2-AMINO-1-METHYL-6-PHENYLIMIDAZO(4,5-B)PYRIDINE

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H12N4
Molecular Weight	224.2612
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 2-AMINO-1-METHYL-6-PHENYLIMIDAZO(4,5-B)PYRIDINE

Structure Search

SMILES

CN1C(N)=NC2=NC=C(C=C12)C3=CC=CC=C3

InChI

InChIKey=UQVKZNNCIHJZLS-UHFFFAOYSA-N

InChI=1S/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)

HIDE SMILES / InChI

Molecular Formula	C13H12N4
Molecular Weight	224.2612
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15110095 | https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:76290 | https://www.ncbi.nlm.nih.gov/pubmed/16908439

2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) is a mutagenic and carcinogenic heterocyclic amine formed during ordinary cooking, and is subsequently metabolically activated by cytochrome P4501A2 (CYP1A2) and N-acetyltransferase 2 (NAT2). PhIP has been used in trials studying the basic science of Pancreas Cancer.

Approval Year

PubMed

Title	Date	PubMed
Inhibition by white tea of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine-induced colonic aberrant crypts in the F344 rat.	2001	12094635
Meat consumption and risk of stomach cancer in Uruguay: a case-control study.	2001	11962244
Modulation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine-induced mutation in the cecum and colon of big blue rats by conjugated linoleic acid and 1,2-dithiole-3-thione.	2001	11759290
Functional characterization of nucleotide polymorphisms in the coding region of N-acetyltransferase 1.	2001 Aug	11505221
2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) modulates lactogenic hormone-mediated differentiation and gene expression in HC11 mouse mammary epithelial cells.	2001 Dec	11751460
Chemopreventive effects of ONO-8711, a selective prostaglandin E receptor EP(1) antagonist, on breast cancer development.	2001 Dec	11751431
Clean-up procedures for the analysis of heterocyclic aromatic amines (aminoazaarenes) from heat-treated meat samples.	2001 Dec 14	11771835
Intestinal tumorigenesis in multiple intestinal neoplasia mice induced by the food mutagen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine: perinatal susceptibility, regional variation, and correlation with DNA adducts.	2001 Dec 15	11751386
Detection of PhIP (2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine) in the milk of healthy women.	2001 Nov	11712910
Determination of 2-amino-1-methyl-6-phenylimidazo[4,5- b]pyridine (PhIP) and its metabolite 2-hydroxyamino-PhIP by liquid chromatography/electrospray ionization-ion trap mass spectrometry.	2001 Nov 15	11700987
Concentration of 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine (PhIP) in urine and alkali-hydrolyzed urine after consumption of charbroiled beef.	2001 Nov 8	11578808
Biochemical effects of dietary intakes of different broccoli samples. I. Differential modulation of cytochrome P-450 activities in rat liver, kidney, and colon.	2001 Oct	11586481
Lack of effect of furfural on unscheduled DNA synthesis in the in vivo rat and mouse hepatocyte DNA repair assays and in precision-cut human liver slices.	2001 Oct	11524138
The role of human glutathione S-transferases (hGSTs) in the detoxification of the food-derived carcinogen metabolite N-acetoxy-PhIP, and the effect of a polymorphism in hGSTA1 on colorectal cancer risk.	2001 Oct 1	11535243
Effect of cruciferous vegetable consumption on heterocyclic aromatic amine metabolism in man.	2001 Sep	11532863
Mutations induced by 2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine (PhIP) in cecum and proximal and distal colon of lacI transgenic rats.	2001 Sep	11507243
Cell transformation in vitro by food-derived heterocyclic amines Trp-P-1, Trp-P-2 and N(2)-OH-PhIP.	2001 Sep 14	11518607
Msh2 DNA mismatch repair gene deficiency and the food-borne mutagen 2-amino-1-methy1-6-phenolimidazo [4,5-b] pyridine (PhIP) synergistically affect mutagenesis in mouse colon.	2001 Sep 20	11593414
Chemoprevention of heterocyclic amine-induced mammary carcinogenesis in rats.	2002	11921198
2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP)-induced mutagenesis in cultured Big Blue rat mammary epithelial and fibroblast cells.	2002	11921195
Characterization of a major aromatic DNA adduct detected in human breast tissues.	2002	11921189
Carcinogen-DNA adducts in human breast epithelial cells.	2002	11921188
Mammary gland carcinogenesis by food-derived heterocyclic amines: metabolism and additional factors influencing carcinogenesis by 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP).	2002	11921185
Studies on mammary carcinogenesis induced by a heterocyclic amine, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, in mice and rats.	2002	11921184
Tobacco smoke carcinogens and breast cancer.	2002	11921179
Human exposure to heterocyclic amine food mutagens/carcinogens: relevance to breast cancer.	2002	11921178
Reduced Brca1 protein expression in 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine-induced rat mammary carcinomas.	2002 Aug	12203372
The food mutagen 2-amino-9H-pyrido[2,3-b]indole (AalphaC) but not its methylated form (MeAalphaC) increases intestinal tumorigenesis in neonatally exposed multiple intestinal neoplasia mice.	2002 Aug	12151357
Screening for heterocyclic amines in chicken cooked in various ways.	2002 Aug	12067585
Cafestol and kahweol, two coffee specific diterpenes with anticarcinogenic activity.	2002 Aug	12067578
Biomarkers of exposure to heterocyclic amines: approaches to improve the exposure assessment.	2002 Aug	12067575
Heterologous expression of human N-acetyltransferases 1 and 2 and sulfotransferase 1A1 in Salmonella typhimurium for mutagenicity testing of heterocyclic amines.	2002 Aug	12067565
Prevention by natural food anthocyanins, purple sweet potato color and red cabbage color, of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP)-associated colorectal carcinogenesis in rats initiated with 1,2-dimethylhydrazine.	2002 Feb	11915369
Antimutagenicity of Murdannia loriformis in the Salmonella mutation assay and its inhibitory effects on azoxymethane-induced DNA methylation and aberrant crypt focus formation in male F344 rats.	2002 Feb	11901756
Efficient induction of rat large intestinal tumors with a new spectrum of mutations by intermittent administration of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in combination with a high fat diet.	2002 Jan	11756241
Comparative tumorigenicity of the environmental pollutant 6-nitrochrysene and its metabolites in the rat mammary gland.	2002 Jul	12119009
Etiology-specific gene expression profiles in rat mammary carcinomas.	2002 Jul 1	12097258
Effects of dairy products on heterocyclic aromatic amine-induced rat colon carcinogenesis.	2002 Mar	11895863
Effect of conjugated linoleic acid on the formation of spontaneous and PhIP-induced mutation in the colon and cecum of rats.	2002 Mar 20	11890945
Mutagenic and carcinogenic heterocyclic amines as affected by muscle types/skin and cooking in pan-roasted mackerel.	2002 Mar 25	11909767
Antimutagenic activities of various lactic acid bacteria against food mutagens: heterocyclic amines.	2002 May	12222811
Induction of intestinal tumors and lymphomas in C57BL/6N mice by a food-borne carcinogen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine.	2002 May	12036442
Mutagenicity of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in the mammary gland of Big Blue rats on high-and low-fat diets.	2002 May	12016163
Oxidation of 5'-site guanine at GG and GGG sequences induced by a metabolite of carcinogenic heterocyclic amine PhIP in the presence of Cu(II) and NADH.	2002 May	12016160
Excretion of the N(2)-glucuronide conjugate of 2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine in urine and its relationship to CYP1A2 and NAT2 activity levels in humans.	2002 May	12016157
One dose of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) or 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) induces tumours in Min/+ mice by truncation mutations or LOH in the Apc gene.	2002 May 27	12034317
Natural variations of precursors in pig meat affect the yield of heterocyclic amines--effects of RN genotype, feeding regime, and sex.	2002 May 8	11982426
Single nucleotide instability: a wide involvement in human and rat mammary carcinogenesis?	2002 Sep 30	12351149
Molecular and genetic toxicology of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP).	2002 Sep 30	12351148
Suppression of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine-induced DNA damage in rat colon after grapefruit juice intake.	2002 Sep 8	12049810

