N-Nitrosamines by themselves are not significant 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. OH ОН N=0 N=O Og 'N- H+ H N,+ cyt P-450 N-Nitroso- 2-Нydroxy-N- nitrosopiperidine An alkyl diazonium ion piperidine (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.

Chemistry by OpenStax (2015-05-04)
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Chapter12: Kinetics
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N-Nitrosamines by themselves are not significant 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.
OH
ОН
N=0
N=O
Og
'N-
H+
H
N,+
cyt P-450
N-Nitroso-
2-Нydroxy-N-
nitrosopiperidine
An alkyl diazonium ion
piperidine
(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.
Transcribed Image Text:N-Nitrosamines by themselves are not significant 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. OH ОН N=0 N=O Og 'N- H+ H N,+ cyt P-450 N-Nitroso- 2-Нydroxy-N- nitrosopiperidine An alkyl diazonium ion piperidine (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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