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Potential metabolic mutagens of caffeine and various methylxanthines.

Authors
  • Lander, N
  • Soloway, A H
  • Minton, J P
  • Rawal, B D
  • Gairola, C C
Type
Published Article
Journal
Journal of pharmaceutical sciences
Publication Date
Nov 01, 1988
Volume
77
Issue
11
Pages
955–958
Identifiers
PMID: 3225757
Source
Medline
License
Unknown

Abstract

Xanthine N-carbinols, potential metabolites of caffeine and other methylxanthines, have been synthesized, characterized, and derivatized. Such intermediates, the initial metabolites arising from the cytochrome P-450 oxidation of the nitrogen-bound methyl groups, may be viewed as biological N-carbinols capable of alkylating proteins and nucleic acids. Evaluation of these compounds against Salmonella typhimurium, strain TA100, has demonstrated that, in contrast to caffeine, 7-hydroxymethyltheophylline and the 3,7-bis(hydroxymethyl)-1-methylxanthine mixture did exhibit cytotoxicity. There was no evidence of mutagenesis and it is possible that the Ames assay system is not applicable to N-carbinols.

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