18125-49-0

Basic information

• Product Name: 3-hydroxymethylantipyrine
• Synonyms: 3-hydroxymethylantipyrine;1-Methyl-2-phenyl-5-(hydroxymethyl)-4-pyrazoline-3-one;2-Methyl-3-(hydroxymethyl)-1-phenyl-3-pyrazolin-5-one;3H-Pyrazol-3-one, 1,2-dihydro-5-(hydroxyMethyl)-1-Methyl-2-phenyl-
• CAS NO: 18125-49-0
• Molecular Formula: C₁₁H₁₂N₂O₂
• Molecular Weight: 204.23
• Mol File: 18125-49-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 351.2°Cat760mmHg
• Flash Point: 166.2°C
• Appearance: /
• Density: 1.265g/cm³
• Vapor Pressure: 1.55E-05mmHg at 25°C
• Refractive Index: 1.611
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly, Heated, Sonicated), Methanol (Slightly, Sonicated)
• CAS DataBase Reference: 3-hydroxymethylantipyrine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxymethylantipyrine(18125-49-0)
• EPA Substance Registry System: 3-hydroxymethylantipyrine(18125-49-0)

Safety Data

• Hazardous Substances Data: 18125-49-0(Hazardous Substances Data)

Usage

Description

3-Hydroxymethylantipyrine is a metabolite of Antipyrine, a non-steroidal anti-inflammatory drug (NSAID) that is extensively used as a probe for human oxidative drug metabolism. It is formed through the action of various hepatic cytochrome P450 enzymes on Antipyrine.

Uses

Used in Pharmaceutical Research:
3-Hydroxymethylantipyrine is used as a biomarker for assessing the activity of hepatic cytochrome P450 enzymes, which are crucial in the metabolism of numerous drugs and xenobiotics. The measurement of this metabolite can help in understanding the metabolic profile of individuals and guide personalized drug therapy.
Used in Drug Metabolism Studies:
3-Hydroxymethylantipyrine is used as a research tool for studying the metabolism of Antipyrine and other NSAIDs. It aids in evaluating the efficiency and effectiveness of drug metabolism pathways, which is vital for drug development and optimization.
Used in Clinical Diagnostics:
3-Hydroxymethylantipyrine is used as a diagnostic indicator in clinical settings to monitor liver function and the status of cytochrome P450 enzyme activity. Abnormal levels of this metabolite may suggest impaired liver function or altered drug metabolism, prompting further investigation and appropriate medical intervention.

InChI:InChI=1/C11H12N2O2/c1-12-10(8-14)7-11(15)13(12)9-5-3-2-4-6-9/h2-7,14H,8H2,1H3

Upstream product

• 81122-69-2 3-hydroxymethyl-4-bromoantipyrine 
• 60-80-0 antipyrine 
• 5767-66-8 4-bromo-5-(bromomethyl)-1-methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one 

Downstream Products

• 33328-68-6 3-formyl-2-methyl-1-phenylpyrazol-5-one 
• 100135-42-0 4,5-bis-hydroxymethyl-1-methyl-2-phenyl-1,2-dihydro-pyrazol-3-one 
• 117000-86-9 1-methyl-2-phenyl-1,2-dihydro-pyrazolo[3,4-d]pyridazin-3-one 
• 104396-34-1 2-methyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazole-3,4-dicarbaldehyde 

Relevant articles and documents

An improved synthesis of 3-hydroxymethylantipyrine using antipyrine as starting material

A partly new synthesis of 3-hydroxymethylantipyrine, an important metabolite of antipyrine in man and therefore frequently used as a reference substance, is described. The use of tri-n-butyltin hydride to reduce the vinyl bromide system in 3-hydroxymethyl