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

Nitrefazole is an inhibitor of aldehyde dehydrogenase useful in the management of alcoholism. Cited advantages over disulfiram include longer duration of action, higher specificity (no inhibition of dopamine β-hydroxylase) and fewer side effects. It is generally recognized that the efficacy of such agents with respect to permanent abstinence is low. However, temporary abstinence and/or controlled drinking may facilitate supportive psychotherapy and/or delay the onset of severe alcoholic diseases.

Uses

Nitrefazole is a nitroimidazole derivative with the ability to inhibit aldehyde dehydrogenase, and enzyme crucial to the metabolism of alcohol. This compound is suitable for aldehyde dehydrogenase (ALDH) related research.

Brand name

ALTIMOL

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.