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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
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.

Contents

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.

Barbital Synthese.svg

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.

Popular Culture

The novel Valley of the Dolls by Jacqueline Susann references the slang term "dolls" or "barbie dolls" for a semi-fictional sedative. The term is possibly derived from the phonetic pronunciation of "barbital" which sounds very similar to "barbie doll".

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.
  • "Emma Zunz" by Jorge Luis Borges (short story)
  • The Murder of Roger Ackroyd by Agatha Christie (novel)
  • Lord Edgware Dies by Agatha Christie (novel)
  • Quartet by Jean Rhys (novel)
  • "Fräulein Else" by Arthur Schnitzler (novella)

This article incorporates text from the Encyclopædia Britannica, Eleventh Edition, a publication now in the public domain.

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