Carbromal

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Contents

Carbromal
Skeletal formula of carbromal Carbromal.svg
Skeletal formula of carbromal
Names
IUPAC name
2-Bromo-N-carbamoyl-2-ethylbutanamide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.952 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-046-6
KEGG
MeSH carbromal
PubChem CID
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) Yes check.svgY
    Key: OPNPQXLQERQBBV-UHFFFAOYSA-N Yes check.svgY
  • CCC(Br)(CC)C(=O)NC(N)=O
Properties
C7H13BrN2O2
Molar mass 237.097 g·mol−1
AppearanceWhite 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] As of 2015, it was still used in Hungary in combination with aminophenazone under the name Demalgon.

Synthesis

Carbromal synthesis: Literature: Carbromal synthesis.svg
Carbromal synthesis: Literature:

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. 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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