Identification of 5‐Ethyl‐5‐(2‐methylbutyl)barbituric Acid as an Impurity of Manufacture in Amobarbital

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‐ethyi‐5‐(2‐methylbutyl)‐barbituric acid (1) by MS...

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Bibliographic Details
Published in:Journal of pharmaceutical sciences 1992-04, Vol.81 (4), p.362-364
Main Authors: Soine, William H., Graham, Ruth M., Soine, Phyllis J.
Format: Article
Language:English
Subjects:
Amobarbital - analysis
Amobarbital - chemistry
Amobarbital - isolation & purification
Amobarbital - toxicity
Analysis
Animals
Biological and medical sciences
Chemistry, Pharmaceutical - methods
Chromatography, High Pressure Liquid
Drug Contamination
General pharmacology
Magnetic Resonance Spectroscopy
Mass Spectrometry
Medical sciences
Pharmacology. Drug treatments
Rats
Spectrophotometry, Ultraviolet
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Summary: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‐ethyi‐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
ISSN:0022-3549
1520-6017
DOI:10.1002/jps.2600810415