Oxaprotiline

Oxaprotiline

Clinical data
Routes of administration	Oral
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name (±)-3-(9,10-ethano-9,10-dihydro-9-anthryl)-1-methylamino-2-propanol
CAS Number	56433-44-4 N
PubChem CID	38207
ChemSpider	35026 Y
UNII	3V3Z2HK4LS
ChEMBL	ChEMBL1213009 Y
Chemical and physical data
Formula	C20H23NO
Molar mass	293.410 g·mol−1
3D 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 Y Key:FDXQKWSTUZCCTM-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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 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.

See also

• Maprotiline