Barbital

Structural formula
General
Non-proprietary name	Barbital
other names	5,5-diethylbarbituric acid ( IUPAC ) ; 5,5-diethyl- (1 H , 3 H , 5 H ) -pyrimidine-2,4,6-trione; Veronal;
Molecular formula	C 8 H 12 N 2 O 3
External identifiers / databases
EC number	200-331-2
ECHA InfoCard	100,000,301
PubChem	2294
DrugBank	DB01483
Wikidata	Q412409
Drug information
ATC code	N05 CA04
Drug class	sedative
properties
Molar mass	184.19 g mol −1
Physical state	firmly
Melting point	189-191 ° C
pK s value	8.14 (15 ° C)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: no P-phrases
Toxicological data	600 mg kg −1 ( LD 50 , rat , oral ) ; 450 mg kg −1 ( LD 50 , rat , sc ) ; 246 mg kg −1 ( LD 50 , rat , ip ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Barbital is a long-acting derivative of barbituric acid , which was previously used as a sleep aid . Because it can easily lead to death if improperly dosed - since it inhibits most metabolic processes - and there is also a risk of abuse, it is no longer used in this area of application.

history

Barbital was first produced in 1882 by Max Conrad and Max Guthzeit without further identification. Twenty years later, in 1902, it was first synthesized by Emil Fischer and his nephew Alfred Dilthey and characterized by Josef von Mering as a sleeping pill. Merck launched Barbital in tablet form under the brand name Veronal in 1903 as the first barbiturate. In combination with amidopyrin it was advertised as Veramon , u. a. also as a remedy for menstrual cramps , sold by the company Schering-Kahlbaum AG . Finished medicinal products containing barbital are no longer on the global market today.

Manufacturing

Barbital can be obtained preparatively from diethylmalonic acid diethyl ester and urea . The reaction takes place at 100 ° C under the influence of sodium ethoxide, the disodium salt of 5,5-diethylbarbituric acid precipitates. Barbital can also be produced directly from the diacid chloride of diethylmalonic acid and urea with the same yield. As early as 1904, Fischer used the term “veronal” for the alkali-free substance.

Use in chemistry

The diethylbarbituric acid monosodium salt is used as a buffer solution in electrophoresis ( veronal acetate buffer ), usually as a 0.02 to 0.05 molar solution . However, since procurement is severely restricted by the Narcotics Act , it is rarely used.

Barbital in literature, film and music

Glass bottle for veronal

Barbital was known as a preparation used for suicide and is often cited in the literature as a means of suicide under the previously common brand name Veronal until the 1960s , for example in Arthur Schnitzler's Miss Else or Vicki Baum's People in the Hotel .

In Agatha Christie's 1926 crime novel Alibi ( The Murder of Roger Ackroyd ) both the wealthy widow Mrs. Ferrars and later her blackmailer Dr. Sheppard killed by veronal, both with suicidal intent.

In the film Die Sünderin (1951) the leading actress actively euthanizes her boyfriend with veronal and then commits suicide in the same way. In the film Once Really Live (1952) a nurse replied to the question of what she would do if she had cancer : “There is enough veronal in this house, Doctor.” The repeated suicide attempts by one of the im is almost a running gag Background to the figure in Dany, called Monti , please write (1956) to describe: Since the fashion designer and womanizer Hannes Pratt ( Rudolf Prack ) keeps moving her, she keeps poisoning herself; the dose is always "skillfully measured". In Elevator to the Scaffold (1958), Veronique and Louis attempt suicide with Veronal.

On the album Fortunately in the future of the rapper Marteria , a song is dedicated to the sleeping pill veronal. The drug also appears in the song Lasky Jedne Plarovlasky (album Original Gasman Band , 1989) by the Munich band FSK .

In the twelfth episode ( atomic ghosts ) of the radio play series Larry Brent , the title hero is supposed to be killed with veronal, which is prevented by a blood wash. In Truman Capote's novella Breakfast at Tiffany's , Veronal is mentioned several times by the literary figure Holly Golightly.

