Mutagenic and alkylating activities of 3-methyl-1-phenyltriazenes and their possible role as carcinogenic metabolites of the parent dimethyl compounds.

3-Methyl-1-phenyltriazene and a series of ring-substituted derivatives (4-methylphenyl, 4-chlorophenyl, and 2,4,6-trichlorophenyl), structurally related benzenediazonium fluoborates and phenyl azides, as well as the recently isolated [1-methyl-3-(2,4,6-trichlorophenyl)-2-triazeno]methyl-beta-D-glucopyranoside uronic acid, were studied for their mutagenic activity in Salmonella typhimurium strains. Of these compounds, the 3-methyl-1-phenyltriazene derivatives and 2,4,6-trichlorobenzenediazonium fluoborate were found to be direct-acting mutagens; the glucuronide was active in strain TA 1530 only after deconjugation with beta-glucuronidase. The half-lives of the monomethylphenyltriazenes in vitro were determined and compared with their methylating activity towards 4-(4-nitrobenzyl)pyridine and their mutagenicity. The results are discussed in relation to the possible mechanism of action of the N,N-dimethylphenyltriazenes and their monomethyl derivatives as mutagens and organ-specific carcinogens.