65880-39-9

Basic information

• Product Name: 6-methyl-6H-indolo[2,3-b]quinoxaline
• Synonyms: 6H-Indolo[2,3-b]quinoxaline, 6-methyl-; 6-Methyl-6H-indolo(2,3-b)quinoxaline; 6-Methyl-6H-indolo[2,3-b]quinoxaline; 6-Methylindolo(2,3-b)quinoxaline
• CAS NO: 65880-39-9
• Molecular Formula: C₁₅H₁₁N₃
• Molecular Weight: 233.2679
• Mol File: 65880-39-9.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 461°C at 760 mmHg
• Flash Point: 232.6°C
• Density: 1.3g/cm³
• Vapor Pressure: 1.11E-08mmHg at 25°C
• Refractive Index: 1.726
• CAS DataBase Reference: 6-methyl-6H-indolo[2,3-b]quinoxaline(CAS DataBase Reference)
• NIST Chemistry Reference: 6-methyl-6H-indolo[2,3-b]quinoxaline(65880-39-9)
• EPA Substance Registry System: 6-methyl-6H-indolo[2,3-b]quinoxaline(65880-39-9)

Safety Data

• Hazardous Substances Data: 65880-39-9(Hazardous Substances Data)

Usage

General Description

6-methyl-6H-indolo[2,3-b]quinoxaline, also known as IQ or 6-MIQ, is a heterocyclic aromatic compound with a unique chemical structure. It is a potent mutagen and carcinogen that has been found in cooked meats and cigarette smoke. 6-MIQ is formed during the cooking process of meat, particularly when it is grilled or barbecued at high temperatures. Additionally, it is present in the smoke of cigarettes and has been linked to the development of cancer, particularly in the lungs and digestive system. The compound has been extensively studied due to its potential health risks, and efforts have been made to reduce its formation in food and tobacco products.

Upstream product

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• 74-88-4 methyl iodide 
• 91658-90-1 3-[(Z)-2-Amino-phenylimino]-1-methyl-1,3-dihydro-indol-2-one 
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• 868-85-9 Dimethyl phosphite 
• 201665-48-7 ethyl 3-{[(trifluoromethyl)sulfonyl]oxy}-1-methyl-1H-2-indolecarboxylate 
• 213920-65-1 6-methyl-6H-indolo[2,3-b]quinoxaline N-oxide 
• 213920-66-2 6-methyl-6H-indolo[2,3-b]quinoxaline-5,11-diium-5,11-diolate 

Relevant articles and documents

Indoloquinoxaline derivatives as promising multi-functional anti-Alzheimer agents

To confront a disease like Alzheimer’s disease having complex pathogenesis, development of multitarget-directed ligands has emerged as a promising drug discovery approach. In our endeavor towards the development of multitarget-directed ligands for Alzheimer’s disease, a series of indoloquinoxaline derivatives were designed and synthesized. In vitro cholinesterase inhibition studies revealed that all the synthesized compounds exhibited moderate to good cholinesterase inhibitory activity. 6-(6-(Piperidin-1-yl)hexyl)-6H-indolo[2,3-b]quinoxaline 9f was identified as the most potent and selective BuChE inhibitor (IC50 = 0.96 μM, selectivity index = 0.17) that possessed 2 fold higher BuChE inhibitory activity compared to the commercially approved reference drug donepezil (IC50 = 1.87 μM). Moreover, compound 9f is also endowed with self-induced Aβ1-42 aggregation inhibitory activity (51.24% inhibition at 50 μM concentration). Some of the compounds of the series also displayed moderate anti-oxidant activity. To perceive a putative binding mode of the compound 9f, molecular docking studies were carried out, and the results pointed out significant interactions of compound 9f with the enzymes in the binding sites of cholinesterases as well as Aβ1-42. Additionally, compound 9f exhibited favorable in silico ADMET properties. Put together these findings project compound 9f as a potential multitarget-directed ligand in the direction of developing novel anti-AD drugs. Communicated by Ramaswamy H. Sarma.

Cerium oxide nanoparticle-catalyzed three-component protocol for the synthesis of highly substituted novel quinoxalin-2-amine derivatives and 3,4-dihydroquinoxalin-2-amines in water

The syntheses of novel quinoxalin-2-amine derivatives were conducted in water using CeO2 nanoparticle catalyzed three-component reactions of 1,2-diamines with aldehydes and isocyanides. A variety of 3,4-dihydroquinoxalin- 2-amine derivatives we

A greener, facile and scalable synthesis of indole derivatives in water: Reactions of indole-2,3-diones with 1,2-difunctionalized benzene

An efficient, facile and greener protocol for the synthesis of indole derivatives viz., 3'H-spiro[indole- 3,2'-[1,3]benzothiazole]-2(1H)-ones, 6H-indolo[2,3-b]quinoxalines and 3-(2-hydroxy-phenylimino)- 1,3-dihydro-indol-2- ones, by the reactions of indol