Barbital
Clinical data | |
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Trade names | Veronal, Medinal |
AHFS/Drugs.com | International Drug Names |
MedlinePlus | a682221 |
Routes of administration | Oral |
ATC code | |
Legal status | |
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Pharmacokinetic data | |
Elimination half-life | 30.3 (± 3.2) hours |
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Barbital (or barbitone), marketed under the brand names Veronal for the pure acid and Medinal for the sodium salt, was the first commercially available 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; hence, the sodium salt (known as medinal, a genericised trademark in the United Kingdom) is known also as sodium diethylbarbiturate.
Synthesis
Barbital, then called "Veronal", was first synthesized in 1902 by German chemists
Its introduction followed the investigations of Fischer and von Mering on the pharmacological properties of certain open and closed acylureas (then called ureides). Led by the impression that hypnotic action appears to be largely dependent on the presence of ethyl groups, they prepared diethylacetyl urea, diethylmalonyl urea (i.e., Barbital itself), and dipropylmalonyl urea. All three were found to be hypnotics: the first was about equal in power to the already-known sulphonal (now sulfonmethane), whilst the third was four times as powerful, but its use was attended by prolonged after-effects. Veronal was found to be midway.[3]
Barbital can also be synthesized in a
Marketing
Barbital was marketed in 1904 by the
Pharmacology
Barbital was considered to be a great improvement over the existing hypnotics. Its taste was slightly bitter, but better than the strong, unpleasant taste of the commonly used bromides. It had few side effects, and 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. "I'm literally saturated with it", the Russian tsarina Alexandra Feodorovna confessed to a friend.[5] Fatal overdoses of this slow-acting hypnotic were common. Pioneering aviator Arthur Whitten Brown (of "transatlantic flight of Alcock and Brown" fame) died of an accidental overdose.
A photoswitchable derivative of barbital based on a donor-acceptor Stenhouse adduct (DASA) has been developed for research purposes (photopharmacology). DASA-barbital shows neuronal activity via GABAA receptors and reversible photoisomerization in water using cyclodextrin.[6]
pH buffer
Solutions of sodium barbital have also been used as pH buffers for biological research, e.g., in immunoelectrophoresis or in fixative solutions.[7][8] As barbital is a controlled substance, barbital-based buffers have largely been replaced by other substances.[9]
Suicide
In fiction
In the D. H. Lawrence story, The Lovely Lady, the titular character dies from a self-administered overdose.[14]
Barbital, under the name of Veronal, has been used as a plot device in the author Agatha Christie's murder mysteries.[15]
Barbital was also used as a plot device in the CBS television legal drama, Perry Mason, in the episode, The Case of the Missing Element (1963).[16]
References
- ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
- Fischer E, von Mering J (1903). "Ueber eine neue Klasse von Schlafmitteln" [About a new class of sleeping pills]. Therapie der Gegenwart (in German). 44: 97–101.
- ^ a b public domain: Chisholm, Hugh, ed. (1911). "Veronal". Encyclopædia Britannica. Vol. 27 (11th ed.). Cambridge University Press. p. 1037. One or more of the preceding sentences incorporates text from a publication now in the
- ^ Finley E (1919). "Veronal". The American Materia Medica, Therapeutics and Pharmacognosy. p. 115. Retrieved 25 July 2015.
- ^ Dehn L (1922). The Real Tsaritsa. Boston: Little Brown. p. 138.
- S2CID 251623598.
- ^ Kuhlmann WD (10 September 2006). "Buffer Solutions" (PDF). Archived from the original (PDF) on 9 November 2016. Retrieved 28 July 2014.
- ^ Ruzin SE (1999). Plant Microtechnique and Microscopy. Oxford University Press. Archived from the original on 3 June 2019. Retrieved 28 July 2014.
- PMID 568042.
- ^ Le Matin (in French), 1942-07-06, retrieved 2022-06-04
- ^ I Will Bear Witness by Victor Klemperer (Author), Martin Chalmers (Translator) 1998
- ISBN 9780813121017.
- ^ "Im Interview: Judith Kerr - Wir waren eine Insel - Kultur - sueddeutsche.de". 2008-06-10. Archived from the original on 2008-06-10. Retrieved 2021-07-08.
- ISBN 978-0-86307-694-7.
- ^ "A quote from The Murder of Roger Ackroyd". www.goodreads.com. Retrieved 2021-10-22.
- ^ "The Case of the Missing Element (1963)". www.imdb.com. Retrieved 2024-03-05.
Further reading
- Dombrowski SM, Krishnan R, Witte M, Maitra S, Diesing C, Waters LC, Ganguly R (October 1998). "Constitutive and barbital-induced expression of the Cyp6a2 allele of a high producer strain of CYP6A2 in the genetic background of a low producer strain". Gene. 221 (1): 69–77. PMID 9852951.