105650-23-5

Basic information

• Product Name: 2-AMINO-1-METHYL-6-PHENYLIMIDAZO[4,5-B]PYRIDINE
• Synonyms: 2-AMINO-1-METHYL-6-PHENYLIMIDAZO[4,5-B]PYRIDINE;PHIP;5-b)pyridin-2-amine,1-methyl-6-phenyl-1h-imidazo(;5-b)pyridine,2-amino-1-methyl-6-phenyl-1h-imidazo(;5-b)pyridine,2-amino-1-methyl-6-phenyl-imidazo(;Amino-1-methyl-6-phenylimidazo[4.5-b]pyridine;1-Methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-amine;2-AMINO-1-METHYL-6-PHENYLIMADAZO(4,5-B)PYRIDINE
• CAS NO: 105650-23-5
• Molecular Formula: C₁₃H₁₂N₄
• Molecular Weight: 224.26
• Product Categories: Detergents;Bases & Related Reagents;Mutagenesis Research Chemicals;Nucleotides
• Mol File: 105650-23-5.mol
• Article Data: 12

Chemical Properties

• Melting Point: 300
• Boiling Point: 355.66°C (rough estimate)
• Flash Point: 237.407 °C
• Appearance: Off-white solid
• Density: 1.2067 (rough estimate)
• Vapor Pressure: 5.74E-09mmHg at 25°C
• Refractive Index: 1.5890 (estimate)
• Storage Temp.: Refrigerator
• PKA: 7.72±0.30(Predicted)
• CAS DataBase Reference: 2-AMINO-1-METHYL-6-PHENYLIMIDAZO[4,5-B]PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-1-METHYL-6-PHENYLIMIDAZO[4,5-B]PYRIDINE(105650-23-5)
• EPA Substance Registry System: 2-AMINO-1-METHYL-6-PHENYLIMIDAZO[4,5-B]PYRIDINE(105650-23-5)

Safety Data

• Hazard Codes: T
• Hazardous Substances Data: 105650-23-5(Hazardous Substances Data)

Usage

Description

2-AMINO-1-METHYL-6-PHENYLIMIDAZO[4,5-B]PYRIDINE, also known as a mutagenic heterocyclic amine, is an imidazopyridine derivative with a methyl, amino, and phenyl group substitution at positions 1, 2, and 6, respectively. It is the most abundant of the mutagenic heterocyclic amines found in cooked meat and fish, and it is characterized by its off-white solid appearance.

Uses

Used in Carcinogen Research:
2-AMINO-1-METHYL-6-PHENYLIMIDAZO[4,5-B]PYRIDINE is used as a research compound for studying its carcinogenic properties. As a mutagenic heterocyclic amine, it is particularly relevant in understanding the mechanisms of cancer development and progression in individuals who consume cooked meat and fish.
Used in Food Industry:
In the food industry, 2-AMINO-1-METHYL-6-PHENYLIMIDAZO[4,5-B]PYRIDINE is used as a reference compound for monitoring and controlling the formation of potentially harmful substances during the cooking process. This helps to ensure food safety and quality, as well as to develop strategies for reducing the formation of such compounds in cooked meat and fish products.
Used in Pharmaceutical Industry:
Although not a direct pharmaceutical application, the study of 2-AMINO-1-METHYL-6-PHENYLIMIDAZO[4,5-B]PYRIDINE's properties and effects can contribute to the development of new drugs or therapies targeting cancer-related pathways. Understanding its mutagenic and carcinogenic properties can aid in the design of drugs that counteract or mitigate these effects, potentially leading to novel cancer treatments.

Safety Profile

Confirmed carcinogen with experimental carcinogenic data. Mutation data reported. When heated to decomposition it emits toxic vapors of NOx,.

Carcinogenicity

PhIP is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals and supporting genotoxicity data.

