34834-67-8

Basic information

• Product Name: 3-hydroxy-1-methyl-5-pyridin-3-yl-pyrrolidin-2-one
• Synonyms: 3-hydroxy-1-methyl-5-pyridin-3-yl-pyrrolidin-2-one;Hydroxycotinine;(3R,5S)-1-Methyl-3-hydroxy-5-(3-pyridyl)pyrrolidine-2-one;(3R,5S)-3-Hydroxy-1-methyl-5-(3-pyridinyl)pyrrolidin-2-one;(3'R,5'S)-trans-3'-Hydroxynicotinine;3-Hydroxy-1-methyl-5-(3-pyridinyl)-2-pyrrolidinone;Ccris 7628;(3R,5S)-3-Hydroxy-1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone
• CAS NO: 34834-67-8
• Molecular Formula: C₁₀H₁₂N₂O₂
• Molecular Weight: 192.22
• Product Categories: Chiral Reagents;Heterocycles;Metabolites & Impurities;Mutagenesis Research Chemicals;Nicotine Derivatives;Chiral Reagents, Heterocycles, Metabolites & Impurities, Nicotine Derivatives, Mutagenesis Research Chemicals
• Mol File: 34834-67-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 107-109°C
• Boiling Point: 416.5°Cat760mmHg
• Flash Point: 9℃
• Appearance: /
• Density: 1.275g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.592
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• PKA: 13.02±0.40(Predicted)
• CAS DataBase Reference: 3-hydroxy-1-methyl-5-pyridin-3-yl-pyrrolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxy-1-methyl-5-pyridin-3-yl-pyrrolidin-2-one(34834-67-8)
• EPA Substance Registry System: 3-hydroxy-1-methyl-5-pyridin-3-yl-pyrrolidin-2-one(34834-67-8)

Safety Data

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 16-36/37-45
• RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
• WGK Germany: 1
• Hazardous Substances Data: 34834-67-8(Hazardous Substances Data)

Usage

Description

3-Hydroxy-1-methyl-5-pyridin-3-yl-pyrrolidin-2-one, also known as trans-3'-Hydroxycotinine (3HC), is a metabolite of nicotine derived from the metabolism of cotinine by the CYP2A6 enzyme. It is an N-alkylpyrrolidine with a hydroxy group substitution at position C-3 and exists as the 3R,5S-diastereomer. 3-hydroxy-1-methyl-5-pyridin-3-yl-pyrrolidin-2-one is characterized by its off-white to pale-yellow solid appearance and is commonly found in the urine of smokers and users of other tobacco or nicotine products.

Uses

Used in Pharmaceutical Industry:
3-Hydroxy-1-methyl-5-pyridin-3-yl-pyrrolidin-2-one is used as a biomarker for [application reason] in the pharmaceutical industry. It is employed in nicotine testing methods and clinical and diagnostic testing of nicotine biomarkers by LC-MS/MS or GC/MS. 3-hydroxy-1-methyl-5-pyridin-3-yl-pyrrolidin-2-one serves as a valuable tool for studying tobacco and secondhand smoke exposure, as well as for developing pharmacological intervention strategies for smoking cessation.
Used in Research and Development:
In the research and development sector, 3-hydroxy-1-methyl-5-pyridin-3-yl-pyrrolidin-2-one is used as a key compound for understanding the metabolic pathways of nicotine and its effects on the human body. The study of this metabolite helps researchers gain insights into the role of CYP2A6 enzyme activity and its correlation with nicotine clearance from the body.
Used in Toxicology and Public Health:
3-Hydroxy-1-methyl-5-pyridin-3-yl-pyrrolidin-2-one is used as a toxicological marker and indicator of exposure to tobacco and nicotine products. Its presence in urine samples can help assess the extent of tobacco use and the potential health risks associated with it. This information is crucial for public health initiatives aimed at reducing tobacco consumption and its associated health hazards.
Used in Drug Metabolism Studies:
In the field of drug metabolism, 3-hydroxy-1-methyl-5-pyridin-3-yl-pyrrolidin-2-one is used as a model compound to study the role of specific enzymes, such as CYP2A6, in the metabolism of various drugs and substances. Understanding the metabolic pathways and enzyme interactions can lead to the development of more effective drugs and personalized treatment strategies.
Used in Environmental Monitoring:
3-Hydroxy-1-methyl-5-pyridin-3-yl-pyrrolidin-2-one can also be used in environmental monitoring to detect the presence of nicotine and other tobacco-related compounds in various settings, such as indoor air quality assessments and water quality evaluations. This information can help identify areas with high levels of secondhand smoke exposure and inform public health policies and interventions.

InChI:InChI=1/C10H12N2O2/c1-12-8(5-9(13)10(12)14)7-3-2-4-11-6-7/h2-4,6,8-9,13H,5H2,1H3/t8-,9?/m0/s1

Upstream product

• 126874-93-9 (3'R,5'S)-trans-3'-hydroxycotininyl hexanoate 
• 486-56-6 cotinine 
• 146275-16-3 (3R,5S)-1-methyl-3-benzoyloxy-5-(3-pyridyl)pyrrolidin-2-one 
• 500-22-1 3-pyridinecarboxaldehyde 
• 37096-14-3 cis-(3'S,5'S)-3'-hydroxycotinine 
• 796843-63-5 (2S)-N-[[(3S,5S)-3-(3-pyridyl)isoxazolidin-5-yl]carbonyl]bornane-10,2-sultam 
• 796843-65-7 (2S)-N-[[(3S,5S)-2-methyl-3-(3-pyridyl)isoxazolidin-5-yl]carbonyl]bornane-10,2-sultam 
• 796843-64-6 (2S)-N-[[(3S,5S)-2-ethoxymethyl-3-(3-pyridyl)isoxazolidin-5-yl]carbonyl]bornane-10,2-sultam 
• 205246-48-6 trans-3′-hydroxycotinine 
• 15569-85-4 cotinine 

Relevant articles and documents

Synthesis of (3′R,5′S)-3′-hydroxycotinine using 1,3-dipolar cycloaddition of a nitrone

To synthesize (3′R,5′S)-3′-hydroxycotinine [(+)-1], the main metabolite of nicotine (2), cycloaddition of C-(3-pyridyl)nitrones 3a, 3c, and 15 with (2R)- and (2S)-N-(acryloyl)bornane-10,2-sultam [(2R)- and (2S)-8] was examined. Among them, l-gulose-derived nitrone 15 underwent stereoselective cycloaddition with (2S)-8 to afford cycloadduct 16, which was elaborated to (+)-1. Graphical Abstract

METABOLIC STUDIES WITH MODEL CYTOCHROME p-450 SYSTEMS

The biomimetic potential of metalloporphyrin catalysts has been studied using nicotine as the substrate.Results indicate the formation of products identical to those obtained from in vivo metabolism.

Deuterium isotope effects in the in vivo metabolism of cotinine

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