Carbromal

Carbromal
Skeletal formula of carbromal
Skeletal formula of carbromal
Names
IUPAC name
2-Bromo-N-carbamoyl-2-ethylbutanamide
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.952
EC Number
  • 201-046-6
KEGG
MeSH carbromal
PubChem CID
UNII
CompTox Dashboard (EPA)
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 Odorless
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
ATC code
 N05CM04 (WHO)
Related compounds
Related ureas
 Bromisoval
Related compounds
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] As of 2015, it was still used in Hungary in combination with aminophenazone under the name Demalgon.

Synthesis

Carbromal synthesis:[2][4][5] Literature:[6][7]

Diethylmalonic acid [510-20-3] (1) is decarboxylated to 2-ethylvaleric acid [20225-24-5] (2). The Hell-Volhard-Zelinsky reaction converts this to 2-bromo-2-ethylbutyryl bromide [26074-53-3] (3). Reaction with urea with affords carbromal (4).

See also

  • Acecarbromal
  • Bromisoval
  • Apronal

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. ^ a b 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).
This article is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.