N-nitrosonornicotine (NNN) is a tobacco-specific nitrosamine that has been found to be carcinogenic in nature. This compound is produced through the nitrosation of nicotine during the curing, aging, processing and consumption of tobacco. N-nitrosonornicotine is abundant in all tobacco products, cigarette smoke, and even atmospheric particulate matter, as are the other tobacco-specific nitrosamines n-nitrosoanatabine and n-nitrosoanabazine. The toxication pathways of the metabolism of these compounds are important triggers for their carcinogenicity.
-analizi.jpg "NNN (N-Nitrosonornicotine) Analysis")
N-nitrosonornicotine is used as an analytical reference standard for the quantification of the analyte in biological samples using liquid chromatography combined with tandem mass spectrometry.
Tobacco-specific levels of n-nitrosonornicotine in tobacco are highly variable and significantly correlated with nitrate content in tobacco. This compound is classified as a carcinogen. Although not enough studies have been reported on the relationship between exposure to N-nitrosonornicotine and human cancer, there is sufficient evidence that this compound causes cancer in experimental animals.
Various tobacco products, including smokeless tobacco such as chewing tobacco and snuff, cigarettes and cigars, contain n-nitrosonornicotine. N-nitrosonornicotine has been found in cigar and cigarette smoke, in the saliva of tobacco chewers, and in the saliva of oral snuff and e-cigarette users.
A significant portion of the N-nitrosonornicotine originates from half unburned tobacco, with the remainder formed during combustion. Also, this compound is a nicotine derivative produced in acidic conditions in the stomach. N-nitrosonornicotine is formed in the stomach when stomach acid reacts with nitrite ions, which are typically used as salts to preserve red meats and inhibit bacterial growth.
The symptoms of N-nitrosonornicotine are very similar to nicotine poisoning. It can cause sleep disturbances, nausea and vomiting, chest pain, and headaches. Exposure to this compound is thought to cause cancer ; it has been proven to cause esophageal and nasal cancer in animals. Therefore, there is no known safe level for this compound.
The level of n-nitrosonornicotine detected in cigarette smoke is between 2.2-6.6 parts per million (ppm). The US Food and Drug Administration (FDA) has set limits for nitrosamines in cured meats, for example, to less than 10 parts per billion (ppb).
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