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 |
|---|---|---|
| NICOTINE-1'-OXIDE: A METABOLITE OF NICOTINE IN ANIMAL TISSUES. | 1964 Jul 20 |
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| Cigarette smoking inhibits prostacyclin formation. | 1983 Jun 4 |
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| 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 |
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| Stereoselective metabolism of (S)-(-)-nicotine in humans: formation of trans-(S)-(-)-nicotine N-1'-oxide. | 1993 Nov-Dec |
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| Inhaled nicotine in humans: effect on the respiratory and cardiovascular systems. | 1994 Jun |
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| The effect of nicotine on in vitro sperm motion characteristics. | 1995 Mar |
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| 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 |
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| Determination of arecoline (areca nut alkaloid) and nicotine in hair by high-performance liquid chromatography/electrospray quadrupole mass spectrometry. | 2005 |
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| Tobacco components stimulate Akt-dependent proliferation and NFkappaB-dependent survival in lung cancer cells. | 2005 Jul |
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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 |
Patents
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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
Created by
admin on Sat Dec 16 18:51:42 GMT 2023 , Edited by admin on Sat Dec 16 18:51:42 GMT 2023
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SUBSTANCE RECORD
