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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

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

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

PubMed

TitleDatePubMed
Inhibition by white tea of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine-induced colonic aberrant crypts in the F344 rat.
2001
Meat consumption and risk of stomach cancer in Uruguay: a case-control study.
2001
Comparison of the mutagenic responses of mismatch repair-proficient (TK6) and mismatch repair-deficient (MT1) human lymphoblast cells to the food-borne carcinogen PhIP.
2001
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
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
Chemopreventive effects of ONO-8711, a selective prostaglandin E receptor EP(1) antagonist, on breast cancer development.
2001 Dec
Clean-up procedures for the analysis of heterocyclic aromatic amines (aminoazaarenes) from heat-treated meat samples.
2001 Dec 14
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
Detection of PhIP (2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine) in the milk of healthy women.
2001 Nov
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
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
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
Sex-specific induction of mutations by PhIP in the kidney of male and female rats and its modulation by conjugated linoleic acid.
2002
Chemoprevention of heterocyclic amine-induced mammary carcinogenesis in rats.
2002
2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP)-induced mutagenesis in cultured Big Blue rat mammary epithelial and fibroblast cells.
2002
Characterization of a major aromatic DNA adduct detected in human breast tissues.
2002
Carcinogen-DNA adducts in human breast epithelial cells.
2002
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
Studies on mammary carcinogenesis induced by a heterocyclic amine, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, in mice and rats.
2002
Tobacco smoke carcinogens and breast cancer.
2002
Human exposure to heterocyclic amine food mutagens/carcinogens: relevance to breast cancer.
2002
Inhibition of conjugated fatty acids derived from safflower or perilla oil of induction and development of mammary tumors in rats induced by 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP).
2002 Apr 25
Reduced Brca1 protein expression in 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine-induced rat mammary carcinomas.
2002 Aug
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
Screening for heterocyclic amines in chicken cooked in various ways.
2002 Aug
Cafestol and kahweol, two coffee specific diterpenes with anticarcinogenic activity.
2002 Aug
Biomarkers of exposure to heterocyclic amines: approaches to improve the exposure assessment.
2002 Aug
Heterologous expression of human N-acetyltransferases 1 and 2 and sulfotransferase 1A1 in Salmonella typhimurium for mutagenicity testing of heterocyclic amines.
2002 Aug
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
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
Chemoprevention of 2-amino-1-methyl-6-phenylimidazo- [4,5-b]pyridine-induced colon carcinogenesis by 1-O-hexyl-2,3,5-trimethylhydroquinone after initiation with 1,2-dimethylhydrazine in F344 rats.
2002 Feb
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
Differential metabolism of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in rat and human hepatocytes.
2002 Jan
Human prostate epithelial cells metabolize chemicals of dietary origin to mutagens.
2002 Jan 25
Comparative tumorigenicity of the environmental pollutant 6-nitrochrysene and its metabolites in the rat mammary gland.
2002 Jul
Etiology-specific gene expression profiles in rat mammary carcinomas.
2002 Jul 1
Effects of dairy products on heterocyclic aromatic amine-induced rat colon carcinogenesis.
2002 Mar
Effect of conjugated linoleic acid on the formation of spontaneous and PhIP-induced mutation in the colon and cecum of rats.
2002 Mar 20
Mutagenic and carcinogenic heterocyclic amines as affected by muscle types/skin and cooking in pan-roasted mackerel.
2002 Mar 25
Antimutagenic activities of various lactic acid bacteria against food mutagens: heterocyclic amines.
2002 May
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
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
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
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
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
Natural variations of precursors in pig meat affect the yield of heterocyclic amines--effects of RN genotype, feeding regime, and sex.
2002 May 8
Effects of cacao liquor proanthocyanidins on PhIP-induced mutagenesis in vitro, and in vivo mammary and pancreatic tumorigenesis in female Sprague-Dawley rats.
2002 Nov 28
Single nucleotide instability: a wide involvement in human and rat mammary carcinogenesis?
2002 Sep 30
Molecular and genetic toxicology of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP).
2002 Sep 30
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
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: 71 human volunteers consumpted either a high (7.4 ng/g) or low (1.7 ng/g) dose of PhIP. https://www.ncbi.nlm.nih.gov/pubmed/15110095
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
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 Thu Jul 06 00:54:21 UTC 2023
Edited
by admin
on Thu Jul 06 00:54:21 UTC 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
HSDB  
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
MI  
Common Name English
Code System Code Type Description
HSDB
7768
Created by admin on Thu Jul 06 00:54:21 UTC 2023 , Edited by admin on Thu Jul 06 00:54:21 UTC 2023
PRIMARY
CAS
105650-23-5
Created by admin on Thu Jul 06 00:54:21 UTC 2023 , Edited by admin on Thu Jul 06 00:54:21 UTC 2023
PRIMARY
PUBCHEM
1530
Created by admin on Thu Jul 06 00:54:21 UTC 2023 , Edited by admin on Thu Jul 06 00:54:21 UTC 2023
PRIMARY
WIKIPEDIA
2-Amino-1-methyl-6-phenylimidazo(4,5-b)pyridine
Created by admin on Thu Jul 06 00:54:21 UTC 2023 , Edited by admin on Thu Jul 06 00:54:21 UTC 2023
PRIMARY
CHEBI
76290
Created by admin on Thu Jul 06 00:54:21 UTC 2023 , Edited by admin on Thu Jul 06 00:54:21 UTC 2023
PRIMARY
MERCK INDEX
M8705
Created by admin on Thu Jul 06 00:54:21 UTC 2023 , Edited by admin on Thu Jul 06 00:54:21 UTC 2023
PRIMARY Merck Index
DRUG BANK
DB08398
Created by admin on Thu Jul 06 00:54:21 UTC 2023 , Edited by admin on Thu Jul 06 00:54:21 UTC 2023
PRIMARY
MESH
C049584
Created by admin on Thu Jul 06 00:54:21 UTC 2023 , Edited by admin on Thu Jul 06 00:54:21 UTC 2023
PRIMARY
EPA CompTox
DTXSID3037628
Created by admin on Thu Jul 06 00:54:21 UTC 2023 , Edited by admin on Thu Jul 06 00:54:21 UTC 2023
PRIMARY
NCI_THESAURUS
C29792
Created by admin on Thu Jul 06 00:54:21 UTC 2023 , Edited by admin on Thu Jul 06 00:54:21 UTC 2023
PRIMARY
FDA UNII
909C6UN66T
Created by admin on Thu Jul 06 00:54:21 UTC 2023 , Edited by admin on Thu Jul 06 00:54:21 UTC 2023
PRIMARY
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METABOLIC ENZYME -> SUBSTRATE
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Heterocyclic amine in cooked meat sample. 857?100 pg/g sample.
PARENT -> CONSTITUENT ALWAYS PRESENT
Heterocyclic amine in cooked meat sample 289?37 pg/g sample.
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Related Record Type Details
METABOLITE -> PARENT
MAJOR
METABOLITE TOXIC -> PARENT
Putative mutagenic metabolite. Reacts with DNA.
METABOLITE TOXIC -> PARENT
Mutagenic metabolite that reacts with DNA.
METABOLITE -> PARENT