barbital

Barbital
Systematic (IUPAC) name
5,5-diethylpyrimidine-2,4,6(1H,3H,5H)-trione
Identifiers
CAS number	57-44-3
ATC code	N05CA04
PubChem	2294
DrugBank	DB01483
ChemSpider	2206
Chemical data
Formula	C8H12N2O3
Mol. mass	184.193 g/mol
SMILES	eMolecules & PubChem
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	Oral
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Barbital (marketed under the brand name Veronal), also called barbitone, was the first commercially marketed barbiturate. It was used as a sleeping aid (hypnotic) from 1903 until the mid-1950s. The chemical names for barbital are diethylmalonyl urea or diethylbarbituric acid. Veronal was prepared by condensing diethylmalonic ester with urea in the presence of sodium ethylate, or by adding ethyl iodide to the silver salt of malonylurea. The result was an odorless, slightly bitter, white crystalline powder.

Synthesis

Barbital was first synthesized in 1902 by German chemists Emil Fischer and Joseph von Mering. They published their discovery in 1903 and it was marketed in 1904 by the Bayer company as “Veronal”. A soluble salt of barbital was marketed by the Schering company as “Medinal.” It was dispensed for “insomnia induced by nervous excitability”. [1] It was provided in either capsules or cachets. The therapeutic dose was ten to fifteen grains (0.65-0.97 grams). 3.5 to 4.4 grams is the deadly dose but sleep has also been prolonged up to ten days with recovery. The Norwegian scientist Kristian Birkeland died in 1917 after taking 11 grams of veronal^[1].

Pharmacology

Veronal was considered to be a great improvement over the existing hypnotics. Its taste was slightly bitter, but an improvement over the strong, unpleasant taste of the commonly used bromides. It had few side effects. Its therapeutic dose was far below the toxic dose. However, prolonged usage resulted in tolerance to the drug, requiring higher doses to reach the desired effect. Fatal overdoses of this slow acting hypnotic were not uncommon.

References

• Fischer, Emil and Joseph von Mering, “Ueber eine neue Klasse von Schlafmitteln”, Therap Gegenw 44:97-101, 1903.
• "Veronal", in Finley, Ellingwood, M.D. The American Materia Medica, Therapeutics and Pharmacognosy", 1919. [2], accessed 07 Nov 2005.
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This article incorporates text from the Encyclopædia Britannica, Eleventh Edition, a publication now in the public domain.

Footnotes