Metabolic Activation and Deactivation Mechanisms of Di-, Tri-, and Tetrachloroethylenes

  • D. Henschler
  • R. Hoos
Part of the Advances in Experimental Medicine and Biology book series (AEMB)


From a decade of intensive research in the metabolic transformation of chlorinated ethylenes, a general scheme of concurrent and subsequent reactions has evolved (Fig. 1):

Epoxides, formed by monooxygenases, may react by alkylating substitution with nucleophilic sites of macromolecules, e.g. with DNA (i); or rearrange, by intramolecular chlorine migration, to chlorinated aldehydes or acyl chlorides (ii); or be conjugated with glutathione, or cysteine, and subsequently be transformed, according to established metabolic pathways, to mercapturic acid derivatives (iii). Evidence for alkylation of DNA has been provided for vinyl chloride,1 vinylidene chloride,2 and trichloroethylene3,4 Rearrangement mechanisms have been studied in detail5 and found mostly consistent with the spectrum of metabolites found in vivo,6 and mercapturic acids have been demonstrated as the main metabolites of vinyl and vinylidene chlorides.7,8,9,10,11


Vinyl Chloride Vinylidene Chloride Chloroacetic Acid Acyl Chloride Glyoxylic Acid 
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Copyright information

© Springer Science+Business Media New York 1982

Authors and Affiliations

  • D. Henschler
    • 1
  • R. Hoos
    • 1
  1. 1.Institute of ToxicologyUniversity of WürzburgWürzburgGermany

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