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Premercapturic acid metabolites of bromobenzene derived via its 2,3- and 3,4-oxide metabolites.

Abstract
1. A new premercapturic acid metabolite of bromobenzene was isolated from the urine of beta-naphthoflavone-induced rats; using 1H-n.m.r., FAB mass spectrometry and chemical degradation it was identified as S-(2-hydroxy-3-bromocyclohexa-3,5-dienyl)-N-acetylcysteine. 2. Two regioisomeric premercapturic acids apparently derived from bromobenzene-3,4-oxide were isolated as an inseparable 1:1 mixture from the urine of phenobarbital-induced rats and characterized by similar means. 3. Acid dehydration of bromobenzene 3,4- and 4,3-premercapturic acids (mixture) afforded only p-bromophenylmercapturic acid, whereas acid dehydration of 3,2-premercapturic acid gave both o- and m-bromophenylmercapturic acids. This implies a shift of sulphur in acid dehydration of the 3,4- and 3,2- but not the 4,3-premercapturic acids. 4. Base dehydration of the 3,4- and 4,3-premercapturic acid mixture gave a mixture of p- and m-bromophenylmercapturic acids, whereas base dehydration of the 3,2-premercapturic acid gave only m-bromophenylmercapturic acid. This indicates these premercapturic acids dehydrate by direct elimination without rearrangment. 5. The 3,2-premercapturic acid was detected only in the urine of BNF-induced animals, whereas the 3,4- and 4,3-premercapturic acids were detected in the urines of untreated as well as PB- and BNF-induced animals. 6. Together with earlier reports of the isolation of the 2,3-dihydrodiol, the isolation of the 3,2-premercapturic acid as a urinary metabolite of bromobenzene implies that bromobenzene-2,3-oxide is a discrete metabolite of bromobenzene and not merely a hypothetical intermediate.
AuthorsJ Zheng, R P Hanzlik
JournalXenobiotica; the fate of foreign compounds in biological systems (Xenobiotica) Vol. 21 Issue 4 Pg. 535-46 (Apr 1991) ISSN: 0049-8254 [Print] England
PMID1897252 (Publication Type: Journal Article, Research Support, U.S. Gov't, P.H.S.)
Chemical References
  • Bromobenzenes
  • Water
  • 3,4-premercapturic acid
  • 3,2-premercapturic acid
  • 4,3-premercapturic acid
  • bromobenzene
  • Acetylcysteine
Topics
  • Acetylcysteine (analogs & derivatives, metabolism, urine)
  • Animals
  • Bromobenzenes (metabolism)
  • Chromatography, High Pressure Liquid
  • Hydrogen-Ion Concentration
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Rats
  • Water (chemistry)

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