21721-92-6

Basic information

• Product Name: 1-(4-NITROPHENYL)-2-METHYL-4-NITROIMIDAZOLE
• Synonyms: ALTIMOL;1-(4-NITROPHENYL)-2-METHYL-4-NITROIMIDAZOLE;EMD 15700;2-methyl-4-nitro-1-(4-nitrophenyl)-1h-imidazol;2-methyl-4-nitro-1-(4-nitrophenyl)imidazole;2-methyl-4-nitro-1-(p-nitrophenyl)-imidazol;bt-985;NITREFAZOLE
• CAS NO: 21721-92-6
• Molecular Formula: C₁₀H₈N₄O₄
• Molecular Weight: 248.19
• EINECS: 244-542-8
• Mol File: 21721-92-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 185-187°
• Boiling Point: 484.9°C at 760 mmHg
• Flash Point: 247.1°C
• Appearance: /
• Density: 1.53g/cm³
• Vapor Pressure: 1.48E-09mmHg at 25°C
• Refractive Index: 1.686
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly, Heated), DMSO (Slightly), Methanol (Slightly, Heated)
• CAS DataBase Reference: 1-(4-NITROPHENYL)-2-METHYL-4-NITROIMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-NITROPHENYL)-2-METHYL-4-NITROIMIDAZOLE(21721-92-6)
• EPA Substance Registry System: 1-(4-NITROPHENYL)-2-METHYL-4-NITROIMIDAZOLE(21721-92-6)

Safety Data

• Hazardous Substances Data: 21721-92-6(Hazardous Substances Data)

Usage

Description

1-(4-NITROPHENYL)-2-METHYL-4-NITROIMIDAZOLE, also known as Nitrefazole, is a nitroimidazole derivative with the ability to inhibit aldehyde dehydrogenase, an enzyme crucial to the metabolism of alcohol. It is recognized for its longer duration of action, higher specificity, and fewer side effects compared to other similar compounds. Nitrefazole is primarily used in the management of alcoholism and is available under the brand name ALTIMOL.

Uses

Used in Pharmaceutical Industry:
1-(4-NITROPHENYL)-2-METHYL-4-NITROIMIDAZOLE is used as an inhibitor of aldehyde dehydrogenase (ALDH) for the management of alcoholism. It offers advantages such as a longer duration of action, higher specificity (no inhibition of dopamine β-hydroxylase), and fewer side effects compared to other compounds like disulfiram.
Used in Research Applications:
Nitrefazole is used as a research compound for aldehyde dehydrogenase (ALDH) related studies. Its specificity and inhibitory properties make it a valuable tool in understanding the role of ALDH in alcohol metabolism and its potential applications in the development of treatments for alcoholism.

World Health Organization (WHO)

Nitrefazole, which is used in the treatment of alcoholism, was introduced in the early 1980s. By 1984 its use had been associated with hepatotoxic reactions, some of which were fatal. This led to its withdrawal in at least two countries. WHO has no information to suggest that preparations containing nitrefazole remain commercially available.

InChI:InChI=1/C10H8N4O4/c1-7-11-10(14(17)18)6-12(7)8-2-4-9(5-3-8)13(15)16/h2-6H,1H3

Upstream product

• 350-46-9 4-Fluoronitrobenzene 
• 73225-15-7 1-(4-nitrophenyl)-2-methylimidazole 

Relevant articles and documents

Synthesis and anti-tuberculosis activity of N-aryl-C-nitroazoles

Twelve N-aryl derivatives of 4-nitroimidazole, 2-methyl-4-nitroimidazole, 4-nitropyrazole or 3-nitro-1,2,4-triazole have been synthesized either by a degenerated ring transformation reaction of 1,4-dinitroimidazoles with 4-substituted anilines or by a condensation of fluoronitrobenzenes with salts prepared from C-nitro-1H-azoles and 1,8-diazabicyclo[5.4.0]-7-undecene. The Tuberculosis Antimicrobial Acquisition and Coordinating Facility has provided anti-mycobacterial data concerning inhibition activity of 12 compounds.