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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=C1C=C(C=N2)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

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

Unknown
149124
PubMed

PubMed

TitleDatePubMed
Effects of cacao liquor proanthocyanidins on PhIP-induced mutagenesis in vitro, and in vivo mammary and pancreatic tumorigenesis in female Sprague-Dawley rats.
2002-11-28
Single nucleotide instability: a wide involvement in human and rat mammary carcinogenesis?
2002-09-30
Molecular and genetic toxicology of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP).
2002-09-30
Suppression of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine-induced DNA damage in rat colon after grapefruit juice intake.
2002-09-08
Reduced Brca1 protein expression in 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine-induced rat mammary carcinomas.
2002-08
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.
2002-08
Screening for heterocyclic amines in chicken cooked in various ways.
2002-08
Cafestol and kahweol, two coffee specific diterpenes with anticarcinogenic activity.
2002-08
Biomarkers of exposure to heterocyclic amines: approaches to improve the exposure assessment.
2002-08
Heterologous expression of human N-acetyltransferases 1 and 2 and sulfotransferase 1A1 in Salmonella typhimurium for mutagenicity testing of heterocyclic amines.
2002-08
Etiology-specific gene expression profiles in rat mammary carcinomas.
2002-07-01
Comparative tumorigenicity of the environmental pollutant 6-nitrochrysene and its metabolites in the rat mammary gland.
2002-07
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.
2002-05-27
Natural variations of precursors in pig meat affect the yield of heterocyclic amines--effects of RN genotype, feeding regime, and sex.
2002-05-08
Antimutagenic activities of various lactic acid bacteria against food mutagens: heterocyclic amines.
2002-05
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.
2002-05
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.
2002-05
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.
2002-05
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.
2002-05
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).
2002-04-25
Mutagenic and carcinogenic heterocyclic amines as affected by muscle types/skin and cooking in pan-roasted mackerel.
2002-03-25
Effect of conjugated linoleic acid on the formation of spontaneous and PhIP-induced mutation in the colon and cecum of rats.
2002-03-20
Effects of dairy products on heterocyclic aromatic amine-induced rat colon carcinogenesis.
2002-03
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.
2002-02
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.
2002-02
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.
2002-02
Human prostate epithelial cells metabolize chemicals of dietary origin to mutagens.
2002-01-25
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.
2002-01
Differential metabolism of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in rat and human hepatocytes.
2002-01
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
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.
2001-12-15
Clean-up procedures for the analysis of heterocyclic aromatic amines (aminoazaarenes) from heat-treated meat samples.
2001-12-14
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.
2001-12
Chemopreventive effects of ONO-8711, a selective prostaglandin E receptor EP(1) antagonist, on breast cancer development.
2001-12
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.
2001-11-15
Detection of PhIP (2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine) in the milk of healthy women.
2001-11
Biochemical effects of dietary intakes of different broccoli samples. I. Differential modulation of cytochrome P-450 activities in rat liver, kidney, and colon.
2001-10
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.
2001-09-20
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
Patents

