
- Formula
- C12H20N2
- Molecular weight
- 192.3 g/mol
- IUPAC name
- 4-[(2S)-2-aminopropyl]-N,N,3-trimethylaniline
- SMILES
- CC1=C(C=CC(=C1)N(C)C)C[C@H](C)N
- InChIKey
- HFQMYSHATTXRTC-JTQLQIEISA-N
- XLogP
- 2.2
- Polar surface area
- 29.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
51 papers- Relationship of N-demethylation of amiflamine and its metabolite to debrisoquine hydroxylation polymorphism.Clinical pharmacology and therapeutics · 1984
- Pressor response of oral tyramine in healthy men given amiflamine and placebo.Clinical pharmacology and therapeutics · 1986
- Selective inhibition by amiflamine of monoamine oxidase type A in rat brain, liver and duodenum.Naunyn-Schmiedeberg's archives of pharmacology · 1984
- Effects of amiflamine and related compounds on the accumulation of biogenic monoamines in rat brain slices in vitro and ex vivo in relation to their behavioural effects.Acta pharmacologica et toxicologica · 1985
- Effect of repeated amiflamine administration on serotonergic and noradrenergic neurotransmission: electrophysiological studies in the rat CNS.Naunyn-Schmiedeberg's archives of pharmacology · 1986
via PubMed
Wikidata facts
- Mass
- 192.16264864
Show 5 more facts
- chemical formula
- C₁₂H₂₀N₂
- canonical SMILES
- CC1=C(C=CC(=C1)N(C)C)CC(C)N
- World Health Organisation international non-proprietary name
- amiflaminum
- subject has role
- monoamine oxidase inhibitor
- isomeric SMILES
- Cc1cc(ccc1C[C@H](C)N)N(C)C
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- See also
- References
- External links
Amiflamine (developmental code name FLA-336), also known '(S)-2-methyl-4-(dimethylamino)amphetamine', is a reversible inhibitor of monoamine oxidase A (MAO-A), thereby being a RIMA, and, to a lesser extent, semicarbazide-sensitive amine oxidase (SSAO) inhibitor, as well as a serotonin releasing agent (SRA). It is a derivative of the phenethylamine and amphetamine families. The (+)-enantiomer is the active stereoisomer.
Amiflamine shows preference for inhibiting MAO-A in serotonergic relative to noradrenergic and dopaminergic neurons. In other words, at low doses, it can be used to selectively inhibit MAO-A enzymes in serotonin cells, whereas at higher doses it loses its selectivity. This property is attributed to amiflamine's higher affinity for the serotonin transporter over the norepinephrine and dopamine transporters, as transporter-mediated carriage is required for amiflamine to enter monoaminergic neurons.
Excerpted from Wikipedia’s “amiflamine” article, available under the CC BY-SA 4.0 licence.