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Details

Stereochemistry ACHIRAL
Molecular Formula C10H13N3O2
Molecular Weight 207.2295
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-(N-NITROSOMETHYLAMINO)-1-(3-PYRIDYL)-1-BUTANONE

SMILES

CN(CCCC(=O)c1cccnc1)N=O

InChI

InChIKey=FLAQQSHRLBFIEZ-UHFFFAOYSA-N
InChI=1S/C10H13N3O2/c1-13(12-15)7-3-5-10(14)9-4-2-6-11-8-9/h2,4,6,8H,3,5,7H2,1H3

HIDE SMILES / InChI

Molecular Formula C10H13N3O2
Molecular Weight 207.2295
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone or nicotine-derived nitrosamine ketone (NNK) is a tobacco-specific nitrosamine. NNK is considered to be a carcinogen. NNK induces deleterious mutations in oncogenes and tumor suppression genes by forming DNA adducts, which could be considered as tumor initiation. Meanwhile, the binding of NNK 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
16.6999999999999993 µM [EC50]
Target ID: CHEMBL2311221
PubMed

PubMed

TitleDatePubMed
Bcl2 Family Functions as Signaling Target in Nicotine-/NNK-Induced Survival of Human Lung Cancer Cells.
2014
Mechanisms of Cancer Induction by Tobacco-Specific NNK and NNN.
2014 May 14
Patents

Sample Use Guides

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) 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
V79 cells were induced with different concentrations of 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) (0.1-0.4 mg/mL), and the expression levels of six Prx genes (Prx1-Prx6) were measured by qRT-PCR 24 h following NNK treatment.
Substance Class Chemical
Created
by admin
on Sat Jun 26 13:27:41 UTC 2021
Edited
by admin
on Sat Jun 26 13:27:41 UTC 2021
Record UNII
7S395EDO61
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
4-(N-NITROSOMETHYLAMINO)-1-(3-PYRIDYL)-1-BUTANONE
Systematic Name English
4-(METHYLNITROSAMINO)-1-(3-PYRIDYL)-1-BUTANONE
Common Name English
4-(N-NITROSOMETHYLAMINO)-1-(3-PYRIDYL)-1-BUTANONE [IARC]
Common Name English
METHYLNITROSOAMINO-1-(3-PYRIDINYL)-1-BUTANONE, 4-
Systematic Name English
4-(N-METHYL-N-NITROSAMINO)-1-(3-PYRIDYL)-1-BUTANONE
Common Name English
NNK
Common Name English
1-BUTANONE, 4-(METHYLNITROSOAMINO)-1-(3-PYRIDINYL)-
Systematic Name English
NNK (CARCINOGEN) [HSDB]
Common Name English
4-(N-NITROSOMETHYLAMINO)-1-(3-PYRIDINYL)-1-BUTANONE
Systematic Name English
Code System Code Type Description
CAS
64091-91-4
Created by admin on Sat Jun 26 13:27:41 UTC 2021 , Edited by admin on Sat Jun 26 13:27:41 UTC 2021
PRIMARY
PUBCHEM
47289
Created by admin on Sat Jun 26 13:27:41 UTC 2021 , Edited by admin on Sat Jun 26 13:27:41 UTC 2021
PRIMARY
HSDB
7771
Created by admin on Sat Jun 26 13:27:41 UTC 2021 , Edited by admin on Sat Jun 26 13:27:41 UTC 2021
PRIMARY
EPA CompTox
64091-91-4
Created by admin on Sat Jun 26 13:27:41 UTC 2021 , Edited by admin on Sat Jun 26 13:27:41 UTC 2021
PRIMARY
FDA UNII
7S395EDO61
Created by admin on Sat Jun 26 13:27:41 UTC 2021 , Edited by admin on Sat Jun 26 13:27:41 UTC 2021
PRIMARY
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Highly effective lung carcinogen in rats and induces lung tumors in mice and hamsters as well (1) . It also causes tumors of the pancreas, liver, and nasal mucosa in rats. NNK (ng/cigarette)Canadian = 448.5 SD(237.4)Imported = 437.2 SD(376.1)
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