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
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL1641355 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8908363 |
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Target ID: CHEMBL1808 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19065315 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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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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Simultaneous determination of nicotine and cotinine in various human tissues using capillary gas chromatography/mass spectrometry. | 1994 |
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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 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11974
Unknown
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23318728
Nicotine-1'-N-oxide (1-10 μM) weakly inhibited human platelets adhesion to fibrinogen
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 18:51:42 UTC 2023
by
admin
on
Sat Dec 16 18:51:42 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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CHROMATOGRAPHIC PURITY (HPLC/UV)
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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