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Syntheses of isotope‐labeled tobacco‐specific nitrosamines and their metabolites
Author(s) -
Desai Dhimant,
Krzeminski Jacek,
ElBayoumy Karam,
Amin Shantu
Publication year - 2008
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.1508
Subject(s) - chemistry , nornicotine , metabolite , nitrosamine , carcinogen , stereochemistry , chromatography , organic chemistry , alkaloid , biochemistry
We report here on the syntheses of three deuterium‐labeled tobacco‐specific nitrosamines namely [2,4,5,6‐d 4 ]nitrosonornicotine([2,4,5,6‐d 4 ]NNN), 4‐(methylnitrosamino)‐1‐(3‐[2,4,5,6‐d 4 ]pyridyl)‐1‐butanone ([2,4,5,6‐d 4 ]NNK), and 4‐(methylnitrosamino)‐1‐(3‐[2,4,5,6‐d 4 ]pyridyl)‐1‐butanol ([2,4,5,6‐d 4 ]NNAL). A metabolite of NNK and myosmine, 4‐hydroxy‐1‐(3‐[2,4,5,6‐d 4 ]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‐d 4 ]ethylnicotinate was used as starting material. During the course of these syntheses [2,4,5,6‐d 4 ]myosmine and [2,4,5,6‐d 4 ]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 © 2008 John Wiley & Sons, Ltd.