N-Nitrosonornicotine
- CAS No.
- 53759-22-1
- Chemical Name:
- N-Nitrosonornicotine
- Synonyms
- 3-(1-Nitrosopyrrolidin-2-yl)pyridine
- CBNumber:
- CB91485311
- Molecular Formula:
- C9H11N3O
- Molecular Weight:
- 0
- MDL Number:
- MOL File:
- Mol file
N-Nitrosonornicotine Chemical Properties,Uses,Production
Chemical Properties
Nitrosonornicotine is prepared by reacting nornicotine with nitrous acid or by reacting nicotine with excess nitrite at approximately pH 4. It is a yellowoil. NNN is somewhat soluble in water and very soluble in slightly acidified water and in organic solvents. Like other nitrosamines, it can be oxidized and reduced and has additional reactions due to the pyridine ring, such as formation of the N-oxide.
Production Methods
There is no evidence that NNN has been manufactured commercially but it is used as a research chemical. NNN belongs in the category of so-called tobacco-specific nitrosamines because it has been found only associated with tobacco or with tobacco smoking. There is substantial exposure to NNN of humans who smoke tobacco or use snuff or chewing tobacco. NNN was not present in freshly harvested tobacco but was present in snuff (12–29 mg/kg), in cigars (up to 11 mg/kg), in chewing tobacco (as much as 90 mg/kg), and in other tobacco products. NNN can be formed in the mouth by interaction of nicotine eluted from the tobacco with nitrite in the saliva; the nicotine may also be swallowed and react with nitrite in the stomach. NNN has also been identified in tobacco smoke (140 ng per cigarette up to 10 times that). An extensive survey of the amount of nitrosamines, including NNN, in the mainstream and in the sidestream smoke of cigarettes and cigars showed large variations from 0.1 μg/cigarette to 3.7 μg and more in cigar smoke. Evidence from one comparative study of tobacco-specific nitrosamines in cigarettes suggests that levels of NNN (measured as a sum of all tobacco-specific nitrosamines) are higher in non-Moldovan cigarette tobacco and Moldovan blended cigarettes, suggesting that current tobacco production and manufacturing technologies may create conditions that favor N-nitrosation of alkaloids and other tobacco constituents.
Definition
ChEBI: N'-Nitrosonornicotine is a member of pyrrolidines and a member of pyridines.
Carcinogenicity
NNN is classified as reasonably anticipated to be a human carcinogen by NTP and carcinogenic to humans (Group 1) by IARC. In several strains of rat, oral administration of NNN induced tumors of the esophagus and nasal cavity or nasal cavity tumors only (drinking water treatment). In mice by i.p. injection, there were lung tumors, and in hamsters subcutaneous injection led to tumors of the trachea and nasal cavity, while similar exposures via subcutaneous injection induced nasal cavity tumors in rats.