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
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24830349 |
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Target ID: CHEMBL1907589 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26441658 |
1.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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Carcinogenicity of N'-nitrosonornicotine in Sprague-Dawley rats. | 1976 Dec |
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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 |
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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 |
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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 |
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Role of human cytochrome P450 (CYP) in the metabolic activation of nitrosamine derivatives: application of genetically engineered Salmonella expressing human CYP. | 2002 Aug |
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Nicotinic receptors mediate tumorigenic action of tobacco-derived nitrosamines on immortalized oral epithelial cells. | 2006 May |
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The nicotinic receptor antagonists abolish pathobiologic effects of tobacco-derived nitrosamines on BEP2D cells. | 2006 Oct |
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Glucuronidation of tobacco-specific nitrosamines by UGT2B10. | 2008 May |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8469543
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.
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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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METABOLITE (PARENT)
SUBSTANCE RECORD