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
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)
| 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
| Title | Date | PubMed |
|---|---|---|
| Genetically modified Chinese hamster ovary cells for investigating sulfotransferase-mediated cytotoxicity and mutation by 2-amino-1-methyl-6- phenylimidazo[4,5-b]pyridine. | 2000 |
|
| More frequent beta-catenin gene mutations in adenomas than in aberrant crypt foci or adenocarcinomas in the large intestines of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP)-treated rats. | 2000 Aug |
|
| Characterization of peroxisome proliferator-activated receptor alpha in normal rat mammary gland and 2-amino-l-methyl-6-phenylimidazo[4, 5-b]pyridine-induced mammary gland tumors from rats fed high and low fat diets. | 2000 Dec 20 |
|
| The food-derived carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine activates S-phase checkpoint and apoptosis, and induces gene mutation in human lymphoblastoid TK6 cells. | 2000 Mar 1 |
|
| Delay of DNA-adduct repair and severe toxicity in xeroderma pigmentosum group A gene (XPA) deficient mice treated with 2-amino-1-methyl-6-phenyl-imidazo [4,5-b] pyridine (PhIP). | 2000 Mar 13 |
|
| Specificity of mutations induced by the food-associated heterocyclic amine 2-amino-1-methyl-6-phenylimidazo-[4,5-b]-pyridine in colon cancer cell lines defective in mismatch repair. | 2000 Sep 1 |
|
| 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 |
|
| Liquid chromatography-tandem mass spectrometry method of urine analysis for determining human variation in carcinogen metabolism. | 2001 Apr 20 |
|
| Functional characterization of nucleotide polymorphisms in the coding region of N-acetyltransferase 1. | 2001 Aug |
|
| Inhibition by green tea catechins of metabolic activation of procarcinogens by human cytochrome P450. | 2001 Aug 8 |
|
| 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 |
|
| Inhibitory effects of bitter melon (Momordica charantia Linn.) on bacterial mutagenesis and aberrant crypt focus formation in the rat colon. | 2001 Feb |
|
| Early detection of 2-amino-1-methyl-6-phenylimidazo (4,5-b)pyridine(PhIP)-induced mutations within the Apc gene of rat colon. | 2001 Feb |
|
| Oral administration of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) yields PhIP-DNA adducts but not tumors in male Syrian hamsters congenic at the N-acetyltransferase 2 (NAT2) locus. | 2001 Feb |
|
| Frequent c-Ha-ras gene mutations in rat mammary carcinomas induced by 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine. | 2001 Feb 26 |
|
| Carcinogen substrate specificity of human COX-1 and COX-2. | 2001 Jan |
|
| Protection against 2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine cytotoxicity and DNA adduct formation in human prostate by glutathione S-transferase P1. | 2001 Jan 1 |
|
| Effects of heterocyclic amines with mammary gland carcinogenic potential on estrogenic response of uterus in ovariectomized rats. | 2001 Jan 10 |
|
| Lack of UGT1 isoforms in Gunn rats changes metabolic ratio and facilitates excretion of the food-derived carcinogen 2-amino-1-methyl-6-phenylimidazo. | 2001 Jan 15 |
|
| Dietary intake of heterocyclic amines, meat-derived mutagenic activity, and risk of colorectal adenomas. | 2001 May |
|
| Curcumin modifies Apc(min) apoptosis resistance and inhibits 2-amino 1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) induced tumour formation in Apc(min) mice. | 2001 May |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Effect of cruciferous vegetable consumption on heterocyclic aromatic amine metabolism in man. | 2001 Sep |
|
| 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 |
|
| Cell transformation in vitro by food-derived heterocyclic amines Trp-P-1, Trp-P-2 and N(2)-OH-PhIP. | 2001 Sep 14 |
|
| Sex-specific induction of mutations by PhIP in the kidney of male and female rats and its modulation by conjugated linoleic acid. | 2002 |
|
| 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 |
|
| 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 |
|
| Effect of conjugated linoleic acid on the formation of spontaneous and PhIP-induced mutation in the colon and cecum of rats. | 2002 Mar 20 |
|
| 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 |
|
| 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 |
|
| 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
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 22:33:47 UTC 2022
by
admin
on
Fri Dec 16 22:33:47 UTC 2022
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| Record UNII |
909C6UN66T
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| Record Status |
Validated (UNII)
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| Record Version |
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2-Amino-1-methyl-6-phenylimidazo(4,5-b)pyridine
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M8705
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DB08398
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DTXSID3037628
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C29792
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909C6UN66T
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| Related Record | Type | Details | ||
|---|---|---|---|---|
|
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.
|
||
|
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.
|
||
|
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.
|
||
|
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.
|
||
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
Heterocyclic amine skin content in cooked food sample. 816?79 pg/g sample.
|
||
|
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.
|
||
|
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.
|
||
|
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.
|
||
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
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.
|
||
|
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.
|
