Butaperazine

Butaperazine (Repoise, Tyrylen) is a typical antipsychotic of the phenothiazine class.[1] It was approved in 1967, and possibly discontinued in the 1980s.

Butaperazine
Clinical data
ATC code
Identifiers
IUPAC name
  • 1-[10-[3-(4-methylpiperazin-1-yl)propyl]phenothiazin-2-yl]butan-1-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.010.450
Chemical and physical data
FormulaC24H31N3OS
Molar mass409.59 g·mol−1
3D model (JSmol)
SMILES
  • O=C(c2cc1N(c3c(Sc1cc2)cccc3)CCCN4CCN(C)CC4)CCC
InChI
  • InChI=1S/C24H31N3OS/c1-3-7-22(28)19-10-11-24-21(18-19)27(20-8-4-5-9-23(20)29-24)13-6-12-26-16-14-25(2)15-17-26/h4-5,8-11,18H,3,6-7,12-17H2,1-2H3 Y
  • Key:DVLBYTMYSMAKHP-UHFFFAOYSA-N Y
  (verify)

Synthesis
Patent:[2]

2-Butyrylphenothiazine [25244-91-1] (1) is the requisite starting material for carrying out the procedure. It is prepared in a manner that is synonymous with the method used in the propiomazine and propiopromazine already discussed. The 1-(γ-chloropropyl)-4-methylpiperazine [104-16-5] (2) is prepared in the conventional way from alkylating 1-methylpiperazine and 1-Bromo-3-chloropropane. Sodamide is used to extract the 10-H thereby facilitating the nucleophilic substitution reaction. And completing the instalment of the sidechain.

See also

References
  1. "Evaluation of a new antipsychotic agent. Butaperazine maleate (repoise maleate)". JAMA. 206 (10): 2307–8. December 1968. doi:10.1001/jama.206.10.2307. PMID 4386884.
  2. Dr Ulrich Hoerlein, Dr Klaus-Heinz Risse, Dr Wolfgang Wirth, DE 1120451 (1961 to Bayer Ag).
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