Perazine

Typical antipsychotic medication From Wikipedia, the free encyclopedia

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:

More information Summary, Outcome ...
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]
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Perazine
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • 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 Edit this at Wikidata
Chemical and physical data
FormulaC20H25N3S
Molar mass339.50 g·mol−1
3D model (JSmol)
  • CN1CCN(CC1)CCCN2C3=CC=CC=C3SC4=CC=CC=C42
  • 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
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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

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