30458-69-6

Basic information

• Product Name: 2-AMINO-3-METHYLIMIDAZO(4,5-B)PYRIDINE
• Synonyms: 2-AMINO-3-METHYLIMIDAZO(4,5-B)PYRIDINE;3-Methyl-3H-IMidazo[4,5-b]pyridin-2-aMine
• CAS NO: 30458-69-6
• Molecular Formula: C7H8 N4
• Molecular Weight: 148.17
• Mol File: 30458-69-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 220-221 °C(Solv: ethanol (64-17-5))
• Boiling Point: 356.1°Cat760mmHg
• Flash Point: 169.1°C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 3E-05mmHg at 25°C
• Refractive Index: 1.727
• PKA: 7.62±0.30(Predicted)
• CAS DataBase Reference: 2-AMINO-3-METHYLIMIDAZO(4,5-B)PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-3-METHYLIMIDAZO(4,5-B)PYRIDINE(30458-69-6)
• EPA Substance Registry System: 2-AMINO-3-METHYLIMIDAZO(4,5-B)PYRIDINE(30458-69-6)

Safety Data

• Hazardous Substances Data: 30458-69-6(Hazardous Substances Data)

Usage

General Description

2-Amino-3-methylimidazo(4,5-b)pyridine, also known as PhIP, is a chemical compound formed during the cooking of meat, poultry, and fish at high temperatures. It is classified as a heterocyclic amine and is considered a potential human carcinogen. PhIP has been identified as a mutagen and has been shown to induce tumors in laboratory animals. It is metabolized in the body to form reactive intermediates that can damage DNA and lead to the development of cancer. Exposure to PhIP has been linked to an increased risk of certain types of cancer, particularly in the colon, breast, and prostate. As a result, efforts are being made to reduce human exposure to PhIP, such as through changes in cooking practices and the development of methods to detect and remove PhIP from cooked foods.

InChI:InChI=1/C7H8N4/c1-11-6-5(10-7(11)8)3-2-4-9-6/h2-4H,1H3,(H2,8,10)

Upstream product

• 5470-18-8 2-Chloro-3-nitropyridine 
• 506-68-3 bromocyane 
• 5028-20-6 3-amino-2-methylaminopyridine 
• 4093-88-3 2-(methylamino)-3-nitropyridine 
• 1097725-72-8 3-methyl-2-N-(p-toluenesulfonyl)aminoimidazo[4,5-b]pyridine 
• 30458-68-5 2-chloro-3-methyl-3H-imidazo[4,5-b]pyridine 
• 21991-39-9 3-methyl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one 
• 6298-19-7 2-chloro-3-aminopyridine 

Relevant articles and documents

Discovery of iminobenzimidazole derivatives as novel cytotoxic agents

In our quest to identify inhibitors of the eukaryotic translation initiation factor 4F (eIF4F), we serendipitously discovered a novel cytotoxic agent. Even though this compound did not inhibit translation, we explored the structural requirements for its cytotoxicity due to its structural originality. A series of 1,3-disubstituted iminobenzimidazoles was synthesized and evaluated for their in vitro cytotoxicity. The structure-activity relationship studies demonstrate that hydrophobic substituent is essential for activity. The most active compounds displayed a cytotoxicity in KB, HL60 and HCT116 human cancer cells with an IC50 of about 1μM. These first-in-class series of low molecular weight synthetic molecules may provide the basis for the development of new anticancer drugs.

Synthesis and mutagenic potency of structural isomers of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine

(Chemical Equation Presented) Synthesis of 2-amino-1-methyl-6- phenylimidazo[4,5-b]pyridine (PhIP), three structural isomers, and two desphenyl PhIP congeners has been carried out. Mutagenic potency was evaluated using S. typhimurium strain TA98 in the Ames test. Mutagenic potency increased in relation to structural features in these heterocyclic amines that allow extended resonance between the phenyl and imidazo[4,5-b]pyridine N2-amino substituents. By contrast, PhIP isomers, whose substitution disallows involvement of the phenyl group in their ammoimidazo resonance hybrids, and desphenyl congeners were from 86- to 234-fold less mutagenic than PhIP.