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Carbromal

Carbromal
Skeletal formula of carbromal
Names
IUPAC name
2-Bromo-N-carbamoyl-2-ethylbutanamide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.952 Edit this at Wikidata
EC Number
  • 201-046-6
KEGG
MeSH carbromal
UNII
  • 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 Odorless
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).

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] 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

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).
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