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Reaction of Drugs with Nitrous Acid as a Source of Carcinogenic Nitrosamines¹

Carcinogenesis Program, Biology Division, Oak Ridge National Laboratory, Oak Ridge, Tennessee 37830

Twelve common drugs that are tertiary amines react with nitrite in aqueous solution at ph 3 to 4 to form dialkylnitrosamines that are known carcinogens. Aminopyrine gave dimethylnitrosamine in 30% yield or higher at all concentrations down to 50 ppm (with 25 ppm nitrite); the other product of this reaction was the nitrite salt of 4-hydroxyantipyrine. The other drugs, when present at 0.01 M with 0.04 M nitrite, formed nitrosamines in yields ranging from 0.03% from dextropoxyphene to 2.4% from lucanthone in 4 hr at 37°.

¹ Research jointly sponsored by the National Cancer Institute and the United States Atomic Energy Commission under contract with Union Carbide Corporation.

Received 6/21/73. Accepted 9/24/73.

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