Demexiptiline

Demexiptiline (brand names Deparon, Tinoran) is a tricyclic antidepressant (TCA) used in France for the treatment of depression.^[2][3] It acts primarily as a norepinephrine reuptake inhibitor similarly to desipramine.^[4]

Demexiptiline

Clinical data
Trade names	Deparon, Tinoran
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-life	35 hours[1]
Identifiers
IUPAC name 5H-dibenzo(a,d)cyclohepten-5-one O-(2-(methylamino)ethyl)oxime
CAS Number	24701-51-7 Y
PubChem CID	28876
DrugBank	DB08998 Y
ChemSpider	26858
UNII	EYX738UZ5P
ChEMBL	ChEMBL2107576
CompTox Dashboard (EPA)	DTXSID40179441
Chemical and physical data
Formula	C18H18N2O
Molar mass	278.355 g·mol−1
3D model (JSmol)	Interactive image
SMILES O(\N=C3/c1ccccc1\C=C/c2c3cccc2)CCNC

Synthesis

The ketone dibenzosuberenone (1) is treated with hydroxylamine (2) to give its ketoxime (3). Base-catalyzed alkylation with ClCH₂CH₂NHCH₃ (4) yields demexiptiline.^[5][6]