"Nitrosoguanidine" (N-methyl-N'-nitro-N-nitrosoguanidine) acts on polynucleotides in neutral aqueous solution, methylating guanine in the 7-position, and, to a much lesser extent, adenine. In 67 percent dimethylformamide the effect on the purines decreased, and what seems to be 3-methyl-cytosine appeared. In formamide solution no base changes were detected. Nitrosoguanidine had little mutagenic effect on tobacco mosaic virus RNA in water; it had greater effect in dimethylformamide, and even greater in formamide; it was a strong mutagen only when it acted on intact tobacco mosaic virus particles. Thus, neither the methylation of guanine nor the cytosine modification represents the main mutagenic event.
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