Amiflamine

Amiflamine
Clinical data
Other names	(+)-4-(dimethylamino)-α,2-dimethylphenethylamine
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	In general: uncontrolled;
Identifiers
	IUPAC name 4-[(2S)-2-Aminopropyl]-N,N,3-trimethylaniline;
CAS Number	77518-07-1 ;
PubChem CID	71221;
ChemSpider	64356 ;
UNII	NE25WV9C8S;
ChEMBL	ChEMBL30344 ;
CompTox Dashboard (EPA)	DTXSID00228222 ;
Chemical and physical data
Formula	C12H20N2
Molar mass	192.306 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES N(c1cc(c(cc1)C[C@@H](N)C)C)(C)C;
	InChI InChI=1S/C12H20N2/c1-9-7-12(14(3)4)6-5-11(9)8-10(2)13/h5-7,10H,8,13H2,1-4H3/t10-/m0/s1 ; Key:HFQMYSHATTXRTC-JTQLQIEISA-N ;
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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 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]

References

^ ^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.
^ ^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. S2CID 25342831.
^ 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.
^ 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. S2CID 21817180.
^ ^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.
^ ^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. S2CID 403633.