Synthesis of 4‐ (methylnitrosamino)‐1‐ (3‐pyridyl)‐1‐butanone, 4‐ (carbethoxynitrosamino)‐1‐ (3‐pyridyl)‐1‐butanone, and N′ ‐nitrosonornicotine labelled with tritium in the pyridine ring

James C. Wiley; David H.T. Chien; Nancy A. Nungesser; Dorothy Lin; Stephen S. Hecht

doi:10.1002/jlcr.2580250703

Synthesis of 4‐ (methylnitrosamino)‐1‐ (3‐pyridyl)‐1‐butanone, 4‐ (carbethoxynitrosamino)‐1‐ (3‐pyridyl)‐1‐butanone, and N′ ‐nitrosonornicotine labelled with tritium in the pyridine ring

James C. Wiley, David H.T. Chien, Nancy A. Nungesser, Dorothy Lin, Stephen S. Hecht

Laboratory Medicine and Pathology

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

Abstract

The carcinogenic tobacco‐specific nitrosamines 4‐(methylnitrosamino)‐1‐(3‐pyridyl)‐1‐butanone (NNK) and N′‐nitrosonornicotine (NNN), as well as the model compound 4‐(carbethoxynitrosamino)‐1‐(3‐pyridyl)‐1‐butanone, were synthesized with tritium at the 5‐position of the pyridine ring. In each case, the tritium labelled compound was prepared by catalytic tritium replacement of the corresponding brominated precursor.

Original language	English (US)
Pages (from-to)	707-716
Number of pages	10
Journal	Journal of Labelled Compounds and Radiopharmaceuticals
Volume	25
Issue number	7
DOIs	https://doi.org/10.1002/jlcr.2580250703
State	Published - Jul 1988

Keywords

NNK
NNN
Tritium labeled tobacco‐specific nitrosamines

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Wiley, J. C., Chien, D. H. T., Nungesser, N. A., Lin, D., & Hecht, S. S. (1988). Synthesis of 4‐ (methylnitrosamino)‐1‐ (3‐pyridyl)‐1‐butanone, 4‐ (carbethoxynitrosamino)‐1‐ (3‐pyridyl)‐1‐butanone, and N′ ‐nitrosonornicotine labelled with tritium in the pyridine ring. Journal of Labelled Compounds and Radiopharmaceuticals, 25(7), 707-716. https://doi.org/10.1002/jlcr.2580250703

Synthesis of 4‐ (methylnitrosamino)‐1‐ (3‐pyridyl)‐1‐butanone, 4‐ (carbethoxynitrosamino)‐1‐ (3‐pyridyl)‐1‐butanone, and N′ ‐nitrosonornicotine labelled with tritium in the pyridine ring. / Wiley, James C.; Chien, David H.T.; Nungesser, Nancy A.; Lin, Dorothy; Hecht, Stephen S.

In: Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 25, No. 7, 07.1988, p. 707-716.

Research output: Contribution to journal › Article › peer-review

Wiley, JC, Chien, DHT, Nungesser, NA, Lin, D & Hecht, SS 1988, 'Synthesis of 4‐ (methylnitrosamino)‐1‐ (3‐pyridyl)‐1‐butanone, 4‐ (carbethoxynitrosamino)‐1‐ (3‐pyridyl)‐1‐butanone, and N′ ‐nitrosonornicotine labelled with tritium in the pyridine ring', Journal of Labelled Compounds and Radiopharmaceuticals, vol. 25, no. 7, pp. 707-716. https://doi.org/10.1002/jlcr.2580250703

Wiley JC, Chien DHT, Nungesser NA, Lin D, Hecht SS. Synthesis of 4‐ (methylnitrosamino)‐1‐ (3‐pyridyl)‐1‐butanone, 4‐ (carbethoxynitrosamino)‐1‐ (3‐pyridyl)‐1‐butanone, and N′ ‐nitrosonornicotine labelled with tritium in the pyridine ring. Journal of Labelled Compounds and Radiopharmaceuticals. 1988 Jul;25(7):707-716. https://doi.org/10.1002/jlcr.2580250703

Wiley, James C. ; Chien, David H.T. ; Nungesser, Nancy A. ; Lin, Dorothy ; Hecht, Stephen S. / Synthesis of 4‐ (methylnitrosamino)‐1‐ (3‐pyridyl)‐1‐butanone, 4‐ (carbethoxynitrosamino)‐1‐ (3‐pyridyl)‐1‐butanone, and N′ ‐nitrosonornicotine labelled with tritium in the pyridine ring. In: Journal of Labelled Compounds and Radiopharmaceuticals. 1988 ; Vol. 25, No. 7. pp. 707-716.

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abstract = "The carcinogenic tobacco‐specific nitrosamines 4‐(methylnitrosamino)‐1‐(3‐pyridyl)‐1‐butanone (NNK) and N′‐nitrosonornicotine (NNN), as well as the model compound 4‐(carbethoxynitrosamino)‐1‐(3‐pyridyl)‐1‐butanone, were synthesized with tritium at the 5‐position of the pyridine ring. In each case, the tritium labelled compound was prepared by catalytic tritium replacement of the corresponding brominated precursor.",

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AB - The carcinogenic tobacco‐specific nitrosamines 4‐(methylnitrosamino)‐1‐(3‐pyridyl)‐1‐butanone (NNK) and N′‐nitrosonornicotine (NNN), as well as the model compound 4‐(carbethoxynitrosamino)‐1‐(3‐pyridyl)‐1‐butanone, were synthesized with tritium at the 5‐position of the pyridine ring. In each case, the tritium labelled compound was prepared by catalytic tritium replacement of the corresponding brominated precursor.

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