Synonym
N2-OH-PhIP; N2 OH PhIP; N2OHPhIP; N-Hydroxy PhIP; N-OH PhIP;
IUPAC/Chemical Name
2-Hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine
InChi Key
DCVWQAGUQFBCTF-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H12N4O/c1-17-11-7-10(9-5-3-2-4-6-9)8-14-12(11)15-13(17)16-18/h2-8,18H,1H3,(H,14,15,16)
SMILES Code
CN1C(NO)=NC2=NC=C(C3=CC=CC=C3)C=C21
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
240.26
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Vlaming ML, Teunissen SF, van de Steeg E, van Esch A, Wagenaar E, Brunsveld L, de Greef TF, Rosing H, Schellens JH, Beijnen JH, Schinkel AH. Bcrp1;Mdr1a/b;Mrp2 combination knockout mice: altered disposition of the dietary carcinogen PhIP (2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine) and its genotoxic metabolites. Mol Pharmacol. 2014 Mar;85(3):520-30. doi: 10.1124/mol.113.088823. Epub 2013 Dec 13. PubMed PMID: 24334255.
2: Chen C, Ma X, Malfatti MA, Krausz KW, Kimura S, Felton JS, Idle JR, Gonzalez FJ. A comprehensive investigation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) metabolism in the mouse using a multivariate data analysis approach. Chem Res Toxicol. 2007 Mar;20(3):531-42. Epub 2007 Feb 6. PubMed PMID: 17279779; PubMed Central PMCID: PMC1850849.
3: Kulp KS, Knize MG, Fowler ND, Salmon CP, Felton JS. PhIP metabolites in human urine after consumption of well-cooked chicken. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Mar 25;802(1):143-53. PubMed PMID: 15036006.
4: Prabhu S, Lee MJ, Hu WY, Winnik B, Yang I, Buckley B, Hong JY. 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. Anal Biochem. 2001 Nov 15;298(2):306-13. PubMed PMID: 11700987.
5: Crofts FG, Sutter TR, Strickland PT. Metabolism of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine by human cytochrome P4501A1, P4501A2 and P4501B1. Carcinogenesis. 1998 Nov;19(11):1969-73. PubMed PMID: 9855011.
6: Crofts FG, Strickland PT, Hayes CL, Sutter TR. Metabolism of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) by human cytochrome P4501B1. Carcinogenesis. 1997 Sep;18(9):1793-8. PubMed PMID: 9328177.
7: Dragsted LO, Alexander J, Wallin H, Frandsen H, Vang O. Bioactivation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]-pyridine by liver microsomes from three different rat strains. Pharmacol Toxicol. 1993 Jun;72(6):388-93. PubMed PMID: 8361949.
