binedaline binedaline binedaline (also called binodaline or binedaline hydrochloride;) is a drug that was investigated as an antidepressant in the 1980s but was never marketed. it acts as a selective norepinephrine reuptake inhibitor (ki = 25 nm), with relatively insignificant influence on the serotonin (ki = 847 nm) and dopamine (ki >= 2 μm) transporters. it has negligible affinity for the α-adrenergic, mach, h1, or 5-ht2 receptors. binedalineclinical dataroutes ofadministrationoralatc codenonelegal statuslegal status in general: unscheduled identifiers iupac name n,n,n-trimethyl-n-(3-phenylindol-1-yl)ethane-1,2-diamine cas number60662-16-0 npubchem cid42510chemspider38769 yunii3avg9p140rchemblchembl2104611 ncomptox dashboard (epa)dtxsid20209472 chemical and physical dataformulac19h23n3molar mass293.414 g·mol−13d model (jsmol)interactive image smiles c1cccc2c1c(cn2n(ccn(c)c)c)c3ccccc3 inchi inchi=1s/c19h23n3/c1-20(2)13-14-21(3)22-15-18(16-9-5-4-6-10-16)17-11-7-8-12-19(17)22/h4-12,15h,13-14h2,1-3h3 ykey:sxyffmxpddgoek-uhfffaoysa-n y ny (what is this?) (verify) synthesis thieme synthesis: patents: grignard reaction of 2-aminobenzophenone (1) with methylmagnesium bromide and dehydration of the tertiary carbinol gives 2-(1-phenylvinyl)aniline (2). in an example of the widman‐stoermer synthesis, treatment with nitrous acid followed by basification of the diazonium species with ammonia causes an intramolecular cyclization to afford 4-phenylcinnoline (3). hydrogenation would give 4-phenyl-1,4-dihydrocinnoline, cid:14175750 (4). the presence of acetic acid gives (5). the reaction with methyl p-toluenesulfonate leads to cid:20337750 (6). acid hydrolysis gives n-methyl-3-phenylindol-1-amine (7). sodamide is then used to abstract the amine proton; alkylation of then anionic species with 2-dimethylaminoethylchloride (8) then concludes the synthesis of binedaline (9).