Mechanism of formation of mercapturic acids from (1-bromoethyl)benzene and (2-bromoethyl)benzene in the rat.
1. Three hypotheses have been proposed for the mechanism of metabolism of alkylhalides to hydroxy-alkylmercapturic acids, two of which involve the intermediate step of dehydrohalogenation and formation of an epoxide. 2. After injection of (1-bromoethyl)benzene in rat, the only mercapturic acid appearing in the urine was N-acetyl-S-1-phenylethylcysteine. After injecting (2-bromoethyl)benzene in the rat only N-acetyl-S-2-phenylethylcysteine and N-acetyl-S-(2-phenyl-2-hydroxyethyl)cysteine were found in the urine. 3. Since the principal mercapturic acid formed from both styrene and styrene oxide could not be detected in the urine of rats receiving either 1- or 2-bromoethyl benzene, the intermediate formation of styrene or styrene oxide from the arylalkylhalides does not occur.
D000111:Acetylcysteine / Q000378:metabolism* / Q000652:urine; D000818:Animals; D001711:Biotransformation; D005260:Female; D006842:Hydrocarbons, Brominated / Q000378:metabolism*; D051381:Rats
D006842:Hydrocarbons, Brominated; C021638:(2-bromoethyl)benzene; C021637:(1-bromoethyl)benzene; D000111:Acetylcysteine