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]