N-Nitrosonornicotine

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N-Nitrosonornicotine
N-nitrosonornicotine-2D-skeletal.svg
Identifiers
Abbreviations NNN
CAS number 16543-55-8 YesY
PubChem 27919
ChemSpider 19957766 YesY
KEGG C16452 YesY
Jmol-3D images Image 1
Properties
Molecular formula C9H11N3O
Molar mass 177.20 g mol−1
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; 450 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

N-Nitrosonornicotine (NNN) is a nitrosamine produced during the curing and processing of tobacco and 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 smokeless tobacco like chewing tobacco and snuff,[2] 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 nornicotine during the curing, aging, processing, and smoking of tobacco.[3] Roughly half of the NNN originates in the unburnt tobacco, with the remainder being formed during burning.

NNN can be produced in the acidic environment of the stomach in users of oral nicotine replacement therapies, due to the combination of dietary/endogenous nitrates, and nornicotine(either present as a minor metabolite of nicotine, or as an impurity in the product). Levels found in urine are over an order of magnitude less than when tobacco is consumed, but this remains a potential source of cancer when used in the long term.[4]

References[edit]

  1. ^ "Agents Classified by the IARC Monographs, Volumes 1–105". IARC. 
  2. ^ Balbo, S. (April 2, 2012). "Strong Oral Carcinogen Identified in Smokeless Tobacco". American Association for Cancer Research. 
  3. ^ Siminszky, B.; Gavilano, L.; Bowen, S. W.; Dewey, R. E. (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): 14919–14924. doi:10.1073/pnas.0506581102. PMC 1253577. PMID 16192354. 
  4. ^ http://www.fda.gov/downloads/Drugs/NewsEvents/UCM232146.pdf