CAS 496-67-3|Bromisoval

Introduction：Basic information about CAS 496-67-3|Bromisoval, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Bromisoval BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Customs
7. Synonyms

Common Name	Bromisoval
CAS Number	496-67-3	Molecular Weight	223.06800
Density	1.504g/cm3	Boiling Point	/
Molecular Formula	C₆H₁₁BrN₂O₂	Melting Point	152 °C
MSDS	/	Flash Point	/

Names

Name	2-bromo-N-carbamoyl-3-methylbutanamide
Synonym	More Synonyms

Bromisoval BiologicalActivity

Description	Bromisoval has anti-inflammatory effects and has been used as an old sedative and hypnotic.
Related Catalog	Signaling Pathways >>Others >>OthersResearch Areas >>Inflammation/ImmunologyResearch Areas >>Neurological Disease
In Vitro	Bromisoval (BU) suppresses nitric oxide (NO) releasing and proinflammatory cytokine expression in lipopolysaccharide (LPS)-treat BV2 cells, a murine microglial cell line. Bromisoval suppresses LPS-inducing phosphorylation of signal transducer and activator of transcription 1 (STAT1) and expression of interferon regulatory factor 1 (IRF1). The Janus kinase 1 (JAK1) inhibitor filgotinib suppresses the NO release much more weakly than that of Bromisoval, although filgotinib almost completely prevents LPS-inducing STAT1 phosphorylation. Knockdown of JAK1, STAT1, or IRF1 does not affect the suppressive effects of Bromisoval on LPS-inducing NO. A combination of Bromisoval and filgotinib synergistically suppress the NO releasing. The mitochondrial complex I inhibitor rotenone, which does not prevent STAT1 phosphorylation or IRF1 expression, suppresses proinflammatory mediator expression less significantly than Bromisoval. Bromisoval and rotenone reduce intracellular ATP (iATP) levels to a similar extent. A combination of rotenone and filgotinib suppress NO release in LPS-treated BV2 cells as strongly as Bromisoval[1].
In Vivo	Bromisoval (Bromvaletone) and carbromal are the most potent central depressants within each series. Depressant activities (ISD50 values) and acute toxicities (LD50 values) in male mice after intraperitoneal injection of Bromisoval are 0.35 (0.30-0.39) and 3.25 (2.89-3.62) mmol/kg, respectively[2].
Kinase Assay	Conditioning media are obtained from BV2 cell cultures that have been incubated for 24 h in E2 medium containing 1 μg/ml LPS, with or without Bromisoval (BU) (1-100 μg/mL) or other agents, and subjected to NO determination. To normalize the releasing NO level by the cellular protein contents, cells are solubilized with RIPA buffer (50 mM Tris-HCl, pH 8.0, 150 mM sodium chloride, 0.5% w/v sodium deoxycholate, 0.1% w/v sodium dodecyl sulfate, 1.0% w/v NP-40 substitute) and the protein contents are determined by BCA protein assay reagents[1].
Cell Assay	Murine microglial cell line BV2 is used. BV2 cells are maintained in medium supplemented with 10% fetal bovine serum. BV2 cells are seeded onto wells in 4-well culture plates and incubated with LPS for 30 min to 24 h. When the effects of Bromisoval (BU) or other agents are investigated, BV2 cells are incubated with the appropriate agent (e.g. Bromisoval) for 30 min before the addition of LPS[1].
Animal Admin	Suspensions of the compounds (including Bromisoval ) in aqueous 0.5% carboxymethyl cellulose are administered intraperitoneally to adult male albino mice weighing 25-35 g. All tests are performed on groups of ten mice[2].
References	[1]. Kawasaki S, et al. Effects of hypnotic bromovalerylurea on microglial BV2 cells. J Pharmacol Sci. 2017 Jun;134(2):116-123. [2]. Mrongovius RI, et al. Comparison of the bromureide sedative-hypnotic drugs, bromvaletone (bromisoval) and carbromal, and their chloro analogues in mice. Clin Exp Pharmacol Physiol. 1976 Sep-Oct;3(5):443-7.

Chemical & Physical Properties

Density	1.504g/cm3
Melting Point	152 °C
Molecular Formula	C₆H₁₁BrN₂O₂
Molecular Weight	223.06800
Exact Mass	222.00000
PSA	72.19000
LogP	1.69200
Index of Refraction	1.514
InChIKey	CMCCHHWTTBEZNM-UHFFFAOYSA-N
SMILES	CC(C)C(Br)C(=O)NC(N)=O

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YS3150000

CHEMICAL NAME :: Urea, (2-bromo-3-methylbutyryl)-

CAS REGISTRY NUMBER :: 496-67-3

BEILSTEIN REFERENCE NO. :: 1773255

LAST UPDATED :: 199806

DATA ITEMS CITED :: 10

MOLECULAR FORMULA :: C6-H11-Br-N2-O2

MOLECULAR WEIGHT :: 223.10

WISWESSER LINE NOTATION :: ZVMVYEY1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 400 mg/kg

TOXIC EFFECTS :: Behavioral - coma Gastrointestinal - nausea or vomiting

REFERENCE :: BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 1,1238,1955

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human

DOSE/DURATION :: 57 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TOIZAG Toho Igakkai Zasshi. Journal of Medical Society of Toho University. (Toho Daigaku Igakkai, 21-16, Omori-nishi, 5-chome, Ota-ku, Tokyo 143, Japan) V.1- 1954- Volume(issue)/page/year: 7,513,1960

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity)

REFERENCE :: FEPRA7 Federation Proceedings, Federation of American Societies for Experimental Biology. (Bethesda, MD) V.1-46, 1942-87. Volume(issue)/page/year: 7,262,1948

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1340 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,1213,1995

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 660 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,1213,1995

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 450 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,738,1982

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1289,1935

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Rectal

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 1400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TOIZAG Toho Igakkai Zasshi. Journal of Medical Society of Toho University. (Toho Daigaku Igakkai, 21-16, Omori-nishi, 5-chome, Ota-ku, Tokyo 143, Japan) V.1- 1954- Volume(issue)/page/year: 7,513,1960

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Amphibian - frog

DOSE/DURATION :: 900 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1289,1935

Safety Information

Safety Phrases	S24/25
RTECS	YS3150000
HS Code	2924210090

Customs

HS Code	2924210090
Summary	2924210090 other ureines and their derivatives; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

Synonyms

Alural

EINECS 207-825-7

Bromaral

Bromural

Alluval

Bromoxil

1-(2-Bromoisovaleryl)urea

Abroval

Bromisoval

bromisovalum

Bromovalerylurea

B.V.U.

Bromoval

Bromyl

MFCD00047873

2-Bromo-3-methylbutyrylurea

bromvalerylurea

Recommended......