Noxiptiline

Noxiptiline (brand names Agedal, Elronon, Nogedal), also known as noxiptyline and dibenzoxine, is a tricyclic antidepressant (TCA) that was introduced in Europe in the 1970s for the treatment of depression.^[2]^[3]^[4] It has imipramine-like effects,^[5] acting as a serotonin and norepinephrine reuptake inhibitor, among other properties.^[6]^[7] Of the TCAs, noxiptiline has been described as one of the most effective, rivaling amitriptyline in clinical efficacy.^[8]^[9]

Noxiptiline
Clinical data


Trade names	Agedal, 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
IUPAC name 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one O-[2-dimethylamino)ethyl]oxime
CAS Number	3362-45-6^Y HCl: 4985-15-3^Y
PubChem CID	21087
ChemSpider	19832^Y
UNII	DF7D3NY7EL HCl: PNW59W2B94^Y
ChEBI	CHEBI:135232
ChEMBL	ChEMBL1697689^Y
CompTox Dashboard (EPA)	DTXSID10187311
Chemical and physical data
Formula	C₁₉H₂₂N₂O
Molar mass	294.398 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O(\N=C2\c1c(cccc1)CCc3c2cccc3)CCN(C)C
InChI 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^Y Key:GPTURHKXTUDRPC-UHFFFAOYSA-N^Y

Synthesis

The ketone dibenzosuberenone (1) is treated with hydroxylamine (2) to give its ketoxime (3). Base-catalyzed alkylation with ClCH₂CH₂N(CH₃)₂ (4) yields noxiptiline.^[10]^[11]^[12]

References

^ 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. Retrieved 2023-08-16.

^ 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.

^ Aronson JK (2008). Meyler's Side Effects of Psychiatric Drugs (Meylers Side Effects). Amsterdam: Elsevier Science. p. 34. ISBN 978-0-444-53266-4.

^ Dictionary of organic compounds. London: Chapman & Hall. 1996. p. 4868. ISBN 0-412-54090-8.

^ Mutschler E (1995). "Antidepressants". Drug actions: basic principles and therapeutic aspects. Stuttgart, Germany: Medpharm Scientific Pub. p. 127. ISBN 0-8493-7774-9. Retrieved January 30, 2013.

^ 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.

^ 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.

^ 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.

^ 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.

^ 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.

^ US 3963778, Schütz S, Behner O, Hoffmeister F, "Basic oximes and their preparation", issued 1976-06-15, assigned to Bayer AG

^ 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.

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