Oxaprotiline

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Oxaprotiline
Oxaprotiline.svg
Clinical data
Routes of
administration 		Oral
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • (±)-3-(9,10-ethano-9,10-dihydro-9-anthryl)-1-methylamino-2-propanol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C20H23NO
Molar mass 293.410 g·mol−1
3D model (JSmol)
  • CNCC(CC12CCC(C3=CC=CC=C31)C4=CC=CC=C24)O
  • 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 Yes check.svgY
  • Key:FDXQKWSTUZCCTM-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (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, [1] it was never marketed.

Contents

Pharmacology

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]

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. [6]

See also

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. 1 2 3 4 5 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. 1 2 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. 1 2 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. 1 2 3 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.
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