title: Oxaprotiline
text: # 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.
  
  ## Pharmacology
  
  Dextroprotiline acts as a potent norepinephrine reuptake inhibitor and $H_1$ receptor antagonist, as well as a very weak $α_1-adrenergic$ receptor antagonist. It has negligible affinity for the serotonin transporter, dopamine transporter, $α_2-adrenergic$ receptor, and muscarinic acetylcholine receptors. Whether it has any antagonistic effects on the $5-HT_2,$ $5-HT_7,$ or $D_2$ receptors like its relative maprotiline is unclear.
  
  Levoprotiline acts as a selective $H_1$ 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.
  
  