Document Detail


Identification of 5-ethyl-5-(2-methylbutyl)barbituric acid as an impurity of manufacture in amobarbital.
MedLine Citation:
PMID:  1501074     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Amobarbital [5-ethyl-5-(3-methylbutyl)barbituric acid], USP, was found to contain an impurity that was not associated with hydrolysis and decomposition of the barbiturate ring. The impurity was isolated by semipreparative HPLC and was identified as 5-ethyl-5-(2-methylbutyl)barbituric acid (1) by MS (electron impact and chemical ionization) and 1H NMR. The substitution pattern on the alkyl side chain was verified by using the achiral NMR shift reagent tris(6,6,7,7,8,8,8-heptafluoro-2,2- dimethyl-3,5-octanedionato)europium(III). Older samples of amobarbital, USP, contained greater than 6% of 1, whereas recent samples of amobarbital, USP, contained less than 1% of 1. Because the pharmacological profiles of 1 and amobarbital in rodents are comparable, the impurity probably does not constitute a clinically significant problem for humans.
Authors:
W H Soine; R M Graham; P J Soine
Related Documents :
3939544 - Demonstration of 4-aminobutyric acid aminotransferase deficiency in lymphocytes and lym...
423204 - Coenzyme--substrate adducts as inhibitors of mouse liver 3,4-dihydroxyphenylalanine dec...
15184904 - Para-position derivatives of fungal anthelmintic cyclodepsipeptides engineered with str...
11844694 - Leishmanicidal activity of some aliphatic diamines and amino-alcohols.
3584094 - Glycolipids of the bovine pineal organ and retina.
22214994 - First prokaryotic biodiversity assessment using molecular techniques of an acidic river...
Publication Detail:
Type:  Comparative Study; Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Journal of pharmaceutical sciences     Volume:  81     ISSN:  0022-3549     ISO Abbreviation:  J Pharm Sci     Publication Date:  1992 Apr 
Date Detail:
Created Date:  1992-09-17     Completed Date:  1992-09-17     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  2985195R     Medline TA:  J Pharm Sci     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  362-4     Citation Subset:  IM    
Affiliation:
Department of Medicinal Chemistry, School of Pharmacy, Virginia Commonwealth University, Richmond 23298-0581.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:
Amobarbital / analysis*,  chemistry*,  isolation & purification,  toxicity
Animals
Chemistry, Pharmaceutical / methods
Chromatography, High Pressure Liquid
Drug Contamination
Magnetic Resonance Spectroscopy
Mass Spectrometry
Rats
Spectrophotometry, Ultraviolet
Grant Support
ID/Acronym/Agency:
GM 34507/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
36082-56-1/5-ethyl-5-(2-methylbutyl)barbituric acid; 57-43-2/Amobarbital

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


Previous Document:  Crystal structures of a new oral iron chelator, 1,2-dimethyl-3-hydroxy-4-pyridone, and its solvates ...
Next Document:  Nuclear magnetic resonance spectrometric investigations of calcium antagonist drugs. III: Conformati...