Basic information
- CAS
77-65-6- Standard SMILES
CCC(Br)(CC)C(=O)NC(N)=O- InChIKey
OPNPQXLQERQBBV-UHFFFAOYSA-N- Molecular formula
- C7H13BrN2O2
- Average molar mass
- 237.09 g/mol
- Monoisotopic mass
- 236.01604
Overview
Alpha-bromo-alpha-ethylbutyrylurea is an odorless tasteless white crystalline powder. Saturated solution in water neutral to litmus. (NTP, 1992)
Names & identifiers
- Preferred name
- Hoggar
- IUPAC
- 2-bromo-N-carbamoyl-2-ethylbutanamide
- English name
- (2-Bromo-2-ethylbutyryl)urea
- Molecular formula
- C7H13BrN2O2
- Molecular weight
- 237.09
Names & synonyms
CARBROMAL77-65-6AdalinHoggarBromadelCarbromalumButanamide, N-(aminocarbonyl)-2-bromo-2-ethyl-2-Bromo-2-ethylbutyrylureaDTXSID80202522-bromo-2-ethylbutyryureaNSC-491910Y299JY9V3
Show more names
NictalNYCTALURADALTILDINFydalinKartrylNenesin
DTXCID80252(2-bromo-2-ethylbutanoyl)ureaRefChem:123685N05CM04201-046-6BromadalDiacid2-bromo-N-carbamoyl-2-ethylbutanamide
Database identifiers
- CAS
77-65-6- PubChem CID
- 6488
- DTXSID
DTXSID8020252- ChEMBL
CHEMBL1697828- ChEBI
CHEBI:134961- UNII
- 0Y299JY9V3
- EC Number
- 201-046-6
- Nikkaji
- J4.210B
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 72.2 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 3
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 190
Experimental & physicochemical properties
DrugsDEA NFLIS-Drug Category -> Depressants and Tranquilizers
LogP1.54
OdorODORLESS
TasteTASTELESS
Density
1.544 at 77 °F (NTP, 1992) - Denser than water; will sink
1.544 @ 25 °C
Color/Form
WHITE, CRYSTALLINE POWDER
CRYSTALS
RHOMBIC CRYSTALS FROM DIL ALCOHOL
Solubility
less than 1 mg/mL at 72 °F (NTP, 1992)
1 G DISSOLVES IN ABOUT 3000 ML WATER, 18 ML ALCOHOL, 3 ML CHLOROFORM, 14 ML ETHER; VERY SOL IN BOILING ALCOHOL; DISSOLVES IN CONCN SULFURIC, NITRIC & HCL ACIDS; DISSOLVED BY SOLN OF ALKALI HYDROXIDES
SOL IN ACETONE & BENZENE
Human DrugsPharmaceuticals
Melting Point
244 °F (NTP, 1992)
116-119 °C
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (50%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P301+P317, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationButanamide, N-(aminocarbonyl)-2-bromo-2-ethyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationIMAP assessments - Butanamide, N-(aminocarbonyl)-2-bromo-2-ethyl-: Human health tier I assessment
Fire HazardsFlash point data for this compound are not available; however, it is probably combustible. (NTP, 1992)
Health Hazards
SYMPTOMS: Symptoms of exposure to this compound include mental confusion, ataxia, arreflexia, loss of pupillary response, cyanosis and coma. Other symptoms include severe mental depression, irritability, slurred speech and skin eruptions. Rashes may also occur.
Reactive GroupAmides and Imides
Special ReportsDHEW/NCI; Bioassay of Carbromal for Possible Carcinogenicity (1979) Technical Rpt Series No. 173 DHEW Pub No. (NIH) 79-1729
Reactivity ProfileThe neat material may be sensitive to prolonged exposure to air and light. This chemical is incompatible with acids and alkalis. (NTP, 1992)
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
Mechanism of ActionPARTIALLY DECOMP TO BROMIDE ION, BUT SEDATIVE ACTION IS PRESUMABLY DUE TO INTACT MOLECULE.
Metabolism/Metabolites
BIOTRANSFORMATION OF CARBROMAL...IN DOGS & RODENTS AFFORDED 2-BROMO-2-ETHYL-3-HYDROXYBUTYRYLUREA & 2-ETHYLBUTRYLUREA. HYDROXYLATION OF ACYL RESIDUE PREDOMINATES IN DOGS, & REDUCTIVE DEBROMINATION PREDOMINATES IN RATS, WHEREAS BOTH REACTIONS ARE IMPORTANT TO MICE. /LATTER/...FOUND IN BODY OF POISONED HUMAN SUBJECTS.
IN MAMMALIAN LIVER...CARBROMAL...IS TRANSFORMED... (OMEGA-1) OXIDATION, WHICH IS SPECIES DEPENDENT, OCCURS IN MICE, BUT NOT IN DOGS OR RATS, WHEREAS REDUCTIVE DEBROMINATION TAKES PLACE IN ALL 3 SPECIES.
...CARBROMAL...HAS BEEN FOUND TO UNDERGO RAPID BIOTRANSFORMATION TO CIS-2-ETHYLCROTONYLUREA IN RABBIT LIVER PREPN.
IT IS READILY OXIDIZED TO UREA IN BODY...
2-BROMO-2- ETHYL-4-HYDROXYBUTYRAMIDE & 2-BROMO-2-ETHYL-4-BUTYROLACTAM WERE ISOLATED FROM THE URINE OF MICE, RATS, & DOGS AFTER APPLICATION OF CARBROMAL. IDENTIFICATION WAS BY MASS, NMR, & IR SPECTROSCOPY.
Absorption, Distribution and Excretion
IT IS READILY OXIDIZED TO UREA IN BODY...
BIOTRANSFORMATION OF CARBROMAL...IN DOGS & RODENTS AFFORDED 2-BROMO-2-ETHYL-3-HYDROXYBUTYRYLUREA & 2-ETHYLBUTRYLUREA. HYDROXYLATION OF ACYL RESIDUE PREDOMINATES IN DOGS, & REDUCTIVE DEBROMINATION PREDOMINATES IN RATS, WHEREAS BOTH REACTIONS ARE IMPORTANT TO MICE. /LATTER/...FOUND IN BODY OF POISONED HUMAN SUBJECTS.
...DIFFERENT ANESTHETIC EFFECTS OBSERVED IN.../MICE, DOGS & RATS/ AFTER DOSE OF DRUG CAN BE ACCOUNTED FOR BY DIFFERENCES IN RATES OF METAB & CONSEQUENT DIFFERENCES IN PROPORTIONS OF RESULTING METABOLITES.
BROMINE CONCN IN URINE AFTER INGESTION OF CARBROMAL IS DESCRIBED.
PHARMACOKINETICS OF CARBROMAL IN THE RAT AND IN MAN.
Uses & manufacturing
UsesMEDICATION
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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