112806-33-4

Basic information

• Product Name: amitriptyline N-glucuronide
• Synonyms: amitriptyline N-glucuronide
• CAS NO: 112806-33-4
• Molecular Formula: C26H31 N O6
• Molecular Weight: 0
• Mol File: 112806-33-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Methanol (Slightly), Water (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: amitriptyline N-glucuronide(CAS DataBase Reference)
• NIST Chemistry Reference: amitriptyline N-glucuronide(112806-33-4)
• EPA Substance Registry System: amitriptyline N-glucuronide(112806-33-4)

Safety Data

• Hazardous Substances Data: 112806-33-4(Hazardous Substances Data)

Usage

Uses

Amitriptyline N-β-D-Glucuronide is used in biological studies for biphasic kinetics of quaternary ammonium glucuronide formation from amitriptyline and diphenhydramine in human liver microsomes. Also, this compound is used in analytical studies to detect amitriptyline and diphenhydramine N-glucuronides in human urine using HPLC with and without hydrolysis.

InChI:InChI=1/C26H31NO6/c1-27(2,25-23(30)21(28)22(29)24(33-25)26(31)32)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-12,21-25,28-30H,7,13-15H2,1-2H3/t21-,22-,23+,24-,25+/m0/s1

Upstream product

• 1207167-94-9 CF₃O₃S^(1-)*C₃₉H₅₂NO₉⁽¹⁺⁾ 

Relevant articles and documents

A convenient new synthesis of quaternary ammonium glucuronides of drug molecules

N-Glucuronides, of various structural types, are frequently encountered as drug metabolites. Efficient chemical synthesis of these compounds, both as analytical standards and for toxicological investigation, is therefore an important goal. Earlier syntheses of N+- glucuronides of aliphatic tertiary amine drugs involved direct reaction of the drug molecule with a bromosugar, but yields were generally low and of poor reproducibility, with many by-products. In addition the final products were often of low stability, hindering effective isolation and purification. We now report that a stable, readily prepared glucuronic acid hemiacetal is a reliable precursor for metabolites of this type and give three pharmaceutically relevant examples. We report further on the stability of the final metabolites and the conditions required for their isolation and purification.