N-Nitrosonornicotine
2540370
215086867
2008-05-26T17:20:35Z
209.139.203.25
{{Chembox new
| ImageFile = N-nitrosonornicotine-2D-skeletal.svg
| ImageSize = 200px
| IUPACName = 3-(1-Nitrosopyrrolidin-2-yl)pyridine
| OtherNames =
| Section1 = {{Chembox Identifiers
| Abbreviations = NNN
| CASNo = 16543-55-8
| PubChem = 27919
| SMILES = O=NN1CCCC1c2cccnc2
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>9</sub>H<sub>11</sub>N<sub>3</sub>O
| MolarMass = 177.20 g/mol
| Appearance = oily yellow liquid
| Density =
| MeltingPtC = 47
| BoilingPtC = 154
| Solubility = }}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| Autoignition = }}
}}
'''''N''-Nitrosonornicotine''' ('''NNN''') is a [[nitrosamine]] found in [[tobacco]] that has been classified by the [[IARC]] as a [[List of IARC Group 1 carcinogens|Group 1 carcinogen]].<ref>[http://monographs.iarc.fr/ENG/Classification/crthgr01.php IARC Overall Evaluations of Carcinogenicity to Humans]</ref>
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]], [[cigarette]]s, and [[cigar]]s. It is present in smoke from cigars and cigarettes, in the [[saliva]] of people who chew [[betel|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 [[endogenous]]ly from [[nitrite]] in saliva and tobacco [[alkaloid]]s including [[nicotine]].
== References ==
{{Reflist}}
{{DEFAULTSORT:Nitrosonornicotine, N-}}
[[Category:Carcinogens]]
[[Category:Pyridines]]
[[Category:Nitroso compounds]]
[[Category:Pyrrolidines]]