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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
PubChem CID	38207
ChemSpider	35026
UNII	3V3Z2HK4LS
ChEMBL	ChEMBL1213009
CompTox Dashboard (EPA)	DTXSID40866561
Chemical and physical data
Formula	C20H23NO
Molar mass	293.410 g·mol
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 Key:FDXQKWSTUZCCTM-UHFFFAOYSA-N
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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

References

1. Giedke H, Gaertner H, Breyer-Pfaff U, Rein W, Axmann D (1986). "Amitriptyline and oxaprotiline in the treatment of hospitalized depressive patients. Clinical aspects, psychophysiology, and drug plasma levels". European Archives of Psychiatry and Neurological Sciences. 235 (6): 329–338. doi:10.1007/bf00381001. PMID 3527706. S2CID 24152419.
2. ^ Waldmeier PC, Baumann PA, Hauser K, Maitre L, Storni A (June 1982). "Oxaprotiline, a noradrenaline uptake inhibitor with an active and an inactive enantiomer". Biochemical Pharmacology. 31 (12): 2169–76. doi:10.1016/0006-2952(82)90510-X. PMID 7115436.
3. ^ Reimann IW, Firkusny L, Antonin KH, Bieck PR (1993). "Oxaprotiline: enantioselective noradrenaline uptake inhibition indicated by intravenous amine pressor tests but not alpha 2-adrenoceptor binding to intact platelets in man". European Journal of Clinical Pharmacology. 44 (1): 93–5. doi:10.1007/BF00315288. PMID 8382162. S2CID 22691825.
4. ^ Noguchi S, Inukai T, Kuno T, Tanaka C (June 1992). "The suppression of olfactory bulbectomy-induced muricide by antidepressants and antihistamines via histamine H1 receptor blocking". Physiology & Behavior. 51 (6): 1123–7. doi:10.1016/0031-9384(92)90297-F. PMID 1353628. S2CID 29562845.
5. ^ Richelson E, Nelson A (July 1984). "Antagonism by antidepressants of neurotransmitter receptors of normal human brain in vitro". The Journal of Pharmacology and Experimental Therapeutics. 230 (1): 94–102. PMID 6086881.
6. Noguchi S, Fukuda Y, Inukai T (May 1992). "Possible contributory role of the central histaminergic system in the forced swimming model". Arzneimittel-Forschung. 42 (5): 611–3. PMID 1530672.

• Secondary alcohols
• Amines
• Anthracenes
• Tetracyclic antidepressants