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PhIP

Names

[ CAS No. ]:
105650-23-5

[ Name ]:
PhIP

[Synonym ]:
4,5-b> 1-methyl-6-phenylimidazo[4,5-b]pyridin-2-amine
2-amino-1-methyl-6-phenylimidazo<4,5-f>pyridine
PIQ
MFCD00210745

Biological Activity

[Description]:

PhIP is the most abundant of generation of heterocyclic amines (HCA), resulted in the cooking of meat[1][2]. DNA damaging and mutagenic activities. PhIP also has oestrogenic activity that could contribute to its tissue specific carcinogenicity[2].

[Related Catalog]:

Research Areas >> Cancer
Signaling Pathways >> Others >> Others

[In Vitro]

PhIP causes widespread and largely over-lapping effects on miRNA expression. PhIP induces widespread effects via activation of oestrogen receptor alpha (ERα). Deregulation of miRNA by PhIP could potentially be an important non-DNA-damaging carcinogenic mechanism in breast cancer[2].

[In Vivo]

In hCYP1A-mice, PhIP induces inflammation, epithelial cell damage, and prostatic intraepithelial neoplasia in the dorsolateral prostate lobe compared to the ventral lobe. PhIP forms DNA adducts in the prostate, PhIP also induces oxidative stress, atrophy of the acini, and inflammation of the prostate of rodents[1].

[References]

[1]. Bellamri M, et al. Metabolic Activation of the Cooked Meat Carcinogen 2-Amino-1-Methyl-6-Phenylimidazo[4,5-b]Pyridine in Human Prostate. Toxicol Sci. 2018 Jun 1;163(2):543-556.

[2]. Papaioannou MD, et ak. The cooked meat-derived mammary carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) elicits estrogenic-like microRNA responses in breast cancer cells. Toxicol Lett. 2014 Aug 17;229(1):9-16.

Chemical & Physical Properties

[ Density]:
1.3 g/cm3

[ Boiling Point ]:
468.9ºC at 760 mmHg

[ Melting Point ]:
300ºC

[ Molecular Formula ]:
C13H12N4

[ Molecular Weight ]:
224.26100

[ Flash Point ]:
237.4ºC

[ Exact Mass ]:
224.10600

[ PSA ]:
56.73000

[ LogP ]:
2.79870

[ Vapour Pressure ]:
5.74E-09mmHg at 25°C

[ Index of Refraction ]:
1.699

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
NJ5199900
CHEMICAL NAME :
Imidazo(4,5-b)pyridine, 2-amino-1-methyl-6-phenyl-
CAS REGISTRY NUMBER :
105650-23-5
LAST UPDATED :
199712
DATA ITEMS CITED :
31
MOLECULAR FORMULA :
C13-H12-N4
MOLECULAR WEIGHT :
224.29
WISWESSER LINE NOTATION :
T56 BN DN FNJ B1 CZ HR

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
8736 mg/kg/52W-C
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
37056 mg/kg/83W-C
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Gastrointestinal - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
4200 mg/kg/44W-I
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Gastrointestinal - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
449 mg/kg/8W-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Skin and Appendages - tumors
TYPE OF TEST :
DNA adduct
TYPE OF TEST :
DNA adduct
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
Cytogenetic analysis
TYPE OF TEST :
Sister chromatid exchange
TYPE OF TEST :
Sister chromatid exchange
TYPE OF TEST :
Mutation in mammalian somatic cells

MUTATION DATA

TYPE OF TEST :
Mutation in mammalian somatic cells
TEST SYSTEM :
Rodent - hamster Lung
DOSE/DURATION :
10 umol/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 325,125,1994 *** REVIEWS *** IARC Cancer Review:Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 56,229,1993 IARC Cancer Review:Human Inadequate EvidenceE IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 56,229,1993 IARC Cancer Review:Group 2B IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 56,229,1993

Safety Information

[ Hazard Codes ]:
T: Toxic;

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Related Compounds