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,[1] it was never marketed.
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Routes of administration | Oral |
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Formula | C20H23NO |
Molar mass | 293.410 g·mol−1 |
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Dextroprotiline acts as a potent norepinephrine reuptake inhibitor[2][3] and H1 receptor antagonist,[4] as well as a very weak α1-adrenergic receptor antagonist.[2][5] It has negligible affinity for the serotonin transporter,[2] dopamine transporter, α2-adrenergic receptor,[2][5] and muscarinic acetylcholine receptors.[5] 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.[2][3][4]
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.[6]