Synthesis of deuterium‐labeled nitrosomethylethylamines

Mangino, Mario M.; Lijinsky, William; Singer, George M.

doi:10.1002/jlcr.2580140507

Labelled Comp Radiopharmac

1978

DOI: 10.1002/jlcr.2580140507

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Synthesis of deuterium‐labeled nitrosomethylethylamines

Mario M. Mangino

William Lijinsky

George M. Singer

Abstract: SUMMARYE thy1 isocyanate, N-methyl acetami de , !-methy lacetami d e -a , and 1-methylacetamide-& were reduced w i t h l i t h i u m aluminum deut e r i d e and then n i t r o s a t e d w i t h sodium n i t r i t e t

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Cited by 3 publications

References 7 publications

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Deuterium isotope effects in carcinogenesis by N-nitroso compounds

Lijinsky

1986

J Cancer Res Clin Oncol

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A number of N-nitroso compounds and an azoxyalkane have been labeled with deuterium in various positions and have been administered to rats, hamsters, or mice in parallel with the unlabeled compounds. The treatments with the labeled and analogous unlabeled compounds were equimolar and for the same time. Mortality rates from tumors and tumor incidences were compared between deuterium-labeled and the unlabeled analogs. In many cases more than one dose level was used for the comparisons. An increased rate of mortality from tumors or an increased incidence of induced tumors was considered an index of increased potency of one treatment compared with the other. Using these criteria deuterium in the alpha positions of nitrosodimethylamine, nitrosomorpholine, nitrosoheptamethyleneimine, and nitrosoazetidine reduced carcinogenic potency compared with the unlabeled compounds. This indicated that cleavage of a carbon-hydrogen bond in the alpha position was a rate-limiting step in carcinogenesis by these nitrosamines. In both nitrosomethylethylamine and nitroso-2,6-dimethylmorpholine, the presence of deuterium at different positions increased or decreased carcinogenic potency, suggesting that competition for oxidation between these sites might be the determining factor in activation of the molecule. This also applied to nitrosomethyl-n-butylamine and nitrosomethyl-phenylethylamine with deuterium at the methyl group or at the alpha carbon of the butyl or phenylethyl groups, and to azoxymethane with deuterium in the 1-methyl or 4-methyl group. In nitrosomethylcyclohexylamine, nitrosomethyl-n-dodecylamine, and dinitroso-2,6-dimethylpiperazine there was no detectable effect of deuterium on carcinogenic potency, suggesting that the conditions did not provide sufficient sensitivity for detection of an isotope effect, or that oxidation at the alpha carbon was not a rate-limiting step in carcinogenesis by these molecules.

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Deuterium isotope effects in carcinogenesis by N-nitroso compounds

Lijinsky

1986

J Cancer Res Clin Oncol

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Relative extents of hydrogen-deuterium exchange of nitrosamines: Relevance to biological isotope effect studies

Singer

Lijinsky

1979

Cancer Letters

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β-Ketonitrosamines. Synthetic Equivalents of α-Methylene Alkylamino Anions (⁻CH₂NHR)

Saavedra

Farnsworth

Farrelly

1989

Synthetic Communications

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Synthesis of deuterium‐labeled nitrosomethylethylamines

Abstract: SUMMARYE thy1 isocyanate, N-methyl acetami de , !-methy lacetami d e -a , and 1-methylacetamide-& were reduced w i t h l i t h i u m aluminum deut e r i d e and then n i t r o s a t e d w i t h sodium n i t r i t e t

Cited by 3 publications

References 7 publications

Deuterium isotope effects in carcinogenesis by N-nitroso compounds

Deuterium isotope effects in carcinogenesis by N-nitroso compounds

Relative extents of hydrogen-deuterium exchange of nitrosamines: Relevance to biological isotope effect studies

β-Ketonitrosamines. Synthetic Equivalents of α-Methylene Alkylamino Anions (⁻CH₂NHR)

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Synthesis of deuterium‐labeled nitrosomethylethylamines

Abstract: SUMMARYE thy1 isocyanate, N-methyl acetami de , !-methy lacetami d e -a , and 1-methylacetamide-& were reduced w i t h l i t h i u m aluminum deut e r i d e and then n i t r o s a t e d w i t h sodium n i t r i t e t

Cited by 3 publications

References 7 publications

Deuterium isotope effects in carcinogenesis by N-nitroso compounds

Deuterium isotope effects in carcinogenesis by N-nitroso compounds

Relative extents of hydrogen-deuterium exchange of nitrosamines: Relevance to biological isotope effect studies

β-Ketonitrosamines. Synthetic Equivalents of α-Methylene Alkylamino Anions (−CH2NHR)

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Product

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β-Ketonitrosamines. Synthetic Equivalents of α-Methylene Alkylamino Anions (⁻CH₂NHR)