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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
Structure of N-NITROSONORNICOTINE

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

HIDE SMILES / InChI
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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2311221
1.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
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
Glucuronidation of tobacco-specific nitrosamines by UGT2B10.
2008 May
Patents

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
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.
Name Type Language
N-NITROSONORNICOTINE
HSDB  
Common Name English
ANTI-N'-NITROSONORNICOTINE
Common Name English
NNN
Common Name English
NICOTINE, 1'-DEMETHYL-1'-NITROSO-
Common Name English
PYRIDINE, 3-(1-NITROSO-2-PYRROLIDINYL)-, (S)-
Common Name English
N'-NITROSONORNICOTINE [IARC]
Common Name English
N'-NITROSONORNICOTINE
Common Name English
SYN-N'-NITROSONORNICOTINE
Common Name English
N-NITROSONORNICOTINE [HSDB]
Common Name English
PYRIDINE, 3-((2S)-1-NITROSO-2-PYRROLIDINYL)-
Systematic Name English
Code System Code Type Description
HSDB
5114
Created by admin on Fri Dec 15 21:16:07 GMT 2023 , Edited by admin on Fri Dec 15 21:16:07 GMT 2023
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MESH
C008655
Created by admin on Fri Dec 15 21:16:07 GMT 2023 , Edited by admin on Fri Dec 15 21:16:07 GMT 2023
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PUBCHEM
12613538
Created by admin on Fri Dec 15 21:16:07 GMT 2023 , Edited by admin on Fri Dec 15 21:16:07 GMT 2023
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EPA CompTox
DTXSID4021476
Created by admin on Fri Dec 15 21:16:07 GMT 2023 , Edited by admin on Fri Dec 15 21:16:07 GMT 2023
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CAS
16543-55-8
Created by admin on Fri Dec 15 21:16:07 GMT 2023 , Edited by admin on Fri Dec 15 21:16:07 GMT 2023
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WIKIPEDIA
N-NITROSONORNICOTINE
Created by admin on Fri Dec 15 21:16:07 GMT 2023 , Edited by admin on Fri Dec 15 21:16:07 GMT 2023
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NCI_THESAURUS
C44414
Created by admin on Fri Dec 15 21:16:07 GMT 2023 , Edited by admin on Fri Dec 15 21:16:07 GMT 2023
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FDA UNII
X656TZ86DX
Created by admin on Fri Dec 15 21:16:07 GMT 2023 , Edited by admin on Fri Dec 15 21:16:07 GMT 2023
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