Patents

Sample Use Guides

In Vivo Use Guide

Thirty minutes after oral or intravenous administration of PhIP (1 mg/kg), the PhIP levels in the small intestine were reduced 4- to 6-fold in Bcrp1;Mdr1a/b;Mrp2(-/) (-) and Bcrp1;Mrp2;Mrp3(-/-) mice compared with wild-type mice

Route of Administration: Other

In Vitro Use Guide

Asynchronized TK6 cells were harvested at various times after treatment with PhIP (1.25-10 ug/ml), fixed and stained with propidium iodide for the examination of cell cycle by fluorescence-activated flow cytometry.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:35:32 GMT 2023` Edited by `admin` on `Fri Dec 15 17:35:32 GMT 2023`
Record UNII	909C6UN66T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2-AMINO-1-METHYL-6-PHENYLIMIDAZO(4,5-B)PYRIDINE

Systematic Name

English

PHIP [IARC]

Common Name

English

AMINO-1-METHYL-6-PHENYLIMIDAZO(4,5-B)PYRIDINE, 2-

Systematic Name

English

2-AMINO-1-METHYL-6-PHENYL-1H-IMIDAZO(4,5-B)PYRIDINE

Systematic Name

English

1-METHYL-6-PHENYL-1H-IMIDAZO(4,5-B)PYRIDIN-2-AMINE

Systematic Name

English

2-AMINO-1-METHYL-6-PHENYLIMIDAZO(4,5-B)PYRIDINE [HSDB]

Common Name

English

1H-IMIDAZO(4,5-B)PYRIDIN-2-AMINE, 1-METHYL-6-PHENYL-

Systematic Name

English

PHIP [MI]

Common Name

English

PHIP	Locators: MI Sources:

Common Name

English

Code System Code Type Description

HSDB

7768