title: Effect of storage conditions on nitrosated, acylated, and oxidized pyridine alkaloid derivatives in smokeless tobacco products.
abstract: Very large concentration increases in nitrite (34-fold), nitrosated pyridine alkaloids, and related 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) (14- to 33-fold) occurred in moist snuff during storage at 24 degrees C for 52 weeks, whereas, decreases in all parent and some acylated pyridine alkaloids were observed in the same material. Nitrite concentrations in dry snuff decreased up to 90% during storage; increased contents of nitrosated alkaloids and NNK of 30 to 80% were also observed. Storage effects on chewing tobacco included a 75% increase in nitrite and small increases of nitrosated alkaloids and NNK. Sums of parent alkaloids in moist snuff decreased 24 and 54% after storage for 24 weeks at 24 and 32 degrees C, respectively, while sums of alkaloid derivatives increased, up to 36-fold for nitrosated alkaloids and NNK, 92% for acylated, and 133% for oxidized components. Levels of N'-nitrosonornicotine, NNK, and N'-nitrosoanatabine after 52 weeks' storage at 24 degrees C were 547, 41, and 296% higher, respectively, in ambient air-exposed moist snuff than in the nonexposed counterpart. A mathematical model was evaluated and used to calibrate nonlinear gas chromatography alkali bead detector response to the individual components. This permitted the use of a single analysis for all required individual compounds over a wide concentration range.
authors: Agricultural Research Service, University of Kentucky, Lexington 40546.
authors: R A
authors: RA
authors: Andersen
authors: H R
authors: HR
authors: Burton
authors: P D
authors: PD
authors: Fleming
authors: T R
authors: TR
authors: Hamilton-Kemp
mesh_terms: D000215:Acylation; D000470:Alkaloids / Q000032:analysis*; D004355:Drug Stability; D009573:Nitrites / Q000032:analysis; D009603:Nitroso Compounds / Q000032:analysis*; D010084:Oxidation-Reduction; D010947:Plants, Toxic; D011725:Pyridines / Q000032:analysis*; D012044:Regression Analysis; D014026:Nicotiana / Q000032:analysis*; D014030:Tobacco, Smokeless / Q000032:analysis*
chemical_list: D000470:Alkaloids; D009573:Nitrites; D009603:Nitroso Compounds; D011725:Pyridines