Perazine

Perazine (Taxilan) is a moderate-potency typical antipsychotic of the phenothiazine class. It is quite similar to chlorpromazine, and acts as a dopamine antagonist. A 2014 systematic review compared it with other antipsychotic drugs:

Perazine versus other antipsychotic drugs for schizophrenia[1]
Summary
The number, size and reporting of randomized controlled perazine trials are insufficient to present firm conclusions about the properties of this antipsychotic. It is possible that perazine is associated with a similar risk of extrapyramidal side effects as some atypical antipsychotics but this is based on few comparisons of limited power.[1]
Perazine
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
IUPAC name
  • 10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.435
Chemical and physical data
FormulaC20H25N3S
Molar mass339.50 g·mol−1
3D model (JSmol)
SMILES
  • CN1CCN(CC1)CCCN2C3=CC=CC=C3SC4=CC=CC=C42
InChI
  • InChI=1S/C20H25N3S/c1-21-13-15-22(16-14-21)11-6-12-23-17-7-2-4-9-19(17)24-20-10-5-3-8-18(20)23/h2-5,7-10H,6,11-16H2,1H3 N
  • Key:WEYVCQFUGFRXOM-UHFFFAOYSA-N N
 NY (what is this?)  (verify)

Synthesis
Perazine synthesis:[2][3] Patents:[4][5] Alternate source:[6][7]

Phenothiazine-10-propionitrile [1698-80-2] (1) is treated with a mixture of acid and alcohol giving Methyl phenothiazinepropionate, CID:368244 (2). Heating with 1-methylpiperazine (3) gives the amide [91508-47-3] (4). Reduction of this last by means of diborane yields Perazine (5).

See also

References
  1. Leucht S, Helfer B, Hartung B (January 2014). "Perazine for schizophrenia". The Cochrane Database of Systematic Reviews. 1 (1): CD002832. doi:10.1002/14651858.CD002832.pub3. PMID 24425538.
  2. Hromatka, O.; Sauter, F.; Schlager, L. H. (1957). "Untersuchungen über Phenthiazinderivate III: Über die Synthese von 10-(Piperazinoalkyl)-phenthiazinen". Monatshefte für Chemie. 88 (2): 193–201. doi:10.1007/BF00901625.
  3. Hromatka, O.; Stehlik, G.; Sauter, F. (1960). "Untersuchungen über Phenthiazinderivate, 12. Mitt.: Reaktionen zur Géwinnung von 10-(?-Methylpiperazinylpropyl)-phenthiazin". Monatshefte für Chemie 91 (1): 107–116. doi:10.1007/BF00903173.
  4. GB780193 idem Horclois Raymond Jacques, U.S. Patent 2,902,485 (1957 to Rhône-Poulenc).
  5. Anon., GB 901187 (1962 to Chemische Fabrik Promonta GmbH).
  6. Owen, Terence C. (1984). "Synthesis of perazine". Journal of Heterocyclic Chemistry. 21 (1): 265–266. doi:10.1002/jhet.5570210154.
  7. Brufani; Cesta; Filocamo; Lappa; Marta; Pomponi; Meroni; Pagella Farmaco, 1992 , vol. 47, # 5 p. 585 – 597.
  • Perazine at the US National Library of Medicine Medical Subject Headings (MeSH)
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