4-(N-NITROSOMETHYLAMINO)-1-(3-PYRIDYL)-1-BUTANONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H13N3O2
Molecular Weight	207.2291
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

Structure Search

SMILES

CN(CCCC(=O)C1=CN=CC=C1)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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24830349

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

Primary Target	Pharmacology	Condition	Potency
Neuronal acetylcholine receptor; alpha4/beta2 77 Target ID: CHEMBL1907589 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26441658	Partial Agonist 297		16.7 µM [EC50]
DNA 282 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24830349	Binding Agent 1076

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Mechanisms of Cancer Induction by Tobacco-Specific NNK and NNN.	2014-05-14	24830349
Bcl2 Family Functions as Signaling Target in Nicotine-/NNK-Induced Survival of Human Lung Cancer Cells.	2014	24967145

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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.

Name

Type

Language

4-(METHYLNITROSAMINO)-1-(3-PYRIDYL)-1-BUTANONE

Preferred Name

English

4-(N-NITROSOMETHYLAMINO)-1-(3-PYRIDYL)-1-BUTANONE

Systematic Name

English

4-(N-NITROSOMETHYLAMINO)-1-(3-PYRIDYL)-1-BUTANONE [IARC]

Common Name

English