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Oxaprotiline
Systematic (IUPAC) name
(±)-3-(9,10-ethano-9,10-dihydro-9-anthryl)-1-methylamino-2-propanol
Identifiers
CAS number 56433-44-4
ATC code  ?
PubChem 38207
ChemSpider 35026
Chemical data
Formula C20H23NO
Mol. mass 293.40 g/mol
SMILES eMolecules & PubChem
Therapeutic considerations
Pregnancy cat.  ?
Legal status Uncontrolled
Routes Oral

Oxaprotiline, also known as hydroxymaprotiline, is a psychoactive drug and research chemical of the tetracylic chemical class. Though investigated as an antidepressant,[1] it was never developed and marketed for clinical use.

Contents

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 merely as an antihistamine and the dextro- form having a more expansive pharmacology (see below), but with both curiously still retaining antidepressant effects.[2]

Pharmacology

Dextroprotiline acts as a potent norepinephrine reuptake inhibitor[3][4] and H1 receptor antagonist,[5] as well as a very weak α1-adrenergic receptor antagonist.[6][3] It has negligible affinity for the serotonin transporter,[3] dopamine transporter, α2-adrenergic receptor,[6][3] and muscarinic acetylcholine receptors.[6] Whether it has any antagonistic effects on the 5-HT2 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.[5][3][4]

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. PMID 3527706. 
  2. ^ 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. 
  3. ^ a b c d e 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. PMID 7115436. 
  4. ^ a b 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. PMID 8382162. 
  5. ^ a b 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. PMID 1353628. 
  6. ^ a b c 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. http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=6086881. 
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