Amiflamine

Amiflamine
Clinical data
Other names	FLA-336; (S)-2-Methyl-4-(dimethylamino)amphetamine
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 (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.