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N-Nitrosonornicotine

N-Nitrosonornicotine
IUPAC name 3-(1-Nitrosopyrrolidin-2-yl)pyridine
Identifiers
Abbreviations NNN
CAS number [16543-55-8]
PubChem 27919
SMILES O=NN1CCCC1c2cccnc2
Properties
Molecular formula C9H11N3O
Molar mass 177.20 g/mol
Appearance oily yellow liquid
Melting point

47 °C, 320 K, 117 °F
Boiling point

154 °C, 427 K, 309 °F
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

N-Nitrosonornicotine (NNN) is a nitrosamine found in tobacco that has been classified by the IARC as a Group 1 carcinogen.[1]

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

  1. ^ IARC Overall Evaluations of Carcinogenicity to Humans
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