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Oxaprotiline

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Oxaprotiline
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
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC20H23NO
Molar mass293.410 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 checkY
  • Key:FDXQKWSTUZCCTM-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Oxaprotiline (developmental code nameC 49-802 BDA), also known ashydroxymaprotiline, is anorepinephrine reuptake inhibitor belonging to thetetracyclic antidepressant (TeCA) family and is related tomaprotiline. Though investigated as anantidepressant,[1] it was never marketed.

Pharmacology

[edit]

Dextroprotiline acts as apotentnorepinephrine reuptake inhibitor[2][3] andH1 receptorantagonist,[4] as well as a very weakα1-adrenergic receptorantagonist.[2][5] It has negligibleaffinity for theserotonin transporter,[2]dopamine transporter,α2-adrenergic receptor,[2][5] andmuscarinic acetylcholine receptors.[5] Whether it has anyantagonistic effects on the5-HT2,5-HT7, orD2 receptors like its relativemaprotiline is unclear.

Levoprotiline acts as aselectiveH1 receptorantagonist, with no affinity foradrenaline,dopamine,muscarinic acetylcholine, orserotoninreceptors, or any of themonoamine transporters.[2][3][4]

Chemistry

[edit]

Oxaprotiline is aracemic compound composed of twoisomers,R(−)- orlevo- oxaprotiline (levoprotiline;CGP-12,103-A), andS(+)- or dextro- oxaprotiline (dextroprotiline;CGP-12,104-A). Both enantiomers are active, with the levo- form acting as anantihistamine and the dextro- form having an additional pharmacology (seeabove), but with both unexpectedly still retaining antidepressant effects.[6]

See also

[edit]

References

[edit]
  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. ^abcdeWaldmeier 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. ^abReimann 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. ^abNoguchi 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. ^abcRichelson 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.
SSRIsTooltip Selective serotonin reuptake inhibitors
SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors
NRIsTooltip Norepinephrine reuptake inhibitors
NDRIsTooltip Norepinephrine–dopamine reuptake inhibitors
NaSSAsTooltip Noradrenergic and specific serotonergic antidepressants
SARIsTooltip Serotonin antagonist and reuptake inhibitors
SMSTooltip Serotonin modulator and stimulators
Others
TCAsTooltip Tricyclic antidepressants
TeCAsTooltip Tetracyclic antidepressants
Others
Non-selective
MAOATooltip Monoamine oxidase A-selective
MAOBTooltip Monoamine oxidase B-selective
Miscellaneous
α1
Agonists
Antagonists
α2
Agonists
Antagonists
β
Agonists
Antagonists
H1
Agonists
Antagonists
H2
Agonists
Antagonists
H3
Agonists
Antagonists
H4
Agonists
Antagonists
DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)
NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)
SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)
VMATsTooltip Vesicular monoamine transporters
Others
Classes
Antidepressants
(Tricyclic antidepressants(TCAs))
Antihistamines
Antipsychotics
Anticonvulsants
Anticholinergics
Others
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