InChI:InChI=1/C13H12N4/c1-17-11-7-10(9-5-3-2-4-6-9)8-15-12(11)16-13(17)14/h2-8H,1H3,(H2,14,15,16)

Upstream product

• 506-68-3 bromocyane 
• 152684-14-5 3-methylamino-2-nitro-5-phenylpyridine 
• 107351-81-5 2-amino-3-methylamino-5-phenylpyridine 
• 125572-33-0 1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridine 
• 60-27-5 Creatinine 
• 22252-94-4 3-amino-2-phenylpropenal 
• 878996-00-0 2-amino-1-methylbenzothieno[3,2-e]imidazo[4,5-b]pyridine 
• 39827-52-6 2-aminobenzothiophene-3-carbaldehyde 
• 39827-54-8 2-azidobenzothiophene-3-carbaldehyde 
• 39856-98-9 bromo-2 formyl-3 <1>benzothiophene 
• 452-58-4 2,3-Diaminopyridine 
• 199442-68-7 N-(2-Amino-pyridin-3-yl)-4-methyl-benzenesulfonamide 
• 199442-69-8 N-(2-Amino-pyridin-3-yl)-4,N-dimethyl-benzenesulfonamide 
• 199442-70-1 N-(2-Amino-5-iodo-pyridin-3-yl)-4,N-dimethyl-benzenesulfonamide 

Downstream Products

• 150320-83-5 2-amino-1-methyl-6-[²H₅]-phenylimidazo[4,5-b]pyridine 
• 903905-79-3 N-[6-benzyloxy-9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-8-(1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-ylamino)-9H-purin-2-yl]-isobutyramide 
• 896719-53-2 6-benzyloxy-N²-[bis-(4-methoxy-phenyl)-phenyl-methyl]-9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-N⁸-(1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-yl)-9H-purine-2,8-diamine 
• 129018-59-3 2-nitro-1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridine 
• 944576-49-2 C₁₈H₂₀N₄O₂ 
• 124489-20-9 N-Hydroxy-PhIP 
• 896719-58-7 6-benzyloxy-9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-N⁸-(1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-yl)-9H-purine-2,8-diamine 
• 915092-62-5 2-amino-9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-8-(1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-ylamino)-1,9-dihydro-purin-6-one 
• 903905-86-2 N-[9-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-8-(1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-ylamino)-6-oxo-6,9-dihydro-1H-purin-2-yl]-isobutyramide 
• 358616-33-8 1-methyl-2-nitro-6-([2H]5-phenyl)-1H-imidazo[4,5-b]pyridine 
• 113638-87-2 4-Amino-N-[3-(1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-ylamino)-propyl]-benzamide 

Relevant articles and documents

Synthesis of a new isomer of creatinine and its use in the preparation of the food mutagen 2-amino-1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridine (PHIP)

Base-induced cyclization of N′-cyanomethyl-N′-methylurea gives 1-methyl-4-amino-imidazol-2-one, this in turn is condensed with 3-hydroxy-2-phenylacrolein to yield an imidazo[4,5-b]pyridine which is converted into 2-amino-1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridine (PHIP).

A test of the mutagenicity of cooked meats in vivo

There is a correlation between intestinal cancer and diets high in meat, so fried beef, chicken, lamb, pork and fish were tested for their ability to induce mutations in the small intestine of mice. The mice were bred to be heterozygous at the Dlb-1 locus so that loss of the dominant Dlb-1b allele by mutation could be detected. Mice were fed the AIN-76A diet (which contains 50% of the calories in the form of sucrose) or an isocaloric diet in which the sucrose was replaced by meat or fish, for 5 or 9 weeks. Manifestation of mutants requires ～1 week in this system, so this corresponds to an effective exposure of 4 and 8 weeks, respectively. There was no significant difference in the weights of animals on the different diets, and no difference in mutant frequency. Several food mutagens were present, but at low levels. These results, when considered in the light of tests of 2-amino-1-methyl-6-phenylimidazo[4,5-b] pyridine and amino(α)carboline at much higher doses (Zhang,X.-B., Tao,K.S., Urlando,C., Shaver-Walker,P. and Heddle,J.A. (1996) Mutagenesis, 11, 43-48), indicate that there is no highly mutagenic compound missed by previous testing with bacterial assays and that mixtures of heterocyclic amines at low levels do not show great synergy.

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.