Amiflamine

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Amiflamine
Amiflamine.svg
Systematic (IUPAC) name
4-[(2S)-2-aminopropyl]-N,N,3-trimethylaniline
Clinical data
Legal status
  • Uncontrolled
Routes Oral
Identifiers
CAS number 77518-07-1 YesY
ATC code None
PubChem CID 71221
ChemSpider 64356 YesY
UNII NE25WV9C8S YesY
ChEMBL CHEMBL30344 N
Synonyms (+)-4-(dimethylamino)-α,2-dimethylphenethylamine
Chemical data
Formula C12H20N2 
Molecular mass 192.30 g/mol
 N (what is this?)  (verify)

Amiflamine (FLA-336) is a reversible inhibitor of monoamine oxidase A (MAO-A), thereby being a RIMA, and, to a lesser extent, semicarbazide-sensitive amine oxidase (SSAO), as well as a serotonin releasing agent (SRA).[1][2][3][4] It is a derivative of the phenethylamine and amphetamine chemical classes.[1] The (+)-enantiomer is the active stereoisomer.[2]

Amiflamine is unique among MAOIs in that it shows preference for inhibiting MAO-A in serotonergic relative to noradrenergic and dopaminergic neurons.[5][6] 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.[5][6] 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.[6]

See also[edit]

References[edit]

  1. ^ a b Ask AL, Högberg K, Schmidt L, Kiessling H, Ross SB (April 1982). "(+)-4-Dimethylamino-2,alpha-dimethylphenethylamine (FLA 336(+)), a selective inhibitor of the A form of monoamine oxidase in the rat brain". Biochemical Pharmacology 31 (7): 1401–6. doi:10.1016/0006-2952(82)90035-1. PMID 7092929. 
  2. ^ a b Fowler CJ, Eriksson M, Thorell G, Magnusson O (October 1984). "Stereoselective inhibition of monoamine oxidase and semicarbazide-sensitive amine oxidase by 4-dimethylamino-2,alpha-dimethylphenethylamine (FLA 336)". Naunyn-Schmiedeberg's Archives of Pharmacology 327 (4): 279–84. doi:10.1007/bf00506237. PMID 6514012. 
  3. ^ Morikawa F, Ueda T, Arai Y, Kinemuchi H (1986). "Inhibition of monoamine oxidase A-form and semicarbazide-sensitive amine oxidase by selective and reversible monoamine oxidase-A inhibitors, amiflamine and FLA 788(+)". Pharmacology 32 (1): 38–45. doi:10.1159/000138150. PMID 3945672. 
  4. ^ Ask AL, Fagervall I, Huang RB, Ross SB (June 1989). "Release of 3H-5-hydroxytryptamine by amiflamine and related phenylalkylamines from rat occipital cortex slices". Naunyn-Schmiedeberg's Archives of Pharmacology 339 (6): 684–9. doi:10.1007/bf00168662. PMID 2770890. 
  5. ^ a b Fowler CJ, Magnusson O, Ross SB (1984). "Intra- and extraneuronal monoamine oxidase". Blood Vessels 21 (3): 126–31. doi:10.1159/000158505. PMID 6202347. 
  6. ^ a b c Ask AL, Fagervall I, Ross SB (September 1983). "Selective inhibition of monoamine oxidase in monoaminergic neurons in the rat brain". Naunyn-Schmiedeberg's Archives of Pharmacology 324 (2): 79–87. doi:10.1007/BF00497011. PMID 6646243.