2820-55-5

Usage

Uses

Used in Medical Research:
(2'S)-Nicotine 1-Oxide is used as a biomarker for bladder cancer in humans. The ratio of this metabolite to cotinine, another metabolite of nicotine, has been suggested as an indicator for the presence of bladder cancer.
Used in Pharmaceutical Industry:
(2'S)-Nicotine 1-Oxide is used as an intermediate compound in the synthesis of various nicotine-derived drugs. Its unique properties and metabolic origin make it a valuable compound for research and development in the pharmaceutical sector.
Used in Toxicology Studies:
(2'S)-Nicotine 1-Oxide is used as a subject of study in toxicology to understand the effects of nicotine and its metabolites on human health, particularly in the context of smoking and exposure to tobacco products.
Used in Analytical Chemistry:
(2'S)-Nicotine 1-Oxide serves as a reference compound in analytical chemistry for the development and validation of methods to detect and quantify nicotine and its metabolites in biological samples, such as blood, urine, and tissue.

InChI:InChI=1/C10H14N2O/c1-11-6-3-5-10(11)9-4-2-7-12(13)8-9/h2,4,7-8,10H,3,5-6H2,1H3

Upstream product

• 2055-29-0 (S)-(-)-nicotine-N,N'-dioxide 
• 54-11-5 nicotin 

Downstream Products

• 36508-80-2 (-)-Cotinine N-oxide 
• 112091-17-5 (S)-6-chloronicotine 
• 13270-56-9 (S)-6-Methylnicotine 
• 77698-47-6 (S)-2-methylnicotine 
• 101540-79-8 (S)-6-Methylnicotine 
• 64114-31-4 2-methylnicotine 

Relevant academic research and scientific papers

Reduction of amine N-oxides by diboron reagents

Facile reduction of alkylamino-, anilino-, and pyridyl-N-oxides can be achieved via the use of diboron reagents, predominantly bis- (pinacolato)- and in some cases bis(catecholato)diboron [(pinB)2 and (catB)2, respectively]. Reductions occur upon simply mixing the amine N oxide and the diboron reagent in a suitable solvent, at a suitable temperature. Extremely fast reductions of alkylamino- and anilino-N-oxides occur, whereas pyridyl-N-oxides undergo slower reduction. The reaction is tolerant of a variety of functionalities such as hydroxyl, thiol, and cyano groups, as well as halogens. Notably, a sensitive nucleoside N-oxide has also been reduced efficiently. The different rates with which alkylamino- and pyridyl-N-oxides are reduced has been used to perform stepwise reduction of the N,N-dioxide of (S)-(-)-nicotine. Because it was observed that (pinB)2 was unaffected by the water of hydration in amine oxides, the feasibility of using water as solvent was evaluated. These reactions also proceeded exceptionally well, giving high product yields. In constrast to the reactions with (pinB)2, triethylborane reduced alkylamino-N oxides, but pyridine N-oxide did not undergo efficient reduction even at elevated temperature. Finally, the mechanism of the reductive process by (pinB)2 has been probed by 1H and 11B NMR. (Figure presented) ; 2011 American Chemical Society.

6-Pyridylnicotine and bis-6,6'-nicotine - new chiral 2,2'-bipyridines

Starting from (-)-nicotine, two new 2,2'-bipyridine ligands 6 and 7 with chiral pyrrolidine side chains have been synthesized. The stoichiometric complexation by palladium(II) or mercury(II) ions gives the bipyridyl complexes 8 and 9.

REDUCTION OF N-OXIDE WITH BAKER'S YEAST

Reduction of N-oxides with baker's yeast has been examined.In the reduction of acetylpyridine N-oxides, selective reduction takes place to give chiral pyridylethanol N-oxides.