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Cericlamine

Cericlamine
Cericlamine.svg
Clinical data
Routes of
administration
Oral[1]
ATC code
  • None
Pharmacokinetic data
Elimination half-life8 hours[1]
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC12H17Cl2NO
Molar mass262.17 g·mol−1
3D model (JSmol)

Cericlamine (INN; developmental code JO-1017) is a potent and moderately selective serotonin reuptake inhibitor (SSRI) of the amphetamine family (specifically, a derivative of phentermine, and closely related to chlorphentermine, a highly selective serotonin releasing agent) that was investigated as an antidepressant for the treatment of depression, anxiety disorders, and anorexia nervosa by Jouveinal but did not complete development and was never marketed.[1][2][3][4] It reached phase III clinical trials in 1996 before development was discontinued in 1999.[5]

Synthesis

Cericlamine synthesis:[6]

Arylation of methacrylic acid with a diazonium salt of 3,4-dichloroaniline (or 3,4-dichloro-benzenediazonium salt), is carried out according to the Meerwein reaction catalysed by a metallic halide. For the next step, the halide is displaced by dimethylamine, then esterification is performed, followed by reduction with a metal hydride.

See also

References

  1. ^ a b c Darcourt, G.; Tessera, M.; Lesaunier, R.; Engrand, P.; Scherrer, B.; Dreyfus, J. F.; Bogaievsky, Y. (1992). "A MULTICENTRE DOUBLE-BLIND, PLACEBO-CONTROLLED DOSE-FINDING STUDY WITH CERICLAMINE IN MAJOR DEPRESSION". Clinical Neuropharmacology. 15: 176B. doi:10.1097/00002826-199202001-00339. ISSN 0362-5664.
  2. ^ Crow, Scott; Brown, Eric (2003). "Investigational drugs for eating disorders". Expert Opinion on Investigational Drugs. 12 (3): 491–499. doi:10.1517/13543784.12.3.491. ISSN 1354-3784.
  3. ^ Ramesh N. Patel (3 January 2000). Stereoselective Biocatalysis. CRC Press. pp. 48–. ISBN 978-0-8247-8282-5.
  4. ^ Lily C. Tang; Stephen J. Tang (6 December 2012). Neurochemistry in Clinical Application. Springer Science & Business Media. pp. 81–. ISBN 978-1-4615-1857-0.
  5. ^ AdisInsight. "Cericlamine". Retrieved 13 January 2016.
  6. ^ U.S. Patent 6,121,491