Noxiptiline

Chemical compound From Wikipedia, the free encyclopedia

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]

Trade namesAgedal, Elronon, Nogedal
ATC code
  • none
Legal status
  • BR: Class C1 (Other controlled substances)[1]
  • In general: ℞ (Prescription only)
Quick facts Clinical data, Trade names ...
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
CAS Number
PubChem CID
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
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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

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