Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C9H11N3O |
| Molecular Weight | 177.2031 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O=NN1CCC[C@H]1C2=CN=CC=C2
InChI
InChIKey=XKABJYQDMJTNGQ-VIFPVBQESA-N
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
| Molecular Formula | C9H11N3O |
| Molecular Weight | 177.2031 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
N‑Nitrosonornicotine (NNN) is a nitrosamine compound. It is produced by nitrosation of nicotine during the curing, aging, processing, and smoking of tobacco. About half of the NNN originates in the unburnt tobacco, whereas the remainder is formed during burning. NNN is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals. NNN induces deleterious mutations in oncogenes and tumor suppression genes by forming DNA adducts, which could be considered as tumor initiation. Meanwhile, the binding of NNN to the nicotinic acetylcholine receptor promotes tumor growth by enhancing and deregulating cell proliferation, survival, migration, and invasion, thereby creating a microenvironment for tumor growth.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| In vitro exposure of tobacco specific nitrosamines decreases the rat lung phospholipids by enhanced phospholipase A2 activity. | 2014-09 |
|
| CYP2A6 polymorphisms and risk for tobacco-related cancers. | 2008-11 |
|
| Mouse model of diethylnitrosamine-induced gastric cancer. | 2008-08 |
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| Glucuronidation of tobacco-specific nitrosamines by UGT2B10. | 2008-05 |
|
| A susceptibility locus for lung cancer maps to nicotinic acetylcholine receptor subunit genes on 15q25. | 2008-04-03 |
|
| Functional characterization of CYP2A13 polymorphisms. | 2007-12 |
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| The nicotinic receptor antagonists abolish pathobiologic effects of tobacco-derived nitrosamines on BEP2D cells. | 2006-10 |
|
| Nicotinic receptors mediate tumorigenic action of tobacco-derived nitrosamines on immortalized oral epithelial cells. | 2006-05 |
|
| Role of human cytochrome P450 (CYP) in the metabolic activation of nitrosamine derivatives: application of genetically engineered Salmonella expressing human CYP. | 2002-08 |
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| Predicting the mutagenicity of tobacco-related N-nitrosamines in humans using 11 strains of Salmonella typhimurium YG7108, each coexpressing a form of human cytochrome P450 along with NADPH-cytochrome P450 reductase. | 2001 |
|
| Comparative metabolism of the tobacco-related carcinogens benzo[a]pyrene, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol, and N'- nitrosonornicotine in human hepatic microsomes. | 1997-02 |
|
| Comparative carcinogenicity in F344 rats of the tobacco-specific nitrosamines, N'-nitrosonornicotine and 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone. | 1980-02 |
|
| Carcinogenicity of N'-nitrosonornicotine in Sprague-Dawley rats. | 1976-12 |
Sample Use Guides
N‑Nitrosonornicotine has been tested for carcinogenicity by various routes of administration in adult mice, rats, and Syrian hamsters, and in limited experiments in mink and ferrets.
Route of Administration:
Other
Epithelial monolayers were subsequently subcultured and then treated for 1 hour with 0.25 to 1.0 ng/ml of N-nitrosonornicotine. Even though the controls and most treatment groups terminally differentiated, cells exposed to N-nitrosonornicotine continued to divide, maintained a differentiated phenotype for 8 1/2 to 10 weeks in culture, and displayed focal growth and morphologic changes suggestive of early stages in cell transformation.
| Substance Class |
Chemical
Created
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Mon Mar 31 20:17:22 GMT 2025
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on
Mon Mar 31 20:17:22 GMT 2025
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| Record UNII |
X656TZ86DX
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Validated (UNII)
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5114
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C008655
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12613538
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DTXSID4021476
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16543-55-8
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N-NITROSONORNICOTINE
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C44414
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X656TZ86DX
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> CONSTITUENT ALWAYS PRESENT |
NNN (ng/cigarette)
Canadian = 286.9 SD(118.3)
Imported = 1776.2 SD(817.2)
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PARENT -> DERIVATIVE |
Carcinogenic substance present in cigarette smoke
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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METABOLITE -> PARENT |
Pre-clinical;
IN-VIVO
URINE
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