N-Nitrosamines by themselves are not signifi cant

Chapter 23, Problem 23.36

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N-Nitrosamines by themselves are not signifi cant carcinogens. However, they are activated in the liver by a class of iron-containing enzymes (members of the cytochrome P-450 family). Activation involves the oxidation of a C!H bond next to the amine nitrogen to a C!OH group. O O2 cyt P-450 H1 N-Nitrosopiperidine H N2 1 N"O OH N N"O N 2-Hydroxy-Nnitrosopiperidine An alkyl diazonium ion (a carcinogen) Show how this hydroxylation product can be transformed into an alkyl diazonium ion, an active alkylating agent and therefore a carcinogen, in the presence of an acid catalyst

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