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N-Nitrosonornicotine
Names
IUPAC name 3-(1-Nitrosopyrrolidin-2-yl)pyridine
Identifiers
CAS Number
3D model (JSmol)
Abbreviations NNN
ChemSpider
ECHA InfoCard 100.230.123 Edit this at Wikidata
KEGG
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C9H11N3O/c13-11-12-6-2-4-9(12)8-3-1-5-10-7-8/h1,3,5,7,9H,2,4,6H2/t9-/m0/s1Key: XKABJYQDMJTNGQ-VIFPVBQESA-N
  • InChI=1/C9H11N3O/c13-11-12-6-2-4-9(12)8-3-1-5-10-7-8/h1,3,5,7,9H,2,4,6H2/t9-/m0/s1Key: XKABJYQDMJTNGQ-VIFPVBQEBO
SMILES
  • O=NN2CCC2c1cnccc1
Properties
Chemical formula C9H11N3O
Molar mass 177.203 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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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

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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