Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C10H14N2O |
| Molecular Weight | 178.231 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 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-JQWIXIFHSA-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
(1'S,2'S)-nicotine-1'-N-oxide is a stereoisomer of nicotine-1'-N-oxide, an oxidation product of S-(-)-nicotine. N-1'-oxidation of nicotine is mediated via flavin-containing monooxygenase. A marked stereoselectivity has been observed in the formation of N-1'-oxide metabolites from nicotine. Mammal hepatic preparations generally produce more the N-1'R,2'S-cis diastereoisomer than N-1'S,2'S-trans diastereoisomer after incubation with S-(-)-nicotine. (1'S,2'S)-nicotine-1'-N-oxide was reported to bind alpha3beta4 neuronal nicotinic acetylcholine receptor. cis- and trans-nicotine-N'-oxides modulate the development of tumors in rats initiated with N-[4-(5-nitro-2-furyl)-2-thiazolyl]formamide.
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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| In vitro-in vivo correlations of human (S)-nicotine metabolism. | 1995 Aug 8 |
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| Diastereospecific kinetics of nicotine N'-oxidation in rat liver microsomes. | 1998 Feb |
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| Screening of tobacco smoke condensate for nicotinic acetylcholine receptor ligands using cellular membrane affinity chromatography columns and missing peak chromatography. | 2008 Sep 29 |
Patents
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6V35J35GP5
Created by
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12313859
Created by
admin on Sat Dec 16 09:46:15 GMT 2023 , Edited by admin on Sat Dec 16 09:46:15 GMT 2023
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51095-86-4
Created by
admin on Sat Dec 16 09:46:15 GMT 2023 , Edited by admin on Sat Dec 16 09:46:15 GMT 2023
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PARENT (METABOLITE LESS ACTIVE)
SUBSTANCE RECORD
