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
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
| 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
Sources: https://books.google.at/books?id=VhrtCAAAQBAJ&printsec=frontcover&hl=ru#v=onepage&q&f=false
Curator's Comment: N-oxides of S-(-)-nicotine have been synthesized and characterized by Phillipson and Handa
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| UGT2B10 genotype influences nicotine glucuronidation, oxidation, and consumption. | 2010-06 |
|
| [Development of analytical method for determination nicotine metabolites in urine]. | 2009 |
|
| Nicotine metabolite ratio predicts efficacy of transdermal nicotine for smoking cessation. | 2006-06 |
|
| Regional and cellular distribution of CYP2E1 in monkey brain and its induction by chronic nicotine. | 2006-04 |
|
| Current status of immunologic approaches to treating tobacco dependence: vaccines and nicotine-specific antibodies. | 2006-02-24 |
|
| Attenuation of Abeta deposition in the entorhinal cortex of normal elderly individuals associated with tobacco smoking. | 2005-10 |
|
| Nicotine inhibits myofibroblast differentiation in human gingival fibroblasts. | 2005-08-15 |
|
| A therapeutic vaccine for nicotine dependence: preclinical efficacy, and Phase I safety and immunogenicity. | 2005-07 |
|
| Tobacco components stimulate Akt-dependent proliferation and NFkappaB-dependent survival in lung cancer cells. | 2005-07 |
|
| Cotinine, a neuroactive metabolite of nicotine: potential for treating disorders of impaired cognition. | 2005 |
|
| Determination of arecoline (areca nut alkaloid) and nicotine in hair by high-performance liquid chromatography/electrospray quadrupole mass spectrometry. | 2005 |
|
| Activation of platelets exposed to shear stress in the presence of smoke extracts of low-nicotine and zero-nicotine cigarettes: the protective effect of nicotine. | 2004-10 |
|
| Nicotine increases initial blood flow responses to local heating of human non-glabrous skin. | 2004-09-15 |
|
| The dopamine-containing neuron: maestro or simple musician in the orchestra of addiction? | 2003-04 |
|
| [The Tuaregs addiction to tea, to smokeless tobacco and to milk: ethnological and clinical approach]. | 2003-03-18 |
|
| Bacterial mutagenicity of some tobacco aromatic nitrogen bases and their mixtures. | 2001-05-31 |
|
| Plasma nitric oxide before and after smoking cessation with nicotine nasal spray. | 1998-01 |
|
| No acute effects of smoking and nicotine nasal spray on lipolysis measured by subcutaneous microdialysis. | 1997-06 |
|
| The maternal and fetal physiologic effects of nicotine. | 1996-04 |
|
| The effect of nicotine on in vitro sperm motion characteristics. | 1995-03 |
|
| Inhaled nicotine in humans: effect on the respiratory and cardiovascular systems. | 1994-06 |
|
| Simultaneous determination of nicotine and cotinine in various human tissues using capillary gas chromatography/mass spectrometry. | 1994 |
|
| Stereoselective metabolism of (S)-(-)-nicotine in humans: formation of trans-(S)-(-)-nicotine N-1'-oxide. | 1993-11-01 |
|
| 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. | 1985-12 |
|
| Cigarette smoking inhibits prostacyclin formation. | 1983-06-04 |
|
| NICOTINE-1'-OXIDE: A METABOLITE OF NICOTINE IN ANIMAL TISSUES. | 1964-07-20 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 12:27:06 GMT 2025
by
admin
on
Wed Apr 02 12:27:06 GMT 2025
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| Record UNII |
9R173T257I
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| Record Status |
Validated (UNII)
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491-26-9
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9R173T257I
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CHROMATOGRAPHIC PURITY (HPLC/UV)
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