Chemistry:Demexiptiline

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Short description: Chemical compound
Demexiptiline
Skeletal formula of demexiptiline
Space-filling model of the demexiptiline molecule
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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC18H18N2O
Molar mass278.355 g·mol−1
3D model (JSmol)

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]

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. ↑ Lead Optimization for Medicinal Chemists: Pharmacokinetic Properties of Functional Groups and Organic Compounds. John Wiley & Sons. 4 February 2013. pp. 313–. ISBN 978-3-527-64565-7. https://books.google.com/books?id=YTeY9ZEfNccC&pg=PA313. 
  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. https://books.google.com/books?id=5GpcTQD_L2oC&q=demexiptiline&pg=PA301. 
  3. ↑ Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. 1996. p. 583. ISBN 0-412-46630-9. https://books.google.com/books?id=DeX7jgInYFMC&q=demexiptiline&pg=RA1-PA583. 
  4. ↑ "Anti-immobility activity of different antidepressant drugs using the tail suspension test in normal or reserpinized mice". Fundamental & Clinical Pharmacology 7 (5): 219–26. 1993. doi:10.1111/j.1472-8206.1993.tb00235.x. PMID 8370568. 
  5. ↑ "[Basic tricyclic oxyiminoethers and their pharmacological properties]". Arzneimittel-Forschung 19: Suppl 5a:838+. June 1969. PMID 5819763. 
  6. ↑ Schütz S, Behner O, Hoffmeister F, US patent 3989844, issued 1976, assigned to Bayer AG. & U.S. Patent 3,963,778
  7. ↑ Schütz S, Behner O, Hoffmeister F, DE patent 1247302, issued 1967, assigned to Bayer AG.

Further reading

  • "[Demexiptiline in the treatment of melancholic states (reflections after 3 years of use)]" (in fr). Annales médico-psychologiques 139 (9): 1023–35. November 1981. PMID 7337336. 




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