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Details

Stereochemistry EPIMERIC
Molecular Formula C10H14N2O
Molecular Weight 178.231
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NICOTINE N'-OXIDE

SMILES

C[N+]1([O-])CCC[C@H]1C2=CC=CN=C2

InChI

InChIKey=RWFBQHICRCUQJJ-NUHJPDEHSA-N
InChI=1S/C10H14N2O/c1-12(13)7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3/t10-,12?/m0/s1

HIDE SMILES / InChI

Molecular Formula C10H14N2O
Molecular Weight 178.231
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 1 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Nicotine-1'-N-oxide (NNO) is an oxidation product of nicotine. Flavin-containing monooxygenase is responsible for the oxygen transfer. Nicotine N'- oxide is a primary metabolite of nicotine, although only about 4-7% of nicotine absorbed by smokers is metabolized via this route. It appears that NNO is not further metabolized to any significant extent, except by reduction back to nicotine, which may lead to recycling of nicotine in the body.

Originator

Curator's Comment: N-oxides of S-(-)-nicotine have been synthesized and characterized by Phillipson and Handa

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Cigarette smoking inhibits prostacyclin formation.
1983 Jun 4
Evaluation of the effects of cotinine and nicotine-N'-oxides on the development of tumors in rats initiated with N-[4-(5-nitro-2-furyl)-2-thiazolyl]formamide.
1985 Dec
Simultaneous determination of nicotine and cotinine in various human tissues using capillary gas chromatography/mass spectrometry.
1994
Inhaled nicotine in humans: effect on the respiratory and cardiovascular systems.
1994 Jun
The effect of nicotine on in vitro sperm motion characteristics.
1995 Mar
The maternal and fetal physiologic effects of nicotine.
1996 Apr
No acute effects of smoking and nicotine nasal spray on lipolysis measured by subcutaneous microdialysis.
1997 Jun
Plasma nitric oxide before and after smoking cessation with nicotine nasal spray.
1998 Jan
[The Tuaregs addiction to tea, to smokeless tobacco and to milk: ethnological and clinical approach].
2003 Jan-Feb
Determination of arecoline (areca nut alkaloid) and nicotine in hair by high-performance liquid chromatography/electrospray quadrupole mass spectrometry.
2005
Cotinine, a neuroactive metabolite of nicotine: potential for treating disorders of impaired cognition.
2005 Autumn
Attenuation of Abeta deposition in the entorhinal cortex of normal elderly individuals associated with tobacco smoking.
2005 Oct
Regional and cellular distribution of CYP2E1 in monkey brain and its induction by chronic nicotine.
2006 Apr
Current status of immunologic approaches to treating tobacco dependence: vaccines and nicotine-specific antibodies.
2006 Feb 24
Nicotine metabolite ratio predicts efficacy of transdermal nicotine for smoking cessation.
2006 Jun
[Development of analytical method for determination nicotine metabolites in urine].
2009
UGT2B10 genotype influences nicotine glucuronidation, oxidation, and consumption.
2010 Jun
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Other
Nicotine-1'-N-oxide (1-10 μM) weakly inhibited human platelets adhesion to fibrinogen
Substance Class Chemical
Created
by admin
on Wed Apr 02 12:27:06 GMT 2025
Edited
by admin
on Wed Apr 02 12:27:06 GMT 2025
Record UNII
9R173T257I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NICOTINE N'-OXIDE
Systematic Name English
(-)-NICOTINE 1'-OXIDE
Preferred Name English
NICOTINE RELATED COMPOUND E [USP IMPURITY]
Common Name English
N-OXYNICOTINE
Common Name English
S-(-)-NICOTINE-1'-N-OXIDE
Common Name English
NICOTINE 1'-N-OXIDE
Common Name English
(1RS,2S)-1-METHYL-2-(PYRIDIN-3-YL)PYRROLIDINE 1-OXIDE
Systematic Name English
PYRIDINE, 3-((2S)-1-METHYL-1-OXIDO-2-PYRROLIDINYL)-
Systematic Name English
NICOTINE, 1'-OXIDE
Common Name English
NICOTINE RESINATE IMPURITY E [EP IMPURITY]
Common Name English
NICOTINE DITARTRATE DIHYDRATE IMPURITY E [EP IMPURITY]
Common Name English
NICOTINE IMPURITY E [EP IMPURITY]
Common Name English
S-NICOTINE-N-OXIDE
Common Name English
Code System Code Type Description
CHEBI
142659
Created by admin on Wed Apr 02 12:27:06 GMT 2025 , Edited by admin on Wed Apr 02 12:27:06 GMT 2025
PRIMARY
EPA CompTox
DTXSID70867021
Created by admin on Wed Apr 02 12:27:06 GMT 2025 , Edited by admin on Wed Apr 02 12:27:06 GMT 2025
PRIMARY
CAS
491-26-9
Created by admin on Wed Apr 02 12:27:06 GMT 2025 , Edited by admin on Wed Apr 02 12:27:06 GMT 2025
PRIMARY
PUBCHEM
68107
Created by admin on Wed Apr 02 12:27:06 GMT 2025 , Edited by admin on Wed Apr 02 12:27:06 GMT 2025
PRIMARY
FDA UNII
9R173T257I
Created by admin on Wed Apr 02 12:27:06 GMT 2025 , Edited by admin on Wed Apr 02 12:27:06 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
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USP
PARENT -> IMPURITY