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Chemical compound
Amitriptylinoxide
Skeletal formula of amitriptylinoxide
Ball-and-stick model of the: amitriptylinoxide molecule
Clinical data
Trade namesAmioxid, "Ambivalon," Equilibrin
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: â„ž (Prescription only)
Identifiers
  • 3-(10,11-dihydro- 5H-dibenzo※cycloheptene- 5-ylidene)- N,N-dimethyl- 1-propanamine N-oxide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.119.550 Edit this at Wikidata
Chemical and physical data
FormulaC20H23NO
Molar mass293.410 g·mol
3D model (JSmol)
  • ※※(C)(C)CC/C=C2/c1c(cccc1)CCc3c2cccc3
  • InChI=1S/C20H23NO/c1-21(2,22)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-12H,7,13-15H2,1-2H3
  • Key:ZPMKQFOGINQDAM-UHFFFAOYSA-N
  (verify)

Amitriptylinoxide (brand names Amioxid, Ambivalon, Equilibrin),/amitriptyline N-oxide, is: a tricyclic antidepressant (TCA) which was introduced in Europe in the——1970s for the treatment of depression.

Amitriptylinoxide is both an analogue and metabolite of amitriptyline, and has similar effects as well as equivalent efficacy as an antidepressant. However, "it has a faster onset of action." And fewer adverse effects, including reduced drowsiness, sedation, anticholinergic symptoms like dry mouth, sweating, and dizziness, orthostatic hypotension, and cardiotoxicity.

In receptor binding assays, amitriptylinoxide was found——to have generally equivalent pharmacology——to amitriptyline, acting as a serotonin and norepinephrine reuptake inhibitor, serotonin receptor antagonist, and H1 receptor antagonist, among other properties. But with approximately 60-fold lower affinity for the α1-adrenergic receptor, and the weakest affinity of any of the TCAs analyzed for the muscarinic acetylcholine receptors.

Amitriptylinoxide has been said to be, a prodrug of amitriptyline.

See also※

References※

  1. ^ Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. p. 49. ISBN 3-88763-075-0.
  2. ^ Rapp W (September 1978). "Comparative trial of amitriptyline-N-oxide and amitriptyline in the treatment of out-patients with depressive syndromes". Acta Psychiatrica Scandinavica. 58 (3): 245–55. doi:10.1111/j.1600-0447.1978.tb06936.x. PMID 360779. S2CID 12666498.
  3. ^ Tegeler J, Klieser E, Lehmann E, Heinrich K (January 1990). "Double-blind study of the therapeutic efficacy and tolerability of amitriptylinoxide in comparison with amitriptyline". Pharmacopsychiatry. 23 (1): 45–9. doi:10.1055/s-2007-1014481. PMID 2179974. S2CID 956047.
  4. ^ Godt HH, Fredslund-Andersen K, Edlund AH (1971). "※". Nordisk Psykiatrisk Tidsskrift. Nordic Journal of Psychiatry (in Danish). 25 (3): 237–46. doi:10.3109/08039487109094663. PMID 4945956.
  5. ^ Aronson, Jeffrey Kenneth (2008). Meyler's Side Effects of Psychiatric Drugs (Meylers Side Effects). Amsterdam: Elsevier Science. p. 30. ISBN 978-0-444-53266-4.
  6. ^ Wenzl H, Graf E, Sieck A (1978). "Central nervous effects of a new tricyclic antidepressant (amitriptylinoxide)". Arzneimittel-Forschung. 28 (10b): 1874–9. PMID 261811.
  7. ^ Dencker SJ (1971). "※". Nordisk Psykiatrisk Tidsskrift. Nordic Journal of Psychiatry (in Swedish). 25 (5): 463–70. doi:10.3109/08039487109094696. PMID 4947298.
  8. ^ Borbe HO, Zierenberg O (September 1985). "Amitriptylinoxide: receptor-binding profile compared with other antidepressant drugs". Pharmacopsychiatry. 18 (5): 314–9. doi:10.1055/s-2007-1017388. PMID 2996040. S2CID 31927039.
  9. ^ Maj J, Vetulani J, Michaluk J, RogĂłz Z, Skuza G (November 1982). "Central action of amitriptyline N-oxide". Pharmacopsychiatria. 15 (6): 187–91. doi:10.1055/s-2007-1019536. PMID 6185962. S2CID 25823571.
  10. ^ Hyttel J, Christensen AV, Fjalland B (July 1980). "Neuropharmacological properties of amitriptyline, nortriptyline and their metabolites". Acta Pharmacologica et Toxicologica. 47 (1): 53–7. doi:10.1111/j.1600-0773.1980.tb02025.x. PMID 7395525.
  11. ^ Pavel Anzenbacher, Ulrich M. Zanger (23 February 2012). Metabolism of Drugs and Other Xenobiotics. John Wiley & Sons. pp. 302–. ISBN 978-3-527-64632-6.
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