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Secobarbital
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C12H18N2O3 238.28

2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(1-methylbutyl)-5- (2-propenyl)-.
5-Allyl-5-(1-methylbutyl)barbituric acid [76-73-3].
» Secobarbital contains not less than 97.5 percent and not more than 100.5 percent of C12H18N2O3, calculated on the dried basis.
Packaging and storage— Preserve in tight containers.
Identification, Infrared Absorption 197M.
Loss on drying 731 Dry it over silica gel for 18 hours: it loses not more than 1.0% of its weight.
Residue on ignition 281: not more than 0.1%.
Organic volatile impurities, Method V 467: meets the requirements.
Solvent— Use dimethyl sulfoxide.
Isomer content— Dissolve about 300 ± 5 mg in 5 mL of sodium hydroxide solution (1 in 100), add a solution of 300 ± 5 mg of p-nitrobenzyl bromide in 10 mL of alcohol, reflux for 30 minutes, cool, collect the precipitate on a small filter, and wash with water: the precipitate, recrystallized from 25 mL of alcohol and dried at 105 for 30 minutes, melts between 156 and 161.
Residual solvents 467: meets the requirements.
(Official January 1, 2007)
Assay— Add about 450 mg of Secobarbital, accurately weighed, to 60 mL of dimethylformamide in a 125-mL conical flask. Add 4 drops of thymol blue TS, and titrate with 0.1 N sodium methoxide VS, using a magnetic stirrer and taking precautions against the absorption of atmospheric carbon dioxide. Perform a blank determination, and make any necessary correction. Each mL of 0.1 N sodium methoxide is equivalent to 23.83 mg of C12H18N2O3.
Auxiliary Information— Staff Liaison : Ravi Ravichandran, Ph.D., Senior Scientist
Expert Committee : (MDPP05) Monograph Development-Psychiatrics and Psychoactives
USP29–NF24 Page 1952
Phone Number : 1-301-816-8330