Carbromal

Title: Carbromal
CAS Registry Number: 77-65-6
CAS Name: N-(Aminocarbonyl)-2-bromo-2-ethylbutanamide
Additional Names: (a-bromo-a-ethylbutyryl)urea; (a-bromo-a-ethylbutyryl)carbamide; bromodiethylacetylurea; bromodiethylacetylcarbamide
Trademarks: Tildin; Adalin (Bayer); Planadalin; Diacid (Daro); Addisomnol (Synochem); Bromadal; Uradal; Nyctal
Molecular Formula: C7H13BrN2O2
Molecular Weight: 237.09
Percent Composition: C 35.46%, H 5.53%, Br 33.70%, N 11.82%, O 13.50%
Line Formula: (C2H5)2CBrCONHCONH2
Literature References: Prepd by heating urea (to ~50°) with a-bromo-a-ethylbutyryl bromide (C2H5)2CBrCOBr, see DE 225710 (1910); Frdl. 10, 1160; Chem. Zentralbl. 1910, II, 1008. Patent literature: Slotta, Grundriss der modernen Arzneistoff-Synthese (Stuttgart, 1931); H. P. Kaufmann, Arzneimittel-Synthese (Berlin, 1953).
Properties: Crystals, mp 116-119°. One gram dissolves in about 3000 ml water, 18 ml alcohol, 3 ml chloroform, 14 ml ether. Very sol in boiling alcohol; dissolves in concd sulfuric, nitric and hydrochloric acids, from which it is precipitated on dilution with water. Dissolved by solns of alkali hydroxides.
Melting point: mp 116-119°
Therap-Cat: Sedative, hypnotic.
Keywords: Sedative/Hypnotic; Acylic Ureides.
Carbubarb Carbutamide Carbuterol Cardiotoxin Carfentrazone-ethyl

Carbromal
Skeletal formula of carbromal
Identifiers
CAS number 77-65-6 YesY
PubChem 6488
ChemSpider 6243 YesY
UNII 0Y299JY9V3 YesY
EC number 201-046-6
KEGG D02619 YesY
MeSH carbromal
ChEMBL CHEMBL1697828 YesY
ATC code N05CM04
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C7H13BrN2O2
Molar mass 237.09 g mol−1
Appearance White crystals
Odor Odourless
log P 1.623
Acidity (pKa) 10.69
Basicity (pKb) 3.31
Related compounds
Related ureas Bromisoval
Related compounds
  • 3-Ureidopropionic acid
  • beta-Ureidoisobutyric acid
  • Carbamoyl aspartic acid
  • N-Acetylaspartic acid
  • Aceglutamide
  • N-Acetylglutamic acid
  • Citrulline
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Carbromal is a hypnotic/sedative originally synthesized in 1909 by Bayer.[1]