Triflupromazine

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Triflupromazine
Triflupromazine.svg
Triflupromazine3d.png
Systematic (IUPAC) name
N,N-dimethyl-3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propan-1-amine
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
MedlinePlus a600010
Legal status
Identifiers
CAS number 146-54-3 YesY
ATC code N05AA05
PubChem CID 5568
IUPHAR ligand 4330
DrugBank DB00508
ChemSpider 5367 N
UNII RO16TQF95Y N
KEGG D00390 N
ChEBI CHEBI:9711 N
ChEMBL CHEMBL570 N
Chemical data
Formula C18H19F3N2S 
Mol. mass 352.418 g/mol
 N (what is this?)  (verify)

Triflupromazine (Vesprin) is an antipsychotic medication of the phenothiazine class. Among different effects of triflupromazine indication for use of this drug is severe emesis. Due to its potential side effects (triflupromazine has higher risk for side effects than many other antipsychotics) it is not gold standard in antiemetic therapy.

Serious side effects of trifluproamzine can be akathisia and tardive dyskinesia as well as the rare, but potentially fatal, neuroleptic malignant syndrome.

Chemistry[edit]

In an analogous manner to what has already been seen for the preparation of promazine and chlorpromazine, triflupromazine (2-trifluoromethyl-10-(3-dimethylaminopropyl) phenothiazine) is synthesized by the alkylation of 2-trifluoromethylphenothiazine using 3-dimethylaminopropylchloride in the presence of sodamide base.

  • J. Bernstein, F. Sowinski, DE 1095836  (1956).
  • G.E. Ullyot, U.S. Patent 2,921,069 (1960).
  • Smith Kline & French Lab., GB 813861  (1959).
  • B. Duhm, L. Koester, W. Maul, H. Medenwald, Z. Naturforsch., 13, 756 (1958).
  • Craig, P.; Nodiff, E.; Lafferty, J.; Ullyot, G. (1957). Journal of Organic Chemistry 22 (6): 709. doi:10.1021/jo01357a618.  edit
  • Yale, Harry L.; Sowinski, Francis; Bernstein, Jack (1957). "10-(3-Dimethylaminopropyl)-2-(Trifluoromethyl)-phenothiazine Hydrochloride (VESPRIN1) and Related Compounds. I". Journal of the American Chemical Society 79: 4375. doi:10.1021/ja01573a037.  edit

References[edit]