Bromisoval

Bromisoval

Names
IUPAC name (RS)-2-Bromo-N-carbamoyl-3-methylbutanamide
Identifiers
CAS Number	496-67-3 Y 27109-49-5 R Y
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:31304
ChemSpider	2353 Y 129594 R Y 643139 S Y
ECHA InfoCard	100.007.115
EC Number	207-825-7
KEGG	D01391
MeSH	Bromisovalum
PubChem CID	2447 146955 R 735997 S
UNII	469GW8R486 Y
InChI InChI=1S/C6H11BrN2O2/c1-3(2)4(7)5(10)9-6(8)11/h3-4H,1-2H3,(H3,8,9,10,11) Y Key: CMCCHHWTTBEZNM-UHFFFAOYSA-N Y
SMILES CC(C)C(Br)c(:[o]):[nH]:c(:[nH2]):[o] CC(C)C(Br)C(=O)NC(N)=O
Properties
Chemical formula	C6H11BrN2O2
Molar mass	223.07 g·mol−1
log P	1.057
Acidity (pKa)	10.536
Basicity (pKb)	3.461
Pharmacology
ATC code	N05CM03 (WHO)
Routes of administration	Oral
Related compounds
Related ureas	Carbromal
Related compounds	3-Ureidopropionic acid beta-Ureidoisobutyric acid Carbamoyl aspartic acid N-Acetylaspartic acid Aceglutamide N-Acetylglutamic acid Citrulline
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Bromisoval (INN), commonly known as bromovalerylurea, is a hypnotic and sedative of the bromoureide group discovered by Knoll in 1907 and patented in 1909. It is marketed over the counter in Asia under various trade names (such as Brovarin), usually in combination with non-steroidal anti-inflammatory drugs.

Chronic use of bromisoval has been associated with bromine poisoning.

Bromovisal can be prepared by bromination of isovaleric acid by the Hell-Volhard-Zelinsky reaction followed by reaction with urea.