147732-31-8

Basic information

• Product Name: (R,S)-ortho-Cotinine
• Synonyms: (+/-)-ortho-Cotinine;o-Cotinine, 1-Methyl-2-oxo-5-(pyridin-2-yl)pyrrolidine
• CAS NO: 147732-31-8
• Molecular Formula: C10H12N2O
• Molecular Weight: 176.218
• Product Categories: Nicotine Derivatives;Heterocycles;Metabolites & Impurities;Mutagenesis Research Chemicals
• Mol File: 147732-31-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 120-135°C
• Flash Point: 167.9°C
• Appearance: /
• Density: 1.146g/cm³
• Vapor Pressure: 3.43E-05mmHg at 25°C
• Refractive Index: 1.555
• Storage Temp.: Amber Vial, Refrigerator
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Stability: Light Sensitive
• CAS DataBase Reference: (R,S)-ortho-Cotinine(CAS DataBase Reference)
• NIST Chemistry Reference: (R,S)-ortho-Cotinine(147732-31-8)
• EPA Substance Registry System: (R,S)-ortho-Cotinine(147732-31-8)

Safety Data

• Hazardous Substances Data: 147732-31-8(Hazardous Substances Data)

Usage

Description

(R,S)-ortho-Cotinine, also known as (+/-)-ortho-Cotinine, is a metabolite of nicotine in humans. It is characterized by its yellow oil appearance and is commonly used for internal standardization in the routine biomonitoring of nicotine metabolites.

Uses

Used in Biomonitoring:
(R,S)-ortho-Cotinine is used as an internal standard for the routine biomonitoring of nicotine metabolites. This application is crucial in ensuring accurate and reliable measurements of nicotine metabolites in various biological samples, such as blood, urine, or saliva.
Used in Pharmaceutical Research:
As a metabolite of nicotine, (R,S)-ortho-Cotinine plays a significant role in pharmaceutical research, particularly in the development of new drugs and therapies targeting nicotine addiction and related health issues. Its use as an internal standard aids in the accurate assessment of the effectiveness of these treatments.
Used in Toxicology Studies:
(R,S)-ortho-Cotinine is also utilized in toxicology studies to evaluate the potential health risks associated with nicotine exposure. By using (R,S)-ortho-Cotinine as an internal standard, researchers can more accurately determine the levels of nicotine metabolites in biological samples, which can help in understanding the toxicological effects of nicotine on the human body.
Used in Analytical Chemistry:
In the field of analytical chemistry, (R,S)-ortho-Cotinine serves as an essential internal standard for the quantification of nicotine metabolites. This application is vital in various research areas, including environmental monitoring, forensic toxicology, and the development of new analytical methods for the detection and quantification of nicotine and its metabolites.

InChI:InChI=1/C10H12N2O/c1-12-9(5-6-10(12)13)8-4-2-3-7-11-8/h2-4,7,9H,5-6H2,1H3

Upstream product

• 109-04-6 2-bromo-pyridine 
• 872-50-4 1-methyl-pyrrolidin-2-one 
• 109-09-1 2-chloropyridine 

Relevant articles and documents

Photocatalytic (Het)arylation of C(sp3)-H Bonds with Carbon Nitride

Graphitic carbon nitride materials have attracted significant interest in recent years and found applications in diverse light-to-energy conversions such as artificial photosynthesis, CO2 reduction, or degradation of organic pollutants. However, their utilization in synthetic photocatalysis, especially in the direct functionalization of C(sp3)-H bonds, remains underexplored. Herein, we report mesoporous graphitic carbon nitride (mpg-CN) as a heterogeneous organic semiconductor photocatalyst for direct arylation of C(sp3)-H bonds in combination with nickel catalysis. Our protocol has a broad synthetic scope (>70 examples including late-stage functionalization of drugs and agrochemicals), is operationally simple, and shows high chemo- and regioselectivities. Facile separation and recycling of the mpg-CN catalyst in combination with its low preparation cost, innate photochemical stability, and low toxicity are beneficial features overcoming typical shortcomings of homogeneous photocatalysis. Detailed mechanistic investigations and kinetic studies indicate that an unprecedented energy-transfer process (EnT) from the organic semiconductor to the nickel complex is operating.

Sp3 C-H Arylation and Alkylation Enabled by the Synergy of Triplet Excited Ketones and Nickel Catalysts

Triplet ketone sensitizers are of central importance within the realm of photochemical transformations. Although the radical-type character of triplet excited states of diaryl ketones suggests the viability for triggering hydrogen-atom transfer (HAT) and single-electron transfer (SET) processes, among others, their use as multifaceted catalysts in C-C bond-formation via sp3 C-H functionalization of alkane feedstocks still remains rather unexplored. Herein, we unlock a modular photochemical platform for forging C(sp3)-C(sp2) and C(sp3)-C(sp3) linkages from abundant alkane sp3 C-H bonds as functional handles using the synergy between nickel catalysts and simple, cheap and modular diaryl ketones. This method is distinguished by its wide scope that is obtained from cheap catalysts and starting precursors, thus complementing existing inner-sphere C-H functionalization protocols or recent photoredox scenarios based on iridium polypyridyl complexes. Additionally, such a platform provides a new strategy for streamlining the synthesis of complex molecules with high levels of predictable site-selectivity and preparative utility. Mechanistic experiments suggest that sp3 C-H abstraction occurs via HAT from the ketone triplet excited state. We believe this study will contribute to a more systematic utilization of triplet excited ketones as catalysts in metallaphotoredox scenarios.