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    
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.
W H Soine; R M Graham; P J Soine
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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    
Department of Medicinal Chemistry, School of Pharmacy, Virginia Commonwealth University, Richmond 23298-0581.
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MeSH Terms
Amobarbital / analysis*,  chemistry*,  isolation & purification,  toxicity
Chemistry, Pharmaceutical / methods
Chromatography, High Pressure Liquid
Drug Contamination
Magnetic Resonance Spectroscopy
Mass Spectrometry
Spectrophotometry, Ultraviolet
Grant Support
Reg. No./Substance:
36082-56-1/5-ethyl-5-(2-methylbutyl)barbituric acid; 57-43-2/Amobarbital

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