Carfenazine

Carfenazine

Carfenazine

Chemical compound

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former developmental code name NSC-71755), is an antipsychotic and tranquilizer of the phenothiazine group that was withdrawn from the market.[1][2][3]

Quick Facts Clinical data, Other names ...

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. [1]
    Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 224–. ISBN 978-1-4757-2085-3.
  2. [2]
    William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 862–. ISBN 978-0-8155-1856-3.
  3. [3]
    Briggs GG, Freeman RK, Yaffe SJ (2011). Drugs in Pregnancy and Lactation: A Reference Guide to Fetal and Neonatal Risk. Lippincott Williams & Wilkins. pp. 213–. ISBN 978-1-60831-708-0.
  4. [4]
    Zhuraulev, S.V. et al, Zh. Obshch. Khim., 1962, 32, 2244
  5. [5]
    M. H. Sherlock, N. Sperber, U.S. patent 2,985,654 (1961 to Schering)
  6. [6]
    R. F. Tislow et al., U.S. patent 3,023,146 (1962 to American Home Products).



Stub icon

This drug article relating to the nervous system is a stub. You can help Wikipedia by expanding it.
Share this article:

This article uses material from the Wikipedia article Carfenazine, and is written by contributors. Text is available under a CC BY-SA 4.0 International License; additional terms may apply. Images, videos and audio are available under their respective licenses.