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Penfluridol

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Penfluridol Basic information
Penfluridol Chemical Properties
  • Melting point:105-107°C
  • Boiling point:587.7±50.0 °C(Predicted)
  • Density 1.2425 (estimate)
  • storage temp. 2-8°C
  • solubility H2O: insoluble
  • form powder
  • pka13.49±0.20(Predicted)
  • color white
  • Merck 14,7087
  • CAS DataBase Reference26864-56-2(CAS DataBase Reference)
  • NIST Chemistry ReferencePenfluridol(26864-56-2)
Safety Information
  • Hazard Codes T
  • Risk Statements 25
  • Safety Statements 45
  • RIDADR UN 2811 6.1/PG 3
  • WGK Germany 3
  • RTECS TN6957000
  • HazardClass 6.1
  • PackingGroup III
  • HS Code 29333990
  • ToxicityLD50 orally in mice (day 7): 86.8 mg/kg (Janssen)
MSDS
Penfluridol Usage And Synthesis
  • OriginatorSemap,Janssen-Le Brun ,W. Germany ,1975
  • Usesantineoplastic
  • UsesIn terms of pharmacological action, penfluridol is similar to pimozide; however, it is significantly longer lasting, which is connected to the slow metabolism of the drug. Penfluridol is used as a supportive therapy in ambulatory settings for patients suffering from schizophrenia as well as patients with paranoid, psychotic, and neuroleptic conditions.
  • Manufacturing ProcessA mixture of 24 parts of 4,4-bis(p-fluorophenyl)butyl chloride, 20.9 parts of 4(4-chloro-α,α,α-trifluoro-m-tolyl)-4-piperidinol, 13.8 parts of sodium carbonate, a few crystals of potassium iodide in 600 parts of 4-methyl-2pentanone is stirred and refluxed for 60 hours. The reaction mixture is cooled and 150 parts of water is added. The organic layer is separated, dried, filtered and evaporated. The oily residue is crystallized from diisopropylether, yielding 4-(4chloro-α,α,α-trifluoro-m-tolyl)-1-[4,4-bis(p-fiuorophenyl)butyl]-4piperidinol; melting point 106.5°C.
  • brand nameSemap (Ortho-McNeil).
  • Therapeutic Function Antipsychotic
  • Safety ProfilePoison by ingestion and intravenous routes. Experimental teratogenic and reproductive effects. A neuroleptic agent. When heated to decomposition it emits very toxic fumes of Cl-, F-, and NOx.
  • Chemical SynthesisPenfluridol, 4-(4-chloro-3-trifluoromethylphenyl)-1-[4,4-bis-(p-fluorophenyl) butyl]-4-piperidinol (6.6.12), is synthesized implementing a Grignard reaction between 1-carbomethoxypiperidin-4-one and 4-chloro-3-trifluoromethylphenylmagnesium bromide, giving 1-carbomethoxy-(4-chloro-3-trifluoromethylphenyl)-4-piperidinol (6.6.10). Upon alkaline hydrolysis of the carbomethoxy group, it turns into (4-chloro-3-trifluoromethylphenyl)-4-piperidinol (6.6.11), the alkylation of which with 1,1-bis(4-fluorophenyl)butyl bromide (6.6.3) gives penfluridol (6.6.12) [67–69].

Penfluridol Preparation Products And Raw materials
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