Perazine

Typical antipsychotic medication
  • N05AB10 (WHO)
Identifiers
  • 10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine
CAS Number
  • 84-97-9 checkY
PubChem CID
  • 4744
DrugBank
  • DB12710 checkY
ChemSpider
  • 4582 ☒N
UNII
  • 8915147A2B
KEGG
  • C16903
ChEBI
  • CHEBI:59118 ☒N
ChEMBL
  • ChEMBL1697766
CompTox Dashboard (EPA)
  • DTXSID6048628 Edit this at Wikidata
ECHA InfoCard100.001.435 Edit this at WikidataChemical and physical dataFormulaC20H25N3SMolar mass339.50 g·mol−13D model (JSmol)
  • Interactive image
  • 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
 ☒NcheckY (what is this?)  (verify)

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]
Outcome Findings in words Findings in numbers Quality of evidence
Global state
No better or deterioration
Follow-up: average 5 weeks
Perazine may decrease the chance of experiencing this outcome. These findings are based on data of low quality. RR 0.43 (0.23 to 0.81) Low
Mental state
Less than 30% BPRS reduction
Follow-up: mean 5 weeks
The average overall mental state score in the perazine group was lower than for those given other antipsychotic drugs but the difference between the groups was not clear. These findings are based on data of low quality. RR 0.82 (0.61 to 1.09) Low
Adverse effects
Needing antiparkinson medication
Follow-up: average 5 weeks
Perazine might increase the risk of experiencing this outcome but at present it is not possible to be confident about the difference between perazine and other antipsychotic drugs. Data supporting this finding are very limited. RR 4.5 (1.04 to 19.45) Very low
Leaving the study early - due to adverse events
Follow-up: average 4 weeks
There was not a clear difference between perazine and the other antipsychotic drugs for this general outcome reflecting overall adverse event 'load'. These findings are based on data of low quality. 0.87 (0.4 to 1.9) Low
Acceptability of treatment
Leaving the studies early - any reason
Follow-up: 5 weeks
Perazine and the comparison antipsychotic drugs were equally tolerated. These findings are based on data of low quality. RR 0.62 (0.35 to 1.1) Low
No study reported any data on outcomes such as quality of life or information relating to satisfaction with care.

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. ^ a b 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. PMC 11015532. 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.

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