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The Fate of 4-Cyanoacetanilide in Rats and Mice: The Mechanism of Formation of a Novel Electrophilic Metabolite

  • C. J. Logan
  • D. Hesk
  • D. H. Hutson
Part of the Advances in Experimental Medicine and Biology book series (AEMB, volume 197)

Abstract

4-Cyanoacetanilide (PCAA, b in Scheme 1) is a metabolite of 4-cyano-N,N-dimethyl-aniline (CDA, Scheme 1). Whilst the metabolism of CDA, a designed analogue of butter yellow (Ashby, Styles, Paton, 1980) was being investigated, a novel involvement of glutathione was detected (Hutson, Lakeman and Logan, 1984). From the structure of the mercapturic acid conjugate (C), which was isolated from the urine of the rats that had been dosed with CDA, it was postulated that the CDA had been de-methylated (A), acetylated (b), and that the methyl group of the acetyl group had been activated to form an electrophilic intermediate, the intermediate then being trapped, at least in part, by glutathione and eventually excreted as the mercapturic acid (C). interestingly, mice seemed to be unable to form this electrophilic intermediate.

Keywords

Mercapturic Acid Fast Atom Bombardment Mass Spectrometry Resultant Alcohol Amide Side Chain Magnetic Resonance Spectro 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. J. Ashby, J. A. Styles, and D. Paton, 1980, Carcinogenesis 1, 1.PubMedCrossRefGoogle Scholar
  2. S. Edwards, D. Hesk, C. J. Logan, and R. Waters, 1985, in: 2nd U. K. Environmental Mutagen Society Ring-Test, eds. C. Arlot, J. Ashby, and J. Parry. Pub. McMillan, London.Google Scholar
  3. D. H. Hutson, S. K. Lakeman, and C. J. Logan, 1984, Xenobiotica, 14, 925.PubMedCrossRefGoogle Scholar
  4. G. J. Mulder, and E. Scholtens, 1977, Biochem. J., 165, 553.PubMedGoogle Scholar

Copyright information

© Plenum Press, New York 1986

Authors and Affiliations

  • C. J. Logan
    • 1
  • D. Hesk
    • 1
  • D. H. Hutson
    • 2
  1. 1.Shell Development CompanyWesthollow Research CenterHoustonUSA
  2. 2.Shell Research LimitedSittingbourne Research CentreSittingbourne, KentUK

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