Perazine Explained

Verifiedfields:changed
Watchedfields:changed
Verifiedrevid:444044065
Atc Prefix:N05
Atc Suffix:AB10
Cas Number:84-97-9
Pubchem:4744
Drugbank:DB12710
Chemspiderid:4582
Unii:8915147A2B
Kegg:C16903
Chebi:59118
Chembl:1697766
Iupac Name:10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine
C:20
H:25
N:3
S:1
Smiles:CN1CCN(CC1)CCCN2C3=CC=CC=C3SC4=CC=CC=C42
Stdinchi: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
Stdinchikey:WEYVCQFUGFRXOM-UHFFFAOYSA-N

Perazine (Taxilan) is a moderate-potency typical antipsychotic of the phenothiazine class. It is quite similar to chlorpromazine, and acts as a dopamine antagonist. It was very popular in West-Germany. 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.

Synthesis

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

Notes and References

  1. Leucht S, Helfer B, Hartung B . Perazine for schizophrenia . The Cochrane Database of Systematic Reviews . 1 . 1 . CD002832 . January 2014 . 24425538 . 10.1002/14651858.CD002832.pub3 . 11015532 .