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Tricyclic antidepressant
Demexiptiline
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Demexiptiline

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Demexiptiline
Skeletal formula of demexiptiline
Space-filling model of the demexiptiline molecule
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
Identifiers
  • 5H-dibenzo(a,d)cyclohepten-5-one O-(2-(methylamino)ethyl)oxime
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C18H18N2O
Molar mass 278.355 g·mol−1
3D model (JSmol)
  • O(\N=C3/c1ccccc1\C=C/c2c3cccc2)CCNC

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

Synthesis

The synthesis is similar to that reported for Noxiptiline but also differs in a couple of respects.

Synthesis: Patents:

The condensation between Dibenzosuberenone [2222-33-5] (1) and hydroxylamine (2) gives the oxime, [1021-91-6] (3). Base catalyzed attachment of the sidechain by reaction with 2-Chloro-N-Methylethanamine [32315-92-7] (4) completed the synthesis of demexiptiline (5).

Further reading

  • Martin A, Masson JM, Jusseaume P, Beloncle M, Voisinet C (November 1981). "[Demexiptiline in the treatment of melancholic states (reflections after 3 years of use)]". Annales médico-psychologiques (in French). 139 (9): 1023–35. PMID 7337336.



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