Synthesis of deuterium-labeled fluphenazine

Journal Article · Sat Dec 31 23:00:00 EST 1983 · J. Pharm. Sci.; (United States)

DOI:https://doi.org/10.1002/jps.2600730123· OSTI ID:6826846

Shetty, H U; Hawes, E M; Midha, K K

The propylpiperazine side chain of fluphenazine has been labeled with two, four, and six deuterium atoms by lithium aluminum deuteride reduction of the appropriate ester or imide. The gamma-carbon of the propyl group was labeled with two deuterium atoms by reduction of 10- (2-methoxycarbonylethyl) -2-trifluoromethyl-10H-phenothiazine, while four deuterium atoms were incorporated into the piperazine ring by reduction of 10-(3-(3,5-dioxo-1-piperazinyl)propyl)-2-trifluoromethyl-10H-pheno thiazine. The latter reduction gave the d4-labeled N-deshydroxyethyl metabolite of fluphenazine.

• Research Organization: Univ. of Saskatchewan, Saskatoon, Canada
• OSTI ID: 6826846
• Journal Information: J. Pharm. Sci.; (United States), Journal Name: J. Pharm. Sci.; (United States) Vol. 73:1; ISSN JPMSA
• Country of Publication: United States
• Language: English

Related Subjects

38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
400702* -- Radiochemistry & Nuclear Chemistry-- Properties of Radioactive Materials
AZINES
CHEMICAL PREPARATION
CHEMICAL REACTIONS
CHEMISTRY
DEUTERATION
DEUTERIUM COMPOUNDS
DRUGS
HETEROCYCLIC COMPOUNDS
HYDROGEN COMPOUNDS
LABELLED COMPOUNDS
LABELLING
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PHENAZINE
PYRAZINES
RADIATION CHEMISTRY
RADIOPHARMACEUTICALS
SYNTHESIS