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Merck
CN

SMB01383

PhIP

≥95% (HPLC)

Synonym(s):

2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine

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About This Item

Empirical Formula (Hill Notation):
C13H12N4
CAS Number:
105650-23-5
Molecular Weight:
224.26
UNSPSC Code:
12352100
NACRES:
NA.28
MDL number:
MFCD00210745

Key Documents

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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)

InChI key

UQVKZNNCIHJZLS-UHFFFAOYSA-N

SMILES string

NC1=NC2=NC=C(C3=CC=CC=C3)C=C2N1C

biological source

synthetic

assay

≥95% (HPLC)

form

solid

shipped in

2-8°C

storage temp.

2-8°C

Quality Level

200

General description

PhIP (2-Amino-1-methyl-6-phenylimidazo(4,5-b)pyridine) is a dietary genotoxic carcinogen formed in heat processed meat and fish via the Maillard reaction. PhIP is a primary metabolite activated by CYP1A2 and N-acetyltransferase 1 or sulfotransferase to DNA reactive metabolite.

Biochem/physiol Actions

Carcinogen developed in grilled meats. Induces breast and colon cancer in rats.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Carc. 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000239620
0000239620
0000230035
0000230035

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Iftikhar Ali Khan et al.
Meat science, 184, 108693-108693 (2021-11-15)
At this point in time, the evidence of a link between well-done meat intake and the incidence of cancer is stronger than it was 20 years ago. Several cohort and case-control studies have confirmed this evidence, and have shown a
Yueliang Zhao et al.
Journal of agricultural and food chemistry, 69(46), 13933-13941 (2021-11-11)
The effects of the deacetylation degree (DD) of chitosan on heterocyclic aromatic amine formation were investigated in chemical models and beef patties. The results in model systems showed that at lower addition levels (10 mg), chitosan with 85% DD showed
Robbert Ijsselsteijn et al.
Carcinogenesis, 43(2), 160-169 (2021-12-18)
The prevalent cancer predisposition Lynch syndrome (LS, OMIM #120435) is caused by an inherited heterozygous defect in any of the four core DNA mismatch repair (MMR) genes MSH2, MSH6, MLH1 or PMS2. MMR repairs errors by the replicative DNA polymerases
Shambhunath Choudhary et al.
Carcinogenesis, 33(4), 876-885 (2012-02-07)
More than 85% of breast cancers are sporadic and attributable to long-term exposure to environmental carcinogens, such as those in the diet, through a multistep disease process progressing from non-cancerous to premalignant and malignant stages. The chemical carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP)

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