- Syntheses of isotope-labeled tobacco-specific nitrosamines and their metabolites
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We report here on the syntheses of three deuterium-labeled tobacco-specific nitrosamines namely [2,4,5,6-d4]nitroso-nornicotine([2,4,5,6-d 4]NNN), 4-(methylnitrosamino)-1-(3-[2,4,5,6-d4]pyridyl)-1- butanone ([2,4,5,6-d4]NNK), and 4-(methyl-nitrosamino)-1-(3-[2,4,5,6- d4]pyridyl)-1-butanol ([2,4,5,6-d4]NNAL). A metabolite of NNK and myosmine, 4-hydroxy-1-(3-[2,4,5,6-d4]pyridyl)-1-butanone, was also synthesized. The synthetic strategy reported here is similar to that reported in the literature for the preparation of corresponding unlabeled compounds. The commercially available [2,4,5,6-d4]ethylnicotinate was used as starting material. During the course of these syntheses [2,4,5,6-d 4]myosmme and [2,4,5,6-d4]nornicotine were obtained as stable intermediates. These isotope-labeled compounds are useful internal standards for quantification of TSNA and their metabolites in smokers in molecular epidemiological studies. Copyright
- Desai, Dhimant,Krzeminski, Jacek,El-Bayoumy, Karam,Amin, Shantu
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p. 226 - 230
(2008/12/20)
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- Synthesis of partially deuterated N-nitrosamines - New standards in tobacco-smoke analysis
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N-Nitrosamines of tobacco alkaloids contribute to the cause of tobacco related cancers and, therefore, they are important analytes. Herein the preparation of four partially deuterated N-nitrosamines from simple, commercially available, deuterated educts is described, which can serve as useful standards in tobacco-smoke analysis. Springer-Verlag 2004.
- Gaertner, Peter,Bica, Katharina,Einzinger, Christian
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p. 549 - 555
(2007/10/03)
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