51095-86-4

Basic information

• Product Name: (1'S,2'S)-NICOTINE 1'-OXIDE
• Synonyms: (1'S,2'S)-NICOTINE 1'-OXIDE;(1'S,2'S)-NICOTINE 1'-OXIDE AND (1'R,2'S)-NICOTINE 1'-OXIDE;(1'S,2'S)-TRANS-NICOTINE 1'-OXIDE;(1S,2S)-syn-Nicotine N'-oxide;(1'S,2'S)-trans-Nicotine-1'-N-oxide;(1S-cis)-3-(1-Methyl-1-oxido-2-pyrrolidinyl)pyridine;(1S-cis)-3-(1-Methyl-2-pyrrolidinyl)pyridine N-Oxide;3-[(1S,2S)-1-Methyl-1-oxido-2-pyrrolidinyl] pyridine
• CAS NO: 51095-86-4
• Molecular Formula: C₁₀H₁₄N₂O
• Molecular Weight: 178.23
• Product Categories: Nicotine Derivatives;Aromatics;Chiral Reagents;Heterocycles;Mutagenesis Research Chemicals;Nitric Oxide Reagents
• Mol File: 51095-86-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 182-183°C
• Appearance: /
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• CAS DataBase Reference: (1'S,2'S)-NICOTINE 1'-OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (1'S,2'S)-NICOTINE 1'-OXIDE(51095-86-4)
• EPA Substance Registry System: (1'S,2'S)-NICOTINE 1'-OXIDE(51095-86-4)

Safety Data

• Hazardous Substances Data: 51095-86-4(Hazardous Substances Data)

Usage

Chemical Properties

Off-White to Yellow Solid

Uses

Different sources of media describe the Uses of 51095-86-4 differently. You can refer to the following data:
1. Nicotine-1’-N-oxide is a derivative of nicotine found in the leaves, stems, and roots of N. tabacum, N. affinis and N. sylvestris. Nicotine-1’-N-oxide has also been identified as a metabolite of nicotine in animals and in man. The metabolism of nicotine
2. Nicotine-1’-N-oxide is a derivative of Nicotine (N412420) found in the leaves, stems, and roots of N. tabacum, N. affinis and N. sylvestris. Nicotine-1’-N-oxide has also been identified as a metabolite of nicotine in animals and in man. The metabolism of nicotine in man proceeds by alternative routes of oxidation of nitrogen to form nicotine-1’-N-oxide (both diastereomers) or cotinine. The ratio of these two products has been suggested as an indicator of bladder cancer in humans.

Synthetic route

nicotin (54-11-5) → (S)-(-)-Nicotine N-1'-oxide (51020-67-8) + trans-(S)-nicotine N-1'-oxide (51095-86-4)

Conditions	Yield
With dihydrogen peroxide
With rat liver microsomes In phosphate buffer at 37℃; for 0.0333333h; pH=8.4; Enzyme kinetics; Oxidation; Enzymatic reaction;
With dihydrogen peroxide Oxidation; Title compound not separated from byproducts;
With dihydrogen peroxide

acetic anhydride (108-24-7) + trans-(S)-nicotine N-1'-oxide (51095-86-4) → N-methyl-N-(4-oxo-4-[3]pyridyl-butyl)-acetamide (63551-23-5)

trans-(S)-nicotine N-1'-oxide (51095-86-4) → (S)-2-methyl-6-[3]pyridyl-tetrahydro-[1,2]oxazine (2055-26-7, 15769-88-7)

Conditions	Yield
at 190 - 200℃; under 1 Torr;
at 190 - 200℃; under 1 Torr;

trans-(S)-nicotine N-1'-oxide (51095-86-4) + 3-<2S)-1c-methyl-1t-oxy-pyrrolidin-2r-yl>-pyridine + fuming aqueous HCl → 4-(methylamino)-1-(3'-pyridyl)-1-butanone dihydrochloride (16426-44-1, 66093-90-1)

