Triflupromazine

Triflupromazine

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	℞-only (US)
Identifiers
CAS number	146-54-3 Y
ATC code	N05AA05
PubChem	CID 5568
IUPHAR ligand	4330
DrugBank	DB00508
ChemSpider	5367 N
UNII	RO16TQF95Y N
KEGG	D00390 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

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. 
• 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. 

References