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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

[H][C@]1(CCC[N+]1(C)[O-])C2=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
The effect of nicotine on in vitro sperm motion characteristics.
1995 Mar
The maternal and fetal physiologic effects of nicotine.
1996 Apr
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 Sat Dec 16 18:51:42 UTC 2023
Edited
by admin
on Sat Dec 16 18:51:42 UTC 2023
Record UNII
9R173T257I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NICOTINE N'-OXIDE
Systematic 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
(-)-NICOTINE 1'-OXIDE
Common 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 Sat Dec 16 18:51:42 UTC 2023 , Edited by admin on Sat Dec 16 18:51:42 UTC 2023
PRIMARY
EPA CompTox
DTXSID70867021
Created by admin on Sat Dec 16 18:51:42 UTC 2023 , Edited by admin on Sat Dec 16 18:51:42 UTC 2023
PRIMARY
CAS
491-26-9
Created by admin on Sat Dec 16 18:51:42 UTC 2023 , Edited by admin on Sat Dec 16 18:51:42 UTC 2023
PRIMARY
PUBCHEM
68107
Created by admin on Sat Dec 16 18:51:42 UTC 2023 , Edited by admin on Sat Dec 16 18:51:42 UTC 2023
PRIMARY
FDA UNII
9R173T257I
Created by admin on Sat Dec 16 18:51:42 UTC 2023 , Edited by admin on Sat Dec 16 18:51:42 UTC 2023
PRIMARY
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PARENT -> IMPURITY
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EP