2,7-Diamino-3,8-dimethylphenazine as the major mutagenic product from the reaction of 2,4-diaminotoluene with hydrogen peroxide.
The mutagenicity of 2,4-diaminotoluene (DAT) in Ames's Salmonella/microsome test was remarkably enhanced by treatment with hydrogen peroxide. Therefore, identification of the major mutagenic reaction product of 2,4-DAT with hydrogen peroxide at room temperature has been performed. Red precipitates were produced in a 2-day reaction mixture and were column chromatographed on silica gel. 5 fractions having mutagenic potency were obtained. The red crystalline needles, obtained as the major reaction product, were separated from fraction 2 and were subjected to high resolution mass spectrometry, 1H- and 13C-NMR spectrometry. The structure of the compound was determined to be 2,7-diamino-3,8-dimethylphenazine from physicochemical and chemical evidence. The compound induced 212 revertants/nmole in Salmonella typhimurium TA98 with 25 microliters S9 per plate.
D000818:Animals; D001711:Biotransformation; D006861:Hydrogen Peroxide / Q000378:metabolism*; D008297:Male; D008862:Microsomes, Liver / Q000378:metabolism; D010619:Phenazines / Q000138:chemical synthesis / Q000302:isolation & purification* / Q000494:pharmacology; D010655:Phenylenediamines / Q000378:metabolism*; D051381:Rats; D011919:Rats, Inbred Strains; D012486:Salmonella typhimurium / Q000187:drug effects
D010619:Phenazines; D010655:Phenylenediamines; C051441:2,7-diamino-3,8-dimethylphenazine; D006861:Hydrogen Peroxide; C010914:2,4-diaminotoluene