Bifemelane

Bifemelane
Clinical data
Trade names	Alnert, Celeport
Other names	MCl-2016, 4-(O-benzylphenoxy)-N-methylbutylamine
AHFS/Drugs.com	International Drug Names
ATC code	N06AX08 (WHO) ;
Identifiers
	IUPAC name N-methyl-4-[2-(phenylmethyl)phenoxy]butan-1-amine;
CAS Number	90293-01-9 ;
PubChem CID	2377;
ChemSpider	2286 ;
UNII	Z4501GN13G;
ChEMBL	ChEMBL1192517 ;
CompTox Dashboard (EPA)	DTXSID1045663 ;
ECHA InfoCard	100.220.566
Chemical and physical data
Formula	C18H23NO
Molar mass	269.388 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O(c1ccccc1Cc2ccccc2)CCCCNC;
	InChI InChI=1S/C18H23NO/c1-19-13-7-8-14-20-18-12-6-5-11-17(18)15-16-9-3-2-4-10-16/h2-6,9-12,19H,7-8,13-15H2,1H3 ; Key:QSQQPMHPCBLLGX-UHFFFAOYSA-N ;
	(what is this?) (verify)

Bifemelane (INN), sold under the brand names Alnert and Celeport, is an antidepressant and cerebral activator that was widely used in the treatment of cerebral infarction patients with depressive symptoms in Japan, and in the treatment of dementia as well. It also appears to be useful in the treatment of glaucoma. It has been discontinued in Japan since 1998, when it was removed from the market reportedly for lack of effectiveness.

Bifemelane acts as a monoamine oxidase inhibitor (MAOI) of both isoenzymes, with competitive reversible inhibition of MAO-A (K_i = 4.20 μM), making it a reversible inhibitor of monoamine oxidase A (RIMA) and non-competitive irreversible inhibition of MAO-B (K_i = 46.0 μM), and also acts (weakly) as a norepinephrine reuptake inhibitor (NRI). The drug has nootropic, neuroprotective, and antidepressant-like effects in animal models, and appears to enhance the cholinergic system in the brain.