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Noxiptiline

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Noxiptiline
Skeletal formula of noxiptilin
Space-filling model of the noxiptiline molecule
Clinical data
Trade namesAgedal, Elronon, Nogedal
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • BR: Class C1 (Other controlled substances)[1]
  • In general: ℞ (Prescription only)
Identifiers
  • 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-oneO-[2-dimethylamino)ethyl]oxime
CAS Number
PubChemCID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC19H22N2O
Molar mass294.398 g·mol−1
3D model (JSmol)
  • O(\N=C2\c1c(cccc1)CCc3c2cccc3)CCN(C)C
  • InChI=1S/C19H22N2O/c1-21(2)13-14-22-20-19-17-9-5-3-7-15(17)11-12-16-8-4-6-10-18(16)19/h3-10H,11-14H2,1-2H3 checkY
  • Key:GPTURHKXTUDRPC-UHFFFAOYSA-N checkY

Noxiptiline (brand namesAgedal,Elronon,Nogedal), also known asnoxiptyline anddibenzoxine, is atricyclic antidepressant (TCA) that was introduced inEurope in the 1970s for the treatment ofdepression.[2][3][4] It hasimipramine-like effects,[5] acting as aserotonin andnorepinephrine reuptake inhibitor, among other properties.[6][7] Of the TCAs, noxiptiline has been described as one of the most effective, rivalingamitriptyline in clinical efficacy.[8][9]

Synthesis

[edit]

The ketone dibenzosuberenone (1) is treated withhydroxylamine (2) to give itsketoxime (3). Base-catalyzedalkylation withClCH2CH2N(CH3)2 (4) yields noxiptiline.[10][11][12]

References

[edit]
  1. ^Anvisa (2023-03-31)."RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União (published 2023-04-04).Archived from the original on 2023-08-03. Retrieved2023-08-16.
  2. ^Swiss Pharmaceutical Society (2000).Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. p. 753.ISBN 3-88763-075-0.
  3. ^Aronson JK (2008).Meyler's Side Effects of Psychiatric Drugs (Meylers Side Effects). Amsterdam: Elsevier Science. p. 34.ISBN 978-0-444-53266-4.
  4. ^Dictionary of organic compounds. London: Chapman & Hall. 1996. p. 4868.ISBN 0-412-54090-8.
  5. ^Mutschler E (1995)."Antidepressants".Drug actions: basic principles and therapeutic aspects. Stuttgart, Germany: Medpharm Scientific Pub. p. 127.ISBN 0-8493-7774-9. RetrievedJanuary 30, 2013.
  6. ^Olivier B, Soudijn W, van Wijngaarden I (2000)."Serotonin, dopamine and norepinephrine transporters in the central nervous system and their inhibitors". In Jucker E, Ren S, Soudijn W, van Wijngaarden I, Kumari M, Poyner D, Bushfield M, Horikoshi H, Fujiwara T (eds.).Progress in Drug Research. Vol. 54. Boston: Birkhauser. pp. 59–119.doi:10.1007/978-3-0348-8391-7_3.ISBN 3-7643-6113-1.PMID 10857386.{{cite book}}:|journal= ignored (help)
  7. ^Barth N, Manns M, Muscholl E (1975). "Arrhythmias and inhibition of noradrenaline uptake caused by tricyclic antidepressants and chlorpromazine on the isolated perfused rabbit heart".Naunyn-Schmiedeberg's Archives of Pharmacology.288 (2–3):215–231.doi:10.1007/BF00500528.PMID 1161046.S2CID 11641400.
  8. ^Beresewicz M, Bidzińska E, Koszewska I, Puzyński S (1991). "[Results of using tricyclic antidepressive drugs in the treatment of endogenous depression (comparative analysis of 7 drugs)]".Psychiatria Polska (in Polish).25 (3–4):13–18.PMID 1687987.
  9. ^Lingjaerde O, Asker T, Bugge A, Engstrand E, Eide A, Grinaker H, et al. (January 1975). "Noxiptilin (Agedal)--a new tricyclic antidepressant with a faster onset of action? A double-blind, multicentre comparison with amitriptyline".Pharmakopsychiatrie, Neuro-Psychopharmakologie.8 (1):26–35.doi:10.1055/s-0028-1094440.PMID 788000.S2CID 44886111.
  10. ^Aichinger G, Behner O, Hoffmeister F, Schütz S (June 1969). "Basic tricyclic oxyiminoethers and their pharmacological properties".Arzneimittel-Forschung (in German).19: Suppl 5a:838+.PMID 5819763.
  11. ^US 3963778, Schütz S, Behner O, Hoffmeister F, "Basic oximes and their preparation", issued 1976-06-15, assigned to Bayer AG 
  12. ^Wylie BB, Isaacson EI, Delgado JN (September 1965). "Synthesis of oxime esters and ethers as potential psychotropic agents".Journal of Pharmaceutical Sciences.54 (9):1373–1376.doi:10.1002/jps.2600540932.PMID 5881239.
SSRIsTooltip Selective serotonin reuptake inhibitors
SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors
NRIsTooltip Norepinephrine reuptake inhibitors
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