oxaprotiline oxaprotiline oxaprotiline (developmental code name c 49-802 bda), also known as hydroxymaprotiline, is a norepinephrine reuptake inhibitor belonging to the tetracyclic antidepressant (teca) family and is related to maprotiline. though investigated as an antidepressant, it was never marketed. oxaprotilineclinical dataroutes ofadministrationorallegal statuslegal status in general: uncontrolled identifiers iupac name (±)-3-(9,10-ethano-9,10-dihydro-9-anthryl)-1-methylamino-2-propanol cas number56433-44-4 npubchem cid38207chemspider35026 yunii3v3z2hk4lschemblchembl1213009 ychemical and physical dataformulac20h23nomolar mass293.410 g·mol−13d model (jsmol)interactive image smiles cncc(cc12ccc(c3=cc=cc=c31)c4=cc=cc=c24)o inchi inchi=1s/c20h23no/c1-21-13-14(22)12-20-11-10-15(16-6-2-4-8-18(16)20)17-7-3-5-9-19(17)20/h2-9,14-15,21-22h,10-13h2,1h3 ykey:fdxqkwstuzcctm-uhfffaoysa-n y ny (what is this?) (verify) pharmacology dextroprotiline acts as a potent norepinephrine reuptake inhibitor and h1 receptor antagonist, as well as a very weak α1-adrenergic receptor antagonist. it has negligible affinity for the serotonin transporter, dopamine transporter, α2-adrenergic receptor, and muscarinic acetylcholine receptors. whether it has any antagonistic effects on the 5-ht2, 5-ht7, or d2 receptors like its relative maprotiline is unclear. levoprotiline acts as a selective h1 receptor antagonist, with no affinity for adrenaline, dopamine, muscarinic acetylcholine, or serotonin receptors, or any of the monoamine transporters. chemistry oxaprotiline is a racemic compound composed of two isomers, r(−)- or levo- oxaprotiline (levoprotiline; cgp-12,103-a), and s(+)- or dextro- oxaprotiline (dextroprotiline; cgp-12,104-a). both enantiomers are active, with the levo- form acting as an antihistamine and the dextro- form having an additional pharmacology (see above), but with both unexpectedly still retaining antidepressant effects.