Amiflamine

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

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 Y
PubChem CID	71221
ChemSpider	64356 Y
UNII	NE25WV9C8S
ChEMBL	ChEMBL30344 N
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 Y Key:HFQMYSHATTXRTC-JTQLQIEISA-N Y
NY (what is this?)  (verify)

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]

See also

• Reversible inhibitor of MAO-A (RIMA)
• Monoamine oxidase inhibitor (MAOI)