Aprobarbital

Title: Aprobarbital
CAS Registry Number: 77-02-1
CAS Name: 5-(1-Methylethyl)-5-(2-propenyl)-2,4,6(1H,3H,5H)-pyrimidinetrione
Additional Names: 5-allyl-5-isopropylbarbituric acid; allypropymal
Trademarks: Alurate (Roche)
Molecular Formula: C10H14N2O3
Molecular Weight: 210.23
Percent Composition: C 57.13%, H 6.71%, N 13.33%, O 22.83%
Literature References: Prepn: US 1444802 (1923). Toxicity data: H. H. Frey, Arzneim.-Forsch. 12, 389 (1962).
Properties: Slightly bitter crystals, mp 140-141.5°. Almost insoluble in water, petr ether, aliphatic hydrocarbons. Sol in alcohol, chloroform, ether, acetone, benzene, glacial acetic acid, also in solns of fixed alkali hydroxides. A satd aq soln is acid to litmus. LD50 i.p. in mice: 200 mg/kg (Frey).
Melting point: mp 140-141.5°
Toxicity data: LD50 i.p. in mice: 200 mg/kg (Frey)
Derivative Type: Sodium salt
CAS Registry Number: 125-88-2
Additional Names: Aprobarbital sodium; sodium 5-allyl-5-isopropylbarbiturate
Molecular Formula: C10H13N2NaO3
Molecular Weight: 232.21
Percent Composition: C 51.72%, H 5.64%, N 12.06%, Na 9.90%, O 20.67%
Properties: Hygroscopic powder; slightly bitter taste. Very soluble in water; slightly sol in alc. Practically insol in ether. Aq solns are alkaline to litmus.
NOTE: This is a controlled substance (depressant): 21 CFR, 1308.13.
Therap-Cat: Sedative, hypnotic.
Keywords: Sedative/Hypnotic; Barbituric Acid Derivatives.
Apronalide Aprotinin Aptiganel Apyrase Aquaporins

Aprobarbital
Aprobarbital Structural Formulae.svg
Aprobarbital ball-and-stick animation.gif
Systematic (IUPAC) name
5-propan-2-yl-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
Clinical data
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Identifiers
CAS number 77-02-1
ATC code N05CA05
PubChem CID 6464
DrugBank DB01352
ChemSpider 6221 YesY
UNII Q0YKG9L6RF YesY
KEGG D00698 YesY
ChEBI CHEBI:2791 YesY
ChEMBL CHEMBL7863 YesY
Synonyms aprobarbital, Oramon, allylpropymal, Alurate, 5-isopropyl- 5-allylbarbituric acid
Chemical data
Formula C10H14N2O3 
Mol. mass 210.23 g/mol
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Aprobarbital (as known in the United States, or aprobarbitone (as known elsewhere), sold as Oramon, Somnifaine, and Allonal, is a barbiturate derivative invented in the 1920s by Ernst Preiswerk. It has sedative, hypnotic and anticonvulsant properties, and was used primarily for the treatment of insomnia.[1] Aprobarbital was never as widely used as more common barbiturate derivatives such as phenobarbital and is now rarely prescribed as it has been replaced by newer drugs with a better safety margin.