Propizepine

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Propizepine
Propizepine.png
Systematic (IUPAC) name
6-(2-dimethylaminopropyl)-11H-pyrido[3,2-c][1,5]benzodiazepin-5-one
Clinical data
Legal status
  • Prescription only
Routes Oral
Identifiers
CAS number 10321-12-7
14559-79-6 (hydrochloride)
ATC code None
PubChem CID 112029
ChemSpider 100443
UNII 09B57945V9 YesY
ChEMBL CHEMBL2104749
Chemical data
Formula C17H20N4O 
Mol. mass 296.37 g/mol

Propizepine (Depressin, Vagran) is a tricyclic antidepressant (TCA) used in France for the treatment of depression which was introduced in the 1970s.[1][2][3][4]

Synthesis[edit]

one of the benzene rings in dibenzepin () can be replaced by pyridine. In a one-pot reaction, condensation of the 2-chloronicotinic acid () with ortho-phenylenediamine () leads to the lactam (). The order in which the two steps, aromatic displacement and amide formation, take place has not been elucidated. Simple alkylation of the anion from the product with 3-chloro-2-(N,N-dimethylamino)propane () affords the antidepressant agent propizepine ().[5]

Propizepine synthesis.png

See also[edit]

References[edit]

  1. ^ Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. p. 888. ISBN 3-88763-075-0. 
  2. ^ David J. Triggle (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. p. 1680. ISBN 0-412-46630-9. 
  3. ^ Niels F. Muller, Rudolf P. Dessing, European Society of Clinical Pharmacy (1997). European Drug Index, Volume 33. CRC Press. p. 1339. ISBN 3-7692-2114-1. 
  4. ^ Dereux JF (1976). "[Vagran 50: a situational antidepressant]". Semaine des Hôpitaux. Thérapeutique (in French) 52 (7-8): 385–8. PMID 996559. 
  5. ^ Hoffmann, C.; Faure, A.; Bull. Soc. Chim. Fr. 1966, 2316.