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
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 |
|---|---|---|
| Stereoselective metabolism of (S)-(-)-nicotine in humans: formation of trans-(S)-(-)-nicotine N-1'-oxide. | 1993 Nov-Dec |
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| The effect of nicotine on in vitro sperm motion characteristics. | 1995 Mar |
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| The maternal and fetal physiologic effects of nicotine. | 1996 Apr |
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| No acute effects of smoking and nicotine nasal spray on lipolysis measured by subcutaneous microdialysis. | 1997 Jun |
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| Plasma nitric oxide before and after smoking cessation with nicotine nasal spray. | 1998 Jan |
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| Nicotine increases initial blood flow responses to local heating of human non-glabrous skin. | 2004 Sep 15 |
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| Nicotine inhibits myofibroblast differentiation in human gingival fibroblasts. | 2005 Aug 15 |
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| Cotinine, a neuroactive metabolite of nicotine: potential for treating disorders of impaired cognition. | 2005 Autumn |
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| A therapeutic vaccine for nicotine dependence: preclinical efficacy, and Phase I safety and immunogenicity. | 2005 Jul |
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| Tobacco components stimulate Akt-dependent proliferation and NFkappaB-dependent survival in lung cancer cells. | 2005 Jul |
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| Attenuation of Abeta deposition in the entorhinal cortex of normal elderly individuals associated with tobacco smoking. | 2005 Oct |
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| Regional and cellular distribution of CYP2E1 in monkey brain and its induction by chronic nicotine. | 2006 Apr |
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| Nicotine metabolite ratio predicts efficacy of transdermal nicotine for smoking cessation. | 2006 Jun |
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| [Development of analytical method for determination nicotine metabolites in urine]. | 2009 |
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| UGT2B10 genotype influences nicotine glucuronidation, oxidation, and consumption. | 2010 Jun |
Patents
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| Code System | Code | Type | Description | ||
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142659
Created by
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DTXSID70867021
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491-26-9
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68107
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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
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SUBSTANCE RECORD