In the novel Stalingrad by the author Theodor Plievier , Colonel Enders commits suicide with veronal in order to escape capture by the Red Army .

literature

Veronal . In: Encyclopædia Britannica . 11th edition. tape 27 : Tonalite - Vesuvius . London 1911, p. 1037 (English, full text [ Wikisource ]).
B. Molle, DH Kleist: Veronal . In: Archiv der Pharmazie , 242, 1904, pp. 401-406; doi: 10.1002 / ardp.19042420602 - solubilities and metabolism

Individual evidence

↑ ^a ^b ^c ^d ^e ^f data sheet 5,5-diethylbarbituric acid from Sigma-Aldrich , accessed on December 2, 2016 ( PDF ).
^ Entry on Barbital in the DrugBank of the University of Alberta , accessed December 5, 2016.
↑ M. Conrad, M. Guthzeit: About barbituric acid derivatives. In: Reports of the German Chemical Society , 15, 1882, pp. 2844–2850.
^ Alfred Dilthey (* August 22, 1877 in Rheydt, † July 22, 1915 in Poland / Russia) - genealogy.net - Emil Fischer: From my life . P. 197 ff .; Text archive - Internet Archive
↑ E. Fischer, J. von Mering: About a new class of sleeping pills. In: Therapy of the Present. Volume 44, 1903, pp. 97-101.
↑ E. Fischer, A. Dilthey: About C-dialkylbarbituric acids and about the ureid of dialkylacetic acids . In: Justus Liebigs Annalen der Chemie , 335, 1904, pp. 334–368. doi: 10.1002 / jlac.19043350303
↑ AW Frahm, HHJ Hager, F. v. Bruchhausen, M. Albinus, H. Hager: Hager's Handbook of Pharmaceutical Practice: Volume 4: Substances AK . Birkhäuser, 1999, ISBN 978-3-540-52688-9 , p. 373.
↑ Cf. for example Hans Killian: Behind us there is only the Lord God. Sub umbra dei. A surgeon remembers. Kindler, Munich 1957; here: Licensed edition as Herder paperback (= Herder library. Volume 279). Herder, Freiburg / Basel / Vienna 1975, ISBN 3-451-01779-2 , p. 29.

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f data sheet 5,5-diethylbarbituric acid from Sigma-Aldrich , accessed on December 2, 2016 ( PDF ).

[2] Entry on Barbital in the DrugBank of the University of Alberta , accessed December 5, 2016.

[3] M. Conrad, M. Guthzeit: About barbituric acid derivatives. In: Reports of the German Chemical Society , 15, 1882, pp. 2844–2850.

[4] Alfred Dilthey (* August 22, 1877 in Rheydt, † July 22, 1915 in Poland / Russia) - genealogy.net - Emil Fischer: From my life . P. 197 ff .; Text archive - Internet Archive

[5] E. Fischer, J. von Mering: About a new class of sleeping pills. In: Therapy of the Present. Volume 44, 1903, pp. 97-101.

[6] E. Fischer, A. Dilthey: About C-dialkylbarbituric acids and about the ureid of dialkylacetic acids . In: Justus Liebigs Annalen der Chemie , 335, 1904, pp. 334–368. doi: 10.1002 / jlac.19043350303

[7] AW Frahm, HHJ Hager, F. v. Bruchhausen, M. Albinus, H. Hager: Hager's Handbook of Pharmaceutical Practice: Volume 4: Substances AK . Birkhäuser, 1999, ISBN 978-3-540-52688-9 , p. 373.

[8] Cf. for example Hans Killian: Behind us there is only the Lord God. Sub umbra dei. A surgeon remembers. Kindler, Munich 1957; here: Licensed edition as Herder paperback (= Herder library. Volume 279). Herder, Freiburg / Basel / Vienna 1975, ISBN 3-451-01779-2 , p. 29.