Trifluperidol

Trifluperidol

Systematic (IUPAC) name
1-(4-fluorophenyl)-4-[4-hydroxy-4-[3-(trifluoromethyl)phenyl]piperidin-1-yl]butan-1-one
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
Identifiers
CAS Number	749-13-3 N
ATC code	N05AD02 (WHO)
PubChem	CID: 5567
ChemSpider	5366 Y
UNII	R8869Q7R8I Y
ChEMBL	CHEMBL15023 Y
Chemical data
Formula	C22H23F4NO2
Molecular mass	409.417 g/mol
SMILES FC(F)(F)c1cccc(c1)C3(O)CCN(CCCC(=O)c2ccc(F)cc2)CC3
InChI InChI=1S/C22H23F4NO2/c23-19-8-6-16(7-9-19)20(28)5-2-12-27-13-10-21(29,11-14-27)17-3-1-4-18(15-17)22(24,25)26/h1,3-4,6-9,15,29H,2,5,10-14H2 Y Key:GPMXUUPHFNMNDH-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Trifluperidol is a typical antipsychotic of the butyrophenone chemical class. It has general properties similar to those of haloperidol, but is considerably more potent by weight, and causes relatively more severe side effects, especially tardive dyskinesia and other extrapyramidal effects. It is used in the treatment of psychoses including mania and schizophrenia. It was discovered at Janssen Pharmaceutica in 1959.

Synthesis

Trifluperidol Synthesis: P. Janssen, J. Adriaan, GB 895309  (1962), U.S. Patent 3,438,991 (1969).

References

• Gallant DM, Bishop MP, Timmons E, Steele CA, A controlled evaluation of Trifluperidol: a new potent psychopharmacologic agent, Curr Ther Res Clin Exp. 1963 Sep;27:463-71.
• Gallant DM, Bishop MP, Timmons E, Steele CA, Trifluperidol: a butyrophenone derivative, Am J Psychiatry. 1963 Nov;120:485-7.