491-26-9

Basic information

• Product Name: SNICOTINEN1OXIDE
• Synonyms: SNICOTINEN1OXIDE;(2S)-1-Methyl-2-(3-pyridyl)pyrrolidine 1-oxide;[2S,(-)]-1-Methyl-2α-(3-pyridinyl)pyrrolidine 1-oxide;3-[(2S)-1-methyl-1-oxidopyrrolidin-1-ium-2-yl]pyridine
• CAS NO: 491-26-9
• Molecular Formula: C₁₀H₁₄N₂O
• Molecular Weight: 178.26
• Mol File: 491-26-9.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: SNICOTINEN1OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: SNICOTINEN1OXIDE(491-26-9)
• EPA Substance Registry System: SNICOTINEN1OXIDE(491-26-9)

Safety Data

• Hazardous Substances Data: 491-26-9(Hazardous Substances Data)

Usage

Description

SNICOTINEN1OXIDE, also known as nicotine-N''-oxide, is a chemical compound derived from nicotine. It possesses unique properties that make it a versatile substance in various applications.

Uses

Used in Pharmaceutical Industry:
SNICOTINEN1OXIDE is used as a reactant for the preparation and cyanation of nicotine derivatives and analogs. It plays a crucial role in the synthesis of new compounds with potential therapeutic applications.
Used in Neuropharmacology:
SNICOTINEN1OXIDE is used as a stimulator for α7 nAChR (alpha 7 nicotinic acetylcholine receptor) and/or α4β2 receptors. These receptors are involved in various neurological processes, and modulation of their activity can have therapeutic benefits in treating certain conditions related to cognitive function and neurodegenerative diseases.

Hazard

A poison.

InChI:InChI=1/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

Upstream product

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

Downstream Products

• 15769-88-7 2'-Methyl-6'-(3-pyridyl)-tetrahydro-1',2'-oxazin 
• 42459-12-1 5'-cyanonicotine 
• 56895-68-2 1-methyl-2-(pyridin-3-yl)pyrrolidine-2-carbonitrile 
• 59-67-6 nicotinic acid 
• 22083-74-5 3-(1-methyl-pyrrolidin-2-yl)-pyridine 
• 54-11-5 nicotin 

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..

The biosynthesis of [5'-14C]cotinine and other radiolabeled nicotine metabolites

The present study describes the biosynthesis and isolation of the major radiolabeled nicotine metabolites formed using phenobarbitone (PB)-induced rabbit hepatic homogenates (10,000 g fraction). The optimal incubation and extraction methods for cotinine formation from non-labeled nicotine were established. The biosynthesis and isolation of [5'-14C]cotinine and other radiolabeled metabolites such as [2'-14C]nornicotine and [4-14C]-(3-pyridyl)-4-oxobutyric acid, from commercially available [2'-14C]nicotine, were carried out using the developed methods. Cotinine was isolated using preparative silica gel TLC, whereas the other metabolites were obtained using a cation-exchange HPLC method. This study showed that in addition to the two major metabolites (i.e. cotinine and nornicotine), 4-(3-pyridyl)-4-oxo-butyric acid, 3-hydroxycotinine, norcotinine, nicotine-1'-N-oxide and cotinine-1-N-oxide were also formed when PB-induced rabbit hepatic homogenates were used. Two further metabolites of unknown structure were detected. However, the isolation and further purification were only carried out on cotinine, nornicotine and 4-(3-pyridyl)-4-oxo-butyric acid.

Alkaloids of Voacanga. V. N-oxy-voacamine

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