|Chemical and physical data|
|Molar mass||293.40 g/mol|
|3D model (Jmol)|
|(what is this?)|
Oxaprotiline (C 49-802 BDA), also known as hydroxymaprotiline, is a norepinephrine reuptake inhibitor of the tetracyclic antidepressant family that is related to maprotiline. Though investigated as an antidepressant, it was never marketed.
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 merely as an antihistamine and the dextro- form having a more expansive pharmacology (see below), but with both unexpectedly still retaining antidepressant effects.
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 or D2 receptors like its relative maprotiline is unclear.
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