Chemistry:Noxiptiline

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Short description: Chemical 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)
  • In general: ℞ (Prescription only)
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
Chemical and physical data
FormulaC19H22N2O
Molar mass294.398 g·mol−1
3D model (JSmol)
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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.[1][2][3] It has imipramine-like effects,[4] acting as a serotonin and norepinephrine reuptake inhibitor, among other properties.[5][6] Of the TCAs, noxiptiline has been described as one of the most effective, rivaling amitriptyline in clinical efficacy.[7][8]

Synthesis

Ths synthesis is similar to that for Demexiptiline.

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Synthesis:[9][10] Patent:[11]

The condensation of dibenzosuberone (1) with hydroxylamine (2) gives the corresponding oxime [1785-74-6] (3). This is then reacted with 2-(dimethylamine)ethyl chloride [4584-46-7] (4).

References

  1. ↑ 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. https://books.google.com/books?id=5GpcTQD_L2oC&q=noxiptiline&pg=PA753. 
  2. ↑ Meyler's Side Effects of Psychiatric Drugs (Meylers Side Effects). Amsterdam: Elsevier Science. 2008. p. 34. ISBN 978-0-444-53266-4. https://books.google.com/books?id=s0XYvuPVgaAC&q=noxiptiline&pg=PA34. 
  3. ↑ Dictionary of organic compounds. London: Chapman & Hall. 1996. p. 4868. ISBN 0-412-54090-8. https://books.google.com/books?id=5S_uhYzKWisC&q=noxiptiline&pg=PA4868. 
  4. ↑ "Antidepressants". Drug actions: basic principles and therapeutic aspects. Stuttgart, Germany: Medpharm Scientific Pub. 1995. p. 127. ISBN 0-8493-7774-9. https://books.google.com/books?id=IvN4mZxraMkC&q=noxiptiline&pg=PA127. Retrieved January 30, 2013. 
  5. ↑ "Serotonin, dopamine and norepinephrine transporters in the central nervous system and their inhibitors". Progress in Drug Research. 54. Boston: Birkhauser. 2000. 59–119. doi:10.1007/978-3-0348-8391-7_3. ISBN 3-7643-6113-1. https://books.google.com/books?id=gwhdUGoO6KwC&q=noxiptiline%20fluvoxamine&pg=PA81. 
  6. ↑ "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. 1975. doi:10.1007/BF00500528. PMID 1161046. 
  7. ↑ "[Results of using tricyclic antidepressive drugs in the treatment of endogenous depression (comparative analysis of 7 drugs)]" (in pl). Psychiatria Polska 25 (3–4): 13–18. 1991. PMID 1687987. 
  8. ↑ "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. January 1975. doi:10.1055/s-0028-1094440. PMID 788000. 
  9. ↑ "[Basic tricyclic oxyiminoethers and their pharmacological properties]" (in German). Arzneimittel-Forschung 19: Suppl 5a:838+. June 1969. PMID 5819763. 
  10. ↑ "Synthesis of oxime esters and ethers as potential psychotropic agents". Journal of Pharmaceutical Sciences 54 (9): 1373–1376. September 1965. doi:10.1002/jps.2600540932. PMID 5881239. 
  11. ↑ Engelhard H, Engelhard N, Werth B, DE patent 1198353, issued 1965, assigned to HERMANN ENGELHARD DR ING



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