NNK

Nicotine-derived nitrosamine ketone (NNK) is one of the key tobacco-specific nitrosamines (TSNAs) derived from nicotine. It plays an important role in carcinogenesis. The conversion of nicotine to NNK entails opening of the pyrrolidine ring.

Nicotine-derived nitrosamine ketone (NNK) is one of the key tobacco-specific nitrosamines (TSNAs) derived from nicotine. It plays an important role in carcinogenesis. The conversion of nicotine to NNK entails opening of the pyrrolidine ring.

Synthesis and occurrence

NNK can be produced by standard methods of organic synthesis.

Tobacco

NNK is both found in cured tobacco and produced during its burning (pyrolysis). The amount delivered in cigarette smoke ranged from 30 to 280 ng per cigarette in one study and 12 to 110 ng per cigarette in another. Sun-cured ("Oriental") tobaccos contain very little NNK and other TSNAs due to being grown in low-nitrate soil, lack of nitrate fertilizer, and sun-curing. Flue-cured tobacco ("Virginia" tobacco ), especially when cured using an open flame, contains most of the NNK in American blended tobaccos, although Marlboro's "Virginia blend" had the lowest levels of NNK per nicotine out of many tested, with the exception of Natural American Spirit.

e-Cigarettes

e-Cigarettes do not convert nicotine to NNK due to their lower operating temperatures. The amount of NNK delivered by e-cigarettes reaches 2.8 ng per 15 puffs (approximately 1 cigarette). NNK was found in 89% of Korean e-cigarette liquids. Concentrations range from 0.22 to 9.84 μg/L. For the product that had the highest amount, if 1 ml is equivalent to 20 cigarettes, there would be 9.84/20 = 0.5 ng NNK per e-cig cigarette dose. Cigarettes with 1 gram of tobacco average about 350 ng.

Text derived from https://en.wikipedia.org/w/index.php?oldid=1375607969 under CC BY-SA 4.0; modifications have been made.