21979-19-1

Usage

Quinolinium salt

A quinoline ring structure with a positively charged nitrogen atom
The compound has a quinoline ring structure that includes a nitrogen atom with a positive charge, making it a quinolinium salt.

1-Methyl substitution

A methyl group attached to the first carbon atom of the quinoline ring
The 1-methyl substitution refers to the presence of a methyl group (CH3) attached to the first carbon atom in the quinoline ring, giving the compound its unique properties.

Organic synthesis reagent

Used in the synthesis of pharmaceutical and natural products
1-methylquinolinium is commonly used as a reagent in organic synthesis, particularly for the production of various pharmaceutical and natural products.

Research precursor

For the synthesis of bioactive compounds
In research, 1-methylquinolinium serves as a precursor for the synthesis of bioactive compounds, which can have potential applications in medicine and other fields.

Starting material

For the preparation of dyes and fluorescent probes
The compound is also used as a starting material for the preparation of dyes and fluorescent probes, which are important tools in scientific research and diagnostics.

Wide range of applications

In the field of organic chemistry
1-methylquinolinium has a wide range of applications in organic chemistry, making it an important building block for the synthesis of various complex molecules.

InChI:InChI=1/C10H10N.ClH/c1-11-8-4-6-9-5-2-3-7-10(9)11;/h2-8H,1H3;1H/q+1;/p-1

Upstream product

• 91-22-5 quinoline 
• 77-78-1 dimethyl sulfate 
• 112033-50-8 N-cyclopropyl-N-methylphenylamine 
• 485-80-3 S-adenosyl-L-methionine 
• 74-88-4 methyl iodide 

Downstream Products

• 16021-60-6 1-Methyl-1,2-dihydroquinoline 
• 30958-75-9 1-methyl-1,4-dihydroquinoleine 
• 34161-94-9 N-(2-formylphenyl)-N,4-dimethylbenzenesulfonamide 
• 7755-70-6 2-(methylamino)benzaldehyde 

Relevant academic research and scientific papers

A Rapid and Efficient Assay for the Characterization of Substrates and Inhibitors of Nicotinamide N-Methyltransferase

Nicotinamide N-methyltransferase (NNMT) is one of the most abundant small molecule methyltransferases in the human body and is primarily responsible for the N-methylation of the nicotinamide (vitamin B3). Employing the cofactor S-adenosyl-l-methionine, NNMT transfers a methyl group to the pyridine nitrogen of nicotinamide to generate N-methylnicotinamide. Interestingly, NNMT is also able to N-methylate a variety of other pyridine-containing small molecules, suggesting a secondary role for the enzyme in the detoxification of xenobiotics. A number of recent studies have also revealed links between NNMT overexpression and a variety of diseases, including multiple cancers, Parkinson's disease, diabetes, and obesity. To facilitate further study of both the substrate scope and potential for inhibitor development, we here describe the development of a new NNMT activity assay. The assay makes use of ultra-high-performance hydrophilic interaction chromatography, allowing for rapid separation of the reaction products, coupled with quadrupole time-of-flight mass spectrometric detection, providing for enhanced sensitivity and enabling high-throughput sample analysis. We successfully demonstrated the general applicability of the method by performing kinetic analyses of NNMT-mediated methylation for a range of pyridine-based substrates. These findings also provide new insight into the diversity of substrate recognition by NNMT in a quantitative manner. In addition, we further established the suitability of the assay for the identification and characterization of small molecule inhibitors of NNMT. To do so, we investigated the inhibition of NNMT by the nonspecific methyltransferase inhibitors sinefungin and S-adenosyl-l-homocysteine, revealing IC50 values in the low micromolar range. The results of these inhibition studies are particularly noteworthy as they will permit future efforts toward the development of new NNMT-specific inhibitors.

Novel functionalization of 1-methyl-2-quinolone; dimerization and denitration of trinitroquinolone

New methods for functionalization of 1-methyl-2-quinolone (MeQoe) skeleton are provided. The reaction of 1-methyl-3,6,8-trinitro-2-quinolone (TNQ) with amines affords quinolone dimer 1 and 6,8-dinitroquinolone (6,8-DNQ). Dimerization predominantly proceed

Expedient synthesis of novel coumarin-based sulfonamides

The synthesis of novel coumarin-based sulfonamides was accomplished in good yields via InCl3-catalyzed three-component condensation of N-(2-formylphenyl)-N-methylbenzenesulfonamides, 4-hydroxycoumarin and cyclic secondary amines in toluene.

N-dealkylation of an N-cyclopropylamine by horseradish peroxidase. Fate of the cyclopropyl group

Cyclopropylamines inactivate cytochrome P450 enzymes which catalyze their oxidative N-dealkylation. A key intermediate in both processes is postulated to be a highly reactive aminium cation radical formed by single electron transfer (SET) oxidation of the nitrogen center, but direct evidence for this has remained elusive. To address this deficiency and identify the fate of the cyclopropyl group lost upon N-dealkylation, we have investigated the oxidation of N-cyclopropyl-N-methylaniline (3) by horseradish peroxidase, a well-known SET enzyme. For comparison, similar studies were carried out in parallel with N-isopropyl-N-methylaniline (9) and N,N-dimethylaniline (8). Under standard peroxidatic conditions (HRP, H2O2, air), HRP oxidizes 8 completely to N-methylaniline (4) plus formaldehyde within 15-30 min, whereas 9 is oxidized more slowly (14C]-3, [1′-13C]-3, and [2′,3′-13C]-3 as substrates, radiochemical and NMR analyses of incubation mixtures revealed that the complete oxidation of 3 by HRP yields 4 (0.2 mol), β-hydroxypropionic acid (17, 0.2 mol), and N-methylquinolinium (16, 0.8 mol). In buffer purged with pure O2, the complete oxidation of 3 yields 4 (0.7 mol), 17 (0.7 mol), and 16 (0.3 mol), while under anaerobic conditions, 16 is formed quantitatively from 3. These results indicate that the aminium ion formed by SET oxidation of 3 undergoes cyclopropyl ring fragmentation exclusively to generate a distonic cation radical (14+?) which then partitions between unimolecular cyclization (leading, after further oxidation, to 16) and bimolecular reaction with dissolved oxygen (leading to 4 and 17 in a 1:1 ratio). Neither β-hydroxypropionaldehyde, acrolein, nor cyclopropanone hydrate are formed as SET metabolites of 3. The synthetic and analytical methods developed in the course of these studies should facilitate the application of cyclopropylamine-containing probes to reactions catalyzed by cytochrome P450 enzymes.