Patents

20020006630
1

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
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 Mon Mar 31 18:48:55 GMT 2025
Edited
by admin
on Mon Mar 31 18:48:55 GMT 2025
Record UNII
909C6UN66T
Record Status Validated (UNII)
Record Version
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Name Type Language
PHIP
MI  
Preferred Name English
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
Code System Code Type Description
HSDB
7768
Created by admin on Mon Mar 31 18:48:55 GMT 2025 , Edited by admin on Mon Mar 31 18:48:55 GMT 2025
PRIMARY
CAS
105650-23-5
Created by admin on Mon Mar 31 18:48:55 GMT 2025 , Edited by admin on Mon Mar 31 18:48:55 GMT 2025
PRIMARY
PUBCHEM
1530
Created by admin on Mon Mar 31 18:48:55 GMT 2025 , Edited by admin on Mon Mar 31 18:48:55 GMT 2025
PRIMARY
WIKIPEDIA
2-Amino-1-methyl-6-phenylimidazo(4,5-b)pyridine
Created by admin on Mon Mar 31 18:48:55 GMT 2025 , Edited by admin on Mon Mar 31 18:48:55 GMT 2025
PRIMARY
CHEBI
76290
Created by admin on Mon Mar 31 18:48:55 GMT 2025 , Edited by admin on Mon Mar 31 18:48:55 GMT 2025
PRIMARY
MERCK INDEX
m8705
Created by admin on Mon Mar 31 18:48:55 GMT 2025 , Edited by admin on Mon Mar 31 18:48:55 GMT 2025
PRIMARY Merck Index
DRUG BANK
DB08398
Created by admin on Mon Mar 31 18:48:55 GMT 2025 , Edited by admin on Mon Mar 31 18:48:55 GMT 2025
PRIMARY
MESH
C049584
Created by admin on Mon Mar 31 18:48:55 GMT 2025 , Edited by admin on Mon Mar 31 18:48:55 GMT 2025
PRIMARY
EPA CompTox
DTXSID3037628
Created by admin on Mon Mar 31 18:48:55 GMT 2025 , Edited by admin on Mon Mar 31 18:48:55 GMT 2025
PRIMARY
NCI_THESAURUS
C29792
Created by admin on Mon Mar 31 18:48:55 GMT 2025 , Edited by admin on Mon Mar 31 18:48:55 GMT 2025
PRIMARY
FDA UNII
909C6UN66T
Created by admin on Mon Mar 31 18:48:55 GMT 2025 , Edited by admin on Mon Mar 31 18:48:55 GMT 2025
PRIMARY
Related Record Type Details
JAPANESE EEL, COOKED
PARENT -> CONSTITUENT ALWAYS PRESENT
Heterocyclic amine skin content in cooked food sample. 359?56 pg/g sample. Heterocyclic amine flesh content in cooked food sample. 214 pg/g sample.
CHUM SALMON, COOKED
PARENT -> CONSTITUENT ALWAYS PRESENT
Heterocyclic amine skin content in cooked food sample. 5928?802 pg/g sample. Heterocyclic amine flesh content in cooked food sample. 294 pg/g sample.
BEEF
PARENT -> CONSTITUENT ALWAYS PRESENT
Heterocyclic amine in well cooked meat sample. 634?75 pg/g sample. Heterocyclic amine in medium cooked meat sample. 537?105 pg/g sample.
PACIFIC SAURY, COOKED
PARENT -> CONSTITUENT ALWAYS PRESENT
Heterocyclic amine content in skin cooked food sample. 1611?196 pg/g sample. Heterocyclic amine flesh content in flesh cooked food sample. 333 pg/g sample.
JAPANESE PILCHARD, COOKED
PARENT -> CONSTITUENT ALWAYS PRESENT
Heterocyclic amine skin content in cooked food sample. 816?79 pg/g sample.
JAPANESE SCAD, COOKED
PARENT -> CONSTITUENT ALWAYS PRESENT
Heterocyclic amine skin content in cooked food sample. 2121?69 pg/g sample. Heterocyclic amine flesh content in cooked food sample. 160 pg/g sample.
PACIFIC CHUB MACKEREL, COOKED
PARENT -> CONSTITUENT ALWAYS PRESENT
Heterocyclic amine skin content in cooked food sample. 1595?218 pg/g sample. Heterocyclic amine flesh content in cooked food sample. 226 pg/g sample.
JAPANESE SCAD, COOKED
PARENT -> CONSTITUENT ALWAYS PRESENT
Semi-Dried(Aji-Hiraki) JAPANESE HORSE MACKEREL SKIN, COOKED Heterocyclic amine skin content in cooked food sample. 3682?331 pg/g sample. Heterocyclic amine skin content in cooked food sample. 524 pg/g sample.
CYTOCHROME P450 1A2
METABOLIC ENZYME -> SUBSTRATE
PORK, COOKED
PARENT -> CONSTITUENT ALWAYS PRESENT
Heterocyclic amine in cooked meat sample. 857?100 pg/g sample.
CHICKEN, COOKED
PARENT -> CONSTITUENT ALWAYS PRESENT
Heterocyclic amine in cooked meat sample 289?37 pg/g sample.
ATKA MACKEREL, COOKED
PARENT -> CONSTITUENT ALWAYS PRESENT
Heterocyclic amine skin content in cooked food sample. 5377?309 pg/g sample. Heterocyclic amine flesh content in cooked food sample. 658 pg/g sample.
Related Record Type Details
Structure of N2-Hydroxy-PhIP-N2-glucuronide
METABOLITE -> PARENT
MAJOR
Structure of N-hydroxy-PhIP sulfate ester
METABOLITE TOXIC -> PARENT
Putative mutagenic metabolite. Reacts with DNA.
Structure of N-hydroxy-PhIP acetyl ester
METABOLITE TOXIC -> PARENT
Mutagenic metabolite that reacts with DNA.
Structure of N-hydroxy-PhIP
METABOLITE -> PARENT
NIH
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