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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

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

Targets

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
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
Role of human cytochrome P450 (CYP) in the metabolic activation of nitrosamine derivatives: application of genetically engineered Salmonella expressing human CYP.
2002 Aug
The nicotinic receptor antagonists abolish pathobiologic effects of tobacco-derived nitrosamines on BEP2D cells.
2006 Oct
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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 21:16:07 GMT 2023
Edited
by admin
on Fri Dec 15 21:16:07 GMT 2023
Record UNII
X656TZ86DX
Record Status Validated (UNII)
Record Version
  • Download
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
NNN (ng/cigarette) Canadian = 286.9 SD(118.3) Imported = 1776.2 SD(817.2)
PARENT -> DERIVATIVE
Carcinogenic substance present in cigarette smoke
Related Record Type Details
METABOLITE -> PARENT
Pre-clinical;
IN-VIVO
URINE