Conditions	Yield
at 140℃;

trans-(S)-nicotine N-1'-oxide (51095-86-4) → (S)-4-methylamino-1-[3]pyridyl-butan-1-ol (2055-27-8, 76030-54-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 190 - 200 °C / 1 Torr 2: zinc-powder; acetic acid View Scheme

trans-(S)-nicotine N-1'-oxide (51095-86-4) → 4-(methylamino)-1-(3'-pyridyl)-1-butanone dihydrochloride (16426-44-1, 66093-90-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 190 - 200 °C / 1 Torr 2: concentrated aqueous HCl / 140 °C View Scheme

Upstream product

• 22083-74-5 3-(1-methyl-pyrrolidin-2-yl)-pyridine 
• 54-11-5 nicotin 

Downstream Products

• 22083-74-5 3-(1-methyl-pyrrolidin-2-yl)-pyridine 
• 16426-44-1 4-(methylamino)-1-(3'-pyridyl)-1-butanone dihydrochloride 
• 42459-12-1 5'-cyanonicotine 
• 56895-68-2 1-methyl-2-(pyridin-3-yl)pyrrolidine-2-carbonitrile 
• 54-11-5 nicotin 
• 59-67-6 nicotinic acid 
• 15769-88-7 2'-Methyl-6'-(3-pyridyl)-tetrahydro-1',2'-oxazin 
• 2055-26-7 (S)-2-methyl-6-[3]pyridyl-tetrahydro-[1,2]oxazine 
• 63551-23-5 1'-(3-Pyridyl)-4'-(N'-acetylmethylamino)-1'-propanon 
• 2055-27-8 (S)-4-methylamino-1-[3]pyridyl-butan-1-ol 

Relevant articles and documents

Racemic synthesis of 2′-substituted nicotine analogs

The chemical and pharmacological properties of 2′-substituted nicotines are poorly understood relative to other substituted nicotines. We developed a practical synthesis of the key intermediate (6)-2′- cyanonicotine using the Polonovski reaction. Alkylation of (6)-2′- cyanonicotine with Grignard reagents led to several 2′-alkylnicotines; (6)-2′-aminomethylnicotine, (6)-2′-hydroxymethylnicotine, and (6)-2′- carbamoylnicotine were also synthesized..

First asymmetric oxidation of tertiary amines by cyclohexanone monooxygenase

Cyclohexanone monooxygenase catalyzes the asymmetric oxidation of some tertiary amines to amine N-oxides. The structure of the amine markedly influences the enantiomeric excess of products.

Diastereospecific kinetics of nicotine N'-oxidation in rat liver microsomes

1. In kinetic studies, both Eadie-Hofstee plots for cis- and trans-nicotine-1'-N-oxide formation from nicotine in rat liver microsomes were linear. For the formation of cis- and trans-nicotine-1'-N-oxide, the apparent k(m) were 0.240 ± 0.069 and 1.524 ± 0.951 mM respectively. Corresponding V(max) were 1.52 ± 0.48 and 1.19 ± 0.74 nmol/mg/min respectively. 2. The formation of cis-nicotine-1'-N-oxide was greater than the formation of trans-nicotine-1'-N-oxide in rat liver microsomes and the intrinsic clearance of cis-nicotine-1'-N-oxide formation was 8.1-fold greater than that of trans-nicotine-1'-N-oxide formation. 3. The formation of both cis- and trans-nicotine-1'-N-oxide in rat liver microsomes was inhibited by the addition of 1-(1-naphthyl)-2-thiourea or by heat-treatment of microsomes. 2-Diethylaminoethyl-2, 2-diphenylvalerate (SKF525A) and carbon monoxide did not affect these activities even at high concentrations. 4. Formations of cis- and trans-nicotine-1'-N-oxide correlated significantly with each other (r = 0.862, p 0.01). These results suggested that the same flavin-containing monooxygenase (FMO) isoform is responsible for the formation of cis- and trans-nicotine-1'-N-oxide in rat liver.