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Science 28 September 1973:
Vol. 181. no. 4106, pp. 1245 - 1247
DOI: 10.1126/science.181.4106.1245
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Articles

N-Nitrosation by Nitrite Ion in Neutral and Basic Medium

Larry K. Keeper 1 and Peter P. Roller 1

1 Division of Cancer Cause and Prevention, National Cancer Institute, Bethesda, Maryland 20014

Formaldehyde catalyzed the conversion of various secondary amines to nitrosamines in the pH range 6.4 to 11.0. Chloral was also an effective catalyst. The reaction proceeds easily enough to have potential synthetic applications; the proposed mechanism could explain some reported anomalies regarding the synthesis of carcinogenic N-nitroso compounds in vivo and in vitro.


THIS ARTICLE HAS BEEN CITED BY OTHER ARTICLES:
N'-Nitrosonornicotine in Tobacco.
D. Hoffmann, S. S. Hecht, R. M. Ornaf, and E. L. Wynder (1974)
Science 186, 265-267
   Abstract »    PDF »
2'-Hydroxylation of nicotine by cytochrome P450 2A6 and human liver microsomes: Formation of a lung carcinogen precursor.
S. S. Hecht, J. B. Hochalter, P. W. Villalta, and S. E. Murphy (2000)
PNAS 97, 12493-12497
   Abstract »    Full Text »    PDF »


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Science. ISSN 0036-8075 (print), 1095-9203 (online)