Quantitative gas chromatographic analysis of 3-cyano-3,3-diphenylpropionic acid, the acidic metabolite of bezitramide (Burgodin), in urine.
A sensitive gas chromatographic procedure with nitrogen-phosphorus detection was developed for the quantitative determination of 3-cyano-3,3-diphenylpropionic acid, the acidic metabolite of the narcotic analgesic bezitramide (Burgodin). Gas chromatography with mass spectrometric detection was used for confirmation. An internal standard, 5-cyano-5,5-diphenylvaleric acid, was synthesized and purified in our laboratory. The compound was extracted from 5 mL of hydrolyzed urine with n-hexane-ethyl acetate (85:15, v/v). Derivatization of the extract with an ethereal diazomethane solution was performed immediately before chromatographic analysis. Under the described conditions, the quantitation limit for 3-cyano-3, 3-diphenylpropionic acid in urine was 10 ng/mL. The extraction recovery was 82%. The calibration graph was linear over the concentration range from 10 to 500 ng/mL; at a 100-ng/mL concentration, within-day and day-to-day percent coefficients of variation of 1.9 and 3.7%, respectively, were obtained. Urine samples from 16 persons suspected of using bezitramide were analyzed, and they revealed metabolite concentrations that ranged from 10.5 to 88 ng/mL.
De Baere
S M
SM
Laboratorium voor Toxicologie, Universiteit Gent, Belgium.
Lambert
W E
WE
Van Bocxlaer
J F
JF
De Leenheer
A P
AP
D000085:Acetates / Q000737:chemistry; D000996:Antitussive Agents / Q000378:metabolism / Q000652:urine*; D001562:Benzimidazoles / Q000378:metabolism / Q000652:urine*; D002138:Calibration; D004347:Drug Interactions; D062787:Drug Overdose; D008401:Gas Chromatography-Mass Spectrometry; D006586:Hexanes / Q000737:chemistry; D006801:Humans; D013287:Illicit Drugs / Q000378:metabolism / Q000652:urine*; D009682:Magnetic Resonance Spectroscopy; D010666:Phenylpropionates / Q000652:urine; D011863:Radioimmunoassay; D012015:Reference Standards; D013055:Spectrophotometry, Infrared; D016320:Substance Abuse Treatment Centers
C101401:3-cyano-3,3-diphenylpropionic acid; D000085:Acetates; D000996:Antitussive Agents; D001562:Benzimidazoles; D006586:Hexanes; D013287:Illicit Drugs; D010666:Phenylpropionates; C026385:n-hexane; C004461:bezitramide; C007650:ethyl acetate