Oxaprotiline
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| Systematic (IUPAC) name | |
| (±)-3-(9,10-ethano-9,10-dihydro-9-anthryl)-1-methylamino-2-propanol | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | Uncontrolled |
| Routes | Oral |
| Identifiers | |
| CAS number | 56433-44-4  |
| ATC code | ? |
| PubChem | CID 38207 |
| ChemSpider | 35026  |
| UNII | 3V3Z2HK4LS |
| ChEMBL | CHEMBL1213009 |
| Chemical data | |
| Formula | C20H23NO |
| Mol. mass | 293.40 g/mol |
| SMILES | eMolecules & PubChem |
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Oxaprotiline, also known as hydroxymaprotiline, is a psychoactive drug and research chemical of the tetracyclic chemical class. Though investigated as an antidepressant,[1] it was never developed and marketed for clinical use.
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[edit] 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]
[edit] 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.[3][6] It has negligible affinity for the serotonin transporter,[3] dopamine transporter, α2-adrenergic receptor,[3][6] 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.[3][4][5]
[edit] See also
[edit] References
- ^ 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.
- ^ 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.
- ^ 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. doi:10.1016/0006-2952(82)90510-X. PMID 7115436.
- ^ 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. doi:10.1007/BF00315288. PMID 8382162.
- ^ 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. doi:10.1016/0031-9384(92)90297-F. PMID 1353628.
- ^ 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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