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
[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
| 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 |
|---|---|---|
| NICOTINE-1'-OXIDE: A METABOLITE OF NICOTINE IN ANIMAL TISSUES. | 1964 Jul 20 |
|
| 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 |
|
| Stereoselective metabolism of (S)-(-)-nicotine in humans: formation of trans-(S)-(-)-nicotine N-1'-oxide. | 1993 Nov-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 |
|
| Bacterial mutagenicity of some tobacco aromatic nitrogen bases and their mixtures. | 2001 May 31 |
|
| The dopamine-containing neuron: maestro or simple musician in the orchestra of addiction? | 2003 Apr |
|
| [The Tuaregs addiction to tea, to smokeless tobacco and to milk: ethnological and clinical approach]. | 2003 Jan-Feb |
|
| 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 Oct |
|
| Nicotine increases initial blood flow responses to local heating of human non-glabrous skin. | 2004 Sep 15 |
|
| Determination of arecoline (areca nut alkaloid) and nicotine in hair by high-performance liquid chromatography/electrospray quadrupole mass spectrometry. | 2005 |
|
| Nicotine inhibits myofibroblast differentiation in human gingival fibroblasts. | 2005 Aug 15 |
|
| Cotinine, a neuroactive metabolite of nicotine: potential for treating disorders of impaired cognition. | 2005 Autumn |
|
| A therapeutic vaccine for nicotine dependence: preclinical efficacy, and Phase I safety and immunogenicity. | 2005 Jul |
|
| Tobacco components stimulate Akt-dependent proliferation and NFkappaB-dependent survival in lung cancer cells. | 2005 Jul |
|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jul 07 00:06:09 UTC 2023
by
admin
on
Fri Jul 07 00:06:09 UTC 2023
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| Record UNII |
9R173T257I
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| Record Status |
Validated (UNII)
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| Record Version |
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142659
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DTXSID70867021
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491-26-9
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68107
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9R173T257I
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admin on Fri Jul 07 00:06:09 UTC 2023 , Edited by admin on Fri Jul 07 00:06:09 UTC 2023
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PARENT -> IMPURITY |
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