Chemistry:Oxaprotiline

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Short description: Chemical compound
Oxaprotiline
Oxaprotiline.svg
Clinical data
Routes of
administration
Oral
Legal status
Legal status
  • In general: uncontrolled
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC20H23NO
Molar mass293.410 g·mol−1
3D model (JSmol)
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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,[1] it was never marketed.

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. "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. 1986. doi:10.1007/bf00381001. PMID 3527706. https://pubmed.ncbi.nlm.nih.gov/3527706/. 
  2. 2.0 2.1 2.2 2.3 2.4 "Oxaprotiline, a noradrenaline uptake inhibitor with an active and an inactive enantiomer". Biochemical Pharmacology 31 (12): 2169–76. June 1982. doi:10.1016/0006-2952(82)90510-X. PMID 7115436. 
  3. 3.0 3.1 "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. 1993. doi:10.1007/BF00315288. PMID 8382162. 
  4. 4.0 4.1 "The suppression of olfactory bulbectomy-induced muricide by antidepressants and antihistamines via histamine H1 receptor blocking". Physiology & Behavior 51 (6): 1123–7. June 1992. doi:10.1016/0031-9384(92)90297-F. PMID 1353628. 
  5. 5.0 5.1 5.2 "Antagonism by antidepressants of neurotransmitter receptors of normal human brain in vitro". The Journal of Pharmacology and Experimental Therapeutics 230 (1): 94–102. July 1984. PMID 6086881. http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=6086881. 
  6. "Possible contributory role of the central histaminergic system in the forced swimming model". Arzneimittel-Forschung 42 (5): 611–3. May 1992. PMID 1530672.