Chemistry:Carfenazine

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Short description: Chemical compound
Carfenazine
Carphenazine.svg
Clinical data
Other namesProketazine, Carphenazin
License data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • Withdrawn
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
Chemical and physical data
FormulaC24H31N3O2S
Molar mass425.59 g·mol−1
3D model (JSmol)

Carfenazine (INN) (former developmental code name WY-2445), or carphenazine (BAN), also known as carphenazine maleate (USAN) (brand name Proketazine; former developmental code name NSC-71755), is an antipsychotic and tranquilizer of the phenothiazine group that was withdrawn from the market.[1][2][3]

Synthesis

Thieme Synthesis:[4] Patent:[5][6]

The alkylation reaction between 2-Propionyl Phenothiazine [92-33-1] (1) and 1-Bromo-3-chloropropane (2) gives 1-[10-(3-chloropropyl)phenothiazin-2-yl]propan-1-one [95157-45-2] (3). A second alkylation step, this time with 2-(1-Piperazinyl)ethanol [103-76-4] (4) completes the synthesis of Carfenazine (5).

NB: Although above procedure is proof-of-concept, bear in mind no protecting group {Other patent uses ketalization technique}

Analogues

References

  1. ↑ The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 224–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA224. 
  2. ↑ William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 862–. ISBN 978-0-8155-1856-3. https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA862. 
  3. ↑ Drugs in Pregnancy and Lactation: A Reference Guide to Fetal and Neonatal Risk. Lippincott Williams & Wilkins. 2011. pp. 213–. ISBN 978-1-60831-708-0. https://books.google.com/books?id=OIgTE4aynrMC&pg=PA213. 
  4. ↑ Zhuraulev, S.V. et al, Zh. Obshch. Khim., 1962, 32, 2244
  5. ↑ M. H. Sherlock, N. Sperber, U.S. Patent 2,985,654 (1961 to Schering)
  6. ↑ R. F. Tislow et al., U.S. Patent 3,023,146 (1962 to American Home Products).





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