Synthesis of carbon‐14 labeled 4‐(methylnitrosamino)‐1‐(3‐pyridyl)‐1‐butanone
- 1 January 1985
- journal article
- research article
- Published by Wiley in Journal of Labelled Compounds and Radiopharmaceuticals
- Vol. 22 (1) , 23-28
- https://doi.org/10.1002/jlcr.2580220104
Abstract
The potent carcinogen 4‐(methylnitrosamino)‐1‐(3‐pyridyl)‐1‐butanone (NNK) is present in tobacco and tobacco smoke. [Carbonyl14C]NNK (6) was synthesized in 27% overall yield. [Carboxyl‐14C] nicotinic acid (1) was esterified with benzyl alcohol and the ester 2 was alkylated by 3‐lithio‐N‐methylpyrrolidin‐2‐one (3). The resulting keto‐lactam 4 was hydrolyzed and decarboxylated by treatment with boiling hydrochloric acid. Nitrosation at pH 4.0 gave [carbonyl‐14C]NNK (6). Carbonyl reduction of [carbonyl‐14C]NNK with either sodium borohydride or cultured rat liver slices gave [carbinol‐14C] 4‐(methylnitrosamino)‐1‐(3‐pyridyl) butan‐1‐ol‐(7).Keywords
This publication has 11 references indexed in Scilit:
- Metabolism of tobacco-specific N-nitrosamines by cultured human tissues.Proceedings of the National Academy of Sciences, 1983
- Effects of α-deuterium substitution on the mutagenicity of 4-(methyl-nitrosamino)-1-(3-pyridyl)-1-butanone (NNK)1Carcinogenesis: Integrative Cancer Research, 1983
- A STUDY OF CHEMICAL CARCINOGENESIS .45. COMPARATIVE CARCINOGENICITY IN A/J MICE AND METABOLISM BY CULTURED MOUSE PERIPHERAL LUNG OF N'-NITROSONORNICOTINE, 4-(METHYLNITROSAMINO)-1-(3-PYRIDYL)-1-BUTANONE, AND THEIR ANALOGS1983
- TISSUE DISTRIBUTION OF THE TOBACCO-SPECIFIC CARCINOGEN 4-(METHYLNITROSAMINO)-1-(3-PYRIDYL)-1-BUTANONE AND ITS METABOLITES IN F344 RATS1983
- On the formation of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone during smoking☆Cancer Letters, 1983
- A STUDY OF TOBACCO CARCINOGENESIS .23. CARCINOGENIC TOBACCO-SPECIFIC N-NITROSAMINES IN SNUFF AND IN THE SALIVA OF SNUFF DIPPERS1981
- A STUDY ON TOBACCO CARCINOGENESIS .20. COMPARATIVE CARCINOGENICITY AND METABOLISM OF 4-(METHYLNITROSAMINO)-1-(3-PYRIDYL)-1-BUTANONE AND N'-NITROSONORNICOTINE IN SYRIAN GOLDEN-HAMSTERS1981
- STUDY OF TOBACCO CARCINOGENESIS .19. COMPARATIVE CARCINOGENICITY IN F344 RATS OF THE TOBACCO-SPECIFIC NITROSAMINES, N'-NITROSONORNICOTINE AND 4-(N-METHYL-N-NITROSAMINO)-1-(3-PYRIDYL)-1-BUTANONE1980
- A STUDY OF CHEMICAL CARCINOGENESIS .31. METABOLISM IN THE F344 RAT OF 4-(N-METHYL-N-NITROSAMINO)-1-(3-PYRIDYL)-1-BUTANONE, A TOBACCO-SPECIFIC CARCINOGEN1980
- CHEMICAL STUDIES ON TOBACCO-SMOKE .62. ASSESSMENT OF TOBACCO-SPECIFIC N-NITROSAMINES IN TOBACCO PRODUCTS1979