Chemical oxidation and metabolism of N-methyl-N-formylhydrazine. Evidence for diazenium and radical intermediates

P. M. Gannett, C. Garrett, Terence A Lawson, B. Toth

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

N-Methyl N-formylhydrazine (1), a component of the mushroom Gyromitra esculenta, is a carcinogen. Its mode of action, however, is poorly understood. To determine the intermediates that may form during the metabolism of 1, we examined its oxidative chemistry, identified the products and inferred the intermediates on the basis of these products. The incubation of 1 with rat liver microsomes was also studied and the metabolites determined and quantified. Both the chemical and the microsome-mediated oxidation of 1 yielded formaldehyde and acetaldehyde. The formation of acetaldehyde requires (i) the oxidation of 1 to a diazenium ion (I) or diazene (II) and (ii) fragmentation of I/II to formyl and methyl radicals. It is suggested that these radical intermediates may be important in understanding and elucidating carcinogenesis by 1.

Original languageEnglish (US)
Pages (from-to)49-56
Number of pages8
JournalFood and Chemical Toxicology
Volume29
Issue number1
DOIs
StatePublished - Jan 1 1991

Fingerprint

Acetaldehyde
acetaldehyde
Metabolism
Gyromitra esculenta
oxidation
Oxidation
liver microsomes
metabolism
Agaricales
microsomes
Liver Microsomes
carcinogens
Metabolites
Microsomes
formaldehyde
Carcinogens
Liver
mushrooms
carcinogenesis
Formaldehyde

ASJC Scopus subject areas

  • Food Science
  • Toxicology

Cite this

Chemical oxidation and metabolism of N-methyl-N-formylhydrazine. Evidence for diazenium and radical intermediates. / Gannett, P. M.; Garrett, C.; Lawson, Terence A; Toth, B.

In: Food and Chemical Toxicology, Vol. 29, No. 1, 01.01.1991, p. 49-56.

Research output: Contribution to journalArticle

Gannett, P. M. ; Garrett, C. ; Lawson, Terence A ; Toth, B. / Chemical oxidation and metabolism of N-methyl-N-formylhydrazine. Evidence for diazenium and radical intermediates. In: Food and Chemical Toxicology. 1991 ; Vol. 29, No. 1. pp. 49-56.
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