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

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	MOL RATIO 1 MOL RATIO (average)

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

PubMed

Show entries

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
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	11774364
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
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

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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
Record UNII	909C6UN66T
Record Status	`Validated (UNII)`
Record Version

Show entries

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

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Code System

Code

Type

Description

HSDB

7768

PRIMARY

CAS

105650-23-5

PRIMARY

PUBCHEM

1530

PRIMARY

WIKIPEDIA

2-Amino-1-methyl-6-phenylimidazo(4,5-b)pyridine

PRIMARY

CHEBI

76290

PRIMARY

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