Bromisoval

Bromisoval (INN), commonly known as bromovalerylurea, is a hypnotic and sedative of the bromoureide group discovered by Knoll in 1907 and patented in 1909.^[1] It is marketed over the counter in Asia under various trade names (such as Brovarin^[2]), usually in combination with nonsteroidal anti-inflammatory drugs.

Quick facts Names, Identifiers ...

Bromisoval

Names
IUPAC name (RS)-2-Bromo-N-carbamoyl-3-methylbutanamide[citation needed]
Identifiers
CAS Number	496-67-3 Y 27109-49-5 R Y 27109-48-4 S Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:31304
ChEMBL	ChEMBL1515611 Y
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 3DY4YGA2PX R Y GTJ4Y0JW4D S Y
CompTox Dashboard (EPA)	DTXSID2040656
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)NC(N)=O
Properties
Chemical formula	C6H11BrN2O2
Molar mass	223.070 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

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Chronic use of bromisoval has been associated with bromine poisoning.^[3][4][5][6]

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