Carfenazine Explained

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former developmental code name NSC-71755), is an antipsychotic and tranquilizer of the phenothiazine group that was withdrawn from the market.^{[1] [2] [3]}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

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

Analogues

• Butaperazine uses butanoyl (Butyryl) and not propanoyl group.
• Fluphenazine selfsame but trifluoromethyl on position 2 of the phenothiazine ring.

Notes and References

1. Book: Elks J . The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. 14 November 2014. Springer. 978-1-4757-2085-3. 224–.
2. Book: William Andrew Publishing. Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. 22 October 2013. Elsevier. 978-0-8155-1856-3. 862–.
3. Book: Briggs GG, Freeman RK, Yaffe SJ . Drugs in Pregnancy and Lactation: A Reference Guide to Fetal and Neonatal Risk. 2011. Lippincott Williams & Wilkins. 978-1-60831-708-0. 213–.