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 |
|---|---|---|
| Carcinogenicity of N'-nitrosonornicotine in Sprague-Dawley rats. | 1976 Dec |
|
| Comparative carcinogenicity in F344 rats of the tobacco-specific nitrosamines, N'-nitrosonornicotine and 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone. | 1980 Feb |
|
| 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 Feb |
|
| 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 |
|
| Role of human cytochrome P450 (CYP) in the metabolic activation of nitrosamine derivatives: application of genetically engineered Salmonella expressing human CYP. | 2002 Aug |
|
| Nicotinic receptors mediate tumorigenic action of tobacco-derived nitrosamines on immortalized oral epithelial cells. | 2006 May |
|
| The nicotinic receptor antagonists abolish pathobiologic effects of tobacco-derived nitrosamines on BEP2D cells. | 2006 Oct |
|
| Functional characterization of CYP2A13 polymorphisms. | 2007 Dec |
|
| A susceptibility locus for lung cancer maps to nicotinic acetylcholine receptor subunit genes on 15q25. | 2008 Apr 3 |
|
| Mouse model of diethylnitrosamine-induced gastric cancer. | 2008 Aug |
|
| Glucuronidation of tobacco-specific nitrosamines by UGT2B10. | 2008 May |
|
| CYP2A6 polymorphisms and risk for tobacco-related cancers. | 2008 Nov |
|
| In vitro exposure of tobacco specific nitrosamines decreases the rat lung phospholipids by enhanced phospholipase A2 activity. | 2014 Sep |
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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admin
on
Edited
Fri Dec 15 21:16:07 UTC 2023
by
admin
on
Fri Dec 15 21:16:07 UTC 2023
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| Record UNII |
X656TZ86DX
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| Record Status |
Validated (UNII)
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| Record Version |
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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 | ||
|---|---|---|---|---|
|
METABOLITE -> PARENT |
Pre-clinical;
IN-VIVO
URINE
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