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.

Original languageEnglish (US)
Pages (from-to)226-230
Number of pages5
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Issue number5
StatePublished - Apr 2008

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Radiology Nuclear Medicine and imaging
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry


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