Bromoisoval

Structural formula
	1: 1 mixture of ( R ) -form (top) and ( S ) -form (bottom)
General
Non-proprietary name	Bromoisoval
other names	α-bromoisovalerianylurea; ( RS ) - (2-Bromo-3-methylbutyryl) urea; ( RS ) -2-bromo- N -carbamoyl- ; 3-methylbutanamide ( IUPAC ) ;
Molecular formula	C 6 H 11 BrN 2 O 2
External identifiers / databases
EC number	207-825-7
ECHA InfoCard	100.007.115
PubChem	2447
Wikidata	Q420899
Drug information
ATC code	N05 CM03
Drug class	Sedative , hypnotic
properties
Molar mass	223.08 g mol −1
Physical state	firmly
Melting point	147-149 ° 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: ?
Toxicological data	1340 mg kg −1 ( LD 50 , mouse , oral ) ; 660 mg kg −1 ( LD 50 , mouse , ip ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Bromisoval is a drug that has been used as a sedative and hypnotic . It was patented by Knoll in 1906 as Bromural ^® (out of trade).

chemistry

Chemically, it is, this is a brominated urea - derivative (Bromacylureid) connected to the Carbromal is used. In addition, the bromoacylureides are structurally close to barbituric acid . Bromisoval contains a stereocenter, hence there are two stereoisomers, ( R ) -Bromisoval and ( S ) -Bromisoval. The 1: 1 mixture of ( R ) -Bromisoval and ( S ) -Bromisoval is ( RS ) -Bromisoval, a racemate .

effect

Bromacylureides are less hypnotically effective than barbiturates . In the biotransformation of these agents are bromide - ion free, an elimination half-life comprise of 12 days. This leads to an accumulation with prolonged use .

unwanted effects

If taken for a long time, Bromisoval can lead to chronic bromine poisoning (so-called bromism ) - see Potassium bromide: Usage . Symptoms of an overdose are similar to those of barbiturates , but the mortality rate is very high (4–6%) because of the risk of developing a shock lung . There is also a risk of becoming addicted .

Individual evidence

↑ ^a ^b J. Falbe, M. Regitz (Ed.): Römpp Lexikon Chemie . 10th edition, Thieme, Stuttgart a. New York, 1996-1999. P. 524.
↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of Bromisoval in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), retrieved on December 28, 2019, is reproduced from a self-classification by the distributor .
↑ ^a ^b Entry on Bromisoval in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on December 28, 2019.
↑ ^a ^b H. J. Roth, H. Fenner: Medicines . Thieme, Stuttgart a. New York, 1988. p. 272.
↑ HPT Ammon (Ed.): Hunnius Pharmaceutical Dictionary . 9th edition, Walter de Gruyter, Berlin a. New York, 2004. p. 258.

[Römpp-1] J. Falbe, M. Regitz (Ed.): Römpp Lexikon Chemie . 10th edition, Thieme, Stuttgart a. New York, 1996-1999. P. 524.

[2] Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of Bromisoval in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), retrieved on December 28, 2019, is reproduced from a self-classification by the distributor .

[ChemIDplus-3] Entry on Bromisoval in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on December 28, 2019.

[Roth/Fenner-4] H. J. Roth, H. Fenner: Medicines . Thieme, Stuttgart a. New York, 1988. p. 272.

[5] HPT Ammon (Ed.): Hunnius Pharmaceutical Dictionary . 9th edition, Walter de Gruyter, Berlin a. New York, 2004. p. 258.