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| Names | |
|---|---|
| IUPAC name 3-(1-Nitrosopyrrolidin-2-yl)pyridine | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| Abbreviations | NNN |
| ChemSpider | |
| ECHA InfoCard | 100.230.123 
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| KEGG | |
| PubChem CID | |
| CompTox Dashboard (EPA) | |
InChI
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SMILES
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| Properties | |
| Chemical formula | C9H11N3O |
| Molar mass | 177.207 g·mol |
| Appearance | Oily yellow liquid |
| Melting point | 47 °C (117 °F; 320 K) |
| Boiling point | 154 °C (309 °F; 427 K) |
| Solubility in water | Soluble |
| Hazards | |
| Flash point | 177 °C (351 °F) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 Y verify (what is ?)
Infobox references
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N-Nitrosonornicotine (NNN) is a nitrosamine found in tobacco that has been classified by the IARC as a Group 1 carcinogen. NNN is produced from nornicotine during the curing and processing of tobacco.
Although no adequate studies of the relationship between exposure to NNN and human cancer have been reported, there is sufficient evidence that NNN causes cancer in experimental animals.
NNN is found in a variety of tobacco products including chewing tobacco, snuff, cigarettes, and cigars. It is present in smoke from cigars and cigarettes, in the saliva of people who chew betel quid with tobacco, and in the saliva of oral-snuff users. NNN is produced by the nitrosation of nicotine during the curing, ageing, processing, and smoking of tobacco. Roughly half of the NNN originates in the unburnt tobacco, with the remainder being formed during burning.
Some of the NNN present in the saliva of tobacco users is produced endogenously from nitrite in saliva and tobacco alkaloids including nicotine.
References
- IARC Overall Evaluations of Carcinogenicity to Humans
- Siminszky, B. (2005). "Conversion of nicotine to nornicotine in Nicotiana tabacum is mediated by CYP82E4, a cytochrome P450 monooxygenase". Proceedings of the National Academy of Sciences. 102 (41): 14919. doi:10.1073/pnas.0506581102.