Carbromal

Summary

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]

Carbromal
Skeletal formula of carbromal
Names
IUPAC name
2-Bromo-N-carbamoyl-2-ethylbutanamide
Identifiers
  • 77-65-6 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL1697828 checkY
ChemSpider
  • 6243 checkY
ECHA InfoCard 100.000.952 Edit this at Wikidata
EC Number
  • 201-046-6
KEGG
  • D02619 checkY
MeSH carbromal
  • 6488
UNII
  • 0Y299JY9V3 checkY
  • DTXSID8020252 Edit this at Wikidata
  • 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
  • CCC(Br)(CC)C(=O)NC(N)=O
Properties
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)
Soluble
Solubility soluble in chloroform, ether, acetone, benzene
log P 1.623
Acidity (pKa) 10.69
Basicity (pKb) 3.31
Structure
rhombic
Pharmacology
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

Synthesis edit

 
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 edit

References edit

  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).