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 namesDeparon, Tinoran
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-life35 hours[1]
Identifiers
IUPAC name
  • 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
FormulaC18H18N2O
Molar mass278.355 g·mol−1
3D model (JSmol)
SMILES
  • O(\N=C3/c1ccccc1\C=C/c2c3cccc2)CCNC

Synthesis

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

Synthesis:[5] Patents:[6][7]

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).

References
  1. Florencio Zaragoza Dörwald (4 February 2013). Lead Optimization for Medicinal Chemists: Pharmacokinetic Properties of Functional Groups and Organic Compounds. John Wiley & Sons. pp. 313–. ISBN 978-3-527-64565-7.
  2. Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. p. 301. ISBN 3-88763-075-0.
  3. David J. Triggle (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. p. 583. ISBN 0-412-46630-9.
  4. Teste JF, Pelsy-Johann I, Decelle T, Boulu RG (1993). "Anti-immobility activity of different antidepressant drugs using the tail suspension test in normal or reserpinized mice". Fundamental & Clinical Pharmacology. 7 (5): 219–26. doi:10.1111/j.1472-8206.1993.tb00235.x. PMID 8370568. S2CID 24240307.
  5. Aichinger G, Behner O, Hoffmeister F, Schütz S. Basische tricyclische Oxyiminoäther und ihre pharmakologischen Eigenschaften [Basic tricyclic oxyiminoethers and their pharmacological properties]. Arzneimittelforschung. 1969 Jun;19:Suppl 5a:838+. German. PMID: 5819763.
  6. Siegismund Schutz, Otto Behner, & Friedrich Hoffmeister, U.S. Patent 3,989,844 & U.S. Patent 3,963,778 (both 1976 to Bayer AG).
  7. Dr Sigismund Schuetz, Dr Otto Behner, Dr Friedrich Hoffmeister, DE 1247302 (1967 to Bayer Ag).

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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