Fluanisone

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Fluanisone
Fluanisone.svg
Systematic (IUPAC) name
1-(4-fluorophenyl)-4-[4-(2-methoxyphenyl)piperazin-1-yl]butan-1-one
Identifiers
ATC code N05AD09 (WHO)
PubChem CID 15139
ChemSpider 14410 YesY
UNII 1D0W98U1I4 YesY
KEGG D02621 YesY
ChEMBL CHEMBL58792 YesY
Chemical data
Formula C21H25FN2O2
Molar mass 356.43 g/mol
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Fluanisone is a typical antipsychotic and sedative of the butyrophenone chemical class. It is used in the treatment of schizophrenia and mania. A fentanyl/fluanisone combination can be used to produce a so-called neuroleptanalgesic.

Synthesis[edit]

Fluanisone synthesis: Paul Adriaan J. Janssen; U.S. Patent 2,997,472 (1961).

Treatment of a mixture of o-Anisidine and Diethanolamine with hydrogen chloride affords the aryl-substituted piperazine, #. (The first step in this reaction probably consists in conversion of at least one hydroxyl group to the chloride; this then serves to alkylate the aromatic amine.) Alkylation of the secondary nitrogen with 4-chloro-p-fluorobutyrophenone (obtained by acylation of fluorobenzene with 4-chlorobutyryl chloride) gives the ataractic agent fluanisone.

See also[edit]

  • Zoloperone is another drug that is prepared from the 1-(2-methoxyphenyl)piperazine.

References[edit]