Noxiptiline

Source: Wikipedia, the free encyclopedia.
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-one O-[2-dimethylamino)ethyl]oxime
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
 ☒NcheckY (what is this?)  (verify)

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]

Synthesis

Ths synthesis is similar to that for Demexiptiline.

Synthesis:[10][11] Patent:[12]

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. ^ 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.
  2. ISBN 3-88763-075-0
    .
  3. ISBN 978-0-444-53266-4
    .
  4. ISBN 0-412-54090-8
    .
  5. ISBN 0-8493-7774-9
    . Retrieved January 30, 2013.
  6. PMID 10857386. {{cite book}}: |journal= ignored (help
    )
  7. S2CID 11641400
    .
  8. PMID 1687987
    .
  9. S2CID 44886111
    .
  10. PMID 5819763
    .
  11. PMID 5881239
    .
  12. ^ DE 1198353, Engelhard H, Engelhard N, Werth B, issued 1965, assigned to HERMANN ENGELHARD DR ING