N-Nitrosonornicotine

N-Nitrosonornicotine
IUPAC name 3-(1-Nitrosopyrrolidin-2-yl)pyridine
Identifiers
Abbreviations	NNN
CAS number	16543-55-8
PubChem	27919
ChemSpider	19957766 Y
KEGG	C16452 Y
Jmol-3D images	Image 1
SMILES O=NN2CCC[C@H]2c1cnccc1
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/s1 Y Key: XKABJYQDMJTNGQ-VIFPVBQESA-N Y 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/s1 Key: XKABJYQDMJTNGQ-VIFPVBQEBO
Properties
Molecular formula	C9H11N3O
Molar mass	177.203 g/mol
Appearance	oily yellow liquid
Melting point	47 °C, 320 K, 117 °F
Boiling point	154 °C, 427 K, 309 °F
Solubility in water	soluble
Hazards
Flash point	177 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox 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