Carbromal

Carbromal
Names
IUPAC name
2-Bromo-N-carbamoyl-2-ethylbutanamide
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.952
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EC Number
  • 201-046-6
KEGG
MeSH carbromal
PubChem CID
UNII
InChI
  • InChI=1S/C7H13BrN2O2/c1-3-7(8,4-2)5(11)10-6(9)12/h3-4H2,1-2H3,(H3,9,10,11,12) checkY
    Key: OPNPQXLQERQBBV-UHFFFAOYSA-N checkY
SMILES
  • CCC(Br)(CC)C(=O)NC(N)=O
Properties
Chemical formula
 C7H13BrN2O2
Molar mass 237.097 g·mol−1
Appearance White crystals
Odor Odourless
Density 1.544 g/cm3
Melting point 119 °C (246 °F; 392 K)
Solubility in water
 Soluble
Solubility soluble in chloroform, ether, acetone, benzene
log P 1.623
Acidity (pKa) 10.69
Basicity (pKb) 3.31
Structure
Crystal structure
 rhombic
Pharmacology
N05CM04 (WHO)
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 otherwise noted, 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 and subsequently marketed as Adalin.[1][2] The drug was later sold by Parke-Davis in combination with pentobarbital, under the name Carbrital.[3]

Synthesis

Carbromal synthesis:[2][4][5] Patent literature:[6][7]

Diethylmalonic acid is decarboxylated to 2-ethylvaleric acid then converted via a Hell-Volhard-Zelinsky reaction to α-bromo-α-ethylbutyryl bromide. Reaction with urea with affords carbromal (4).

See also

References

  1. ↑ Borrie P (March 1955). "A purpuric drug eruption caused by carbromal". British Medical Journal. 1 (4914): 645–6. doi:10.1136/bmj.1.4914.645. PMC 2061381. PMID 13230580.
  2. 1 2 DE 22571, "Verfahren dur Darstellung von Bromodiäthylacetylharnstoff [Method for the preparation of bromodiethylacetylurea]", published 1910-09-17, assigned to Friedrich Bayer & Co.
  3. ↑ Physicians' Desk Reference (33 ed.). Oradell, N.J.: Medical Economics Co. 1979. p. 1266. ISBN 0-87489-999-0. OCLC 4636066.
  4. ↑ Frdl. 10, 1160
  5. ↑ Chem. Zentralbl. 1910, II, 1008.
  6. ↑ Slotta H (1931). Bauer KH (ed.). Grundriss der modernen Arzneistoff‐Synthese. Stuttgart: Verlag Ferd. Enke.
  7. ↑ H. P. Kaufmann, Arzneimittel-Synthese (Berlin, 1953).
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