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Contents

   



(Top)
  


1 Synthesis  




2 See also  




3 References  













Carbromal






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From Wikipedia, the free encyclopedia
  

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 Edit this at Wikidata
EC Number
  • 201-046-6
KEGG
MeSH carbromal

PubChem CID
UNII

CompTox Dashboard (EPA)

  • 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

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

ATC code

 N05CM04 (WHO)
Related compounds

Related ureas

 Bromisoval

Related compounds
  • 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[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.
  • ^ a b DE 22571, "Verfahren dur Darstellung von Bromodiäthylacetylharnstoff [Method for the preparation of bromodiethylacetylurea]", published 1910-09-17, assigned to Friedrich Bayer & Co. 
  • ^ Physicians' Desk Reference (33 ed.). Oradell, N.J.: Medical Economics Co. 1979. p. 1266. ISBN 0-87489-999-0. OCLC 4636066.
  • ^ Frdl. 10, 1160
  • ^ Chem. Zentralbl. 1910, II, 1008.
  • ^ Slotta H (1931). Bauer KH (ed.). Grundriss der modernen Arzneistoff-Synthese. Stuttgart: Verlag Ferd. Enke.
  • ^ H. P. Kaufmann, Arzneimittel-Synthese (Berlin, 1953).
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    • Retrieved from "https://en.wikipedia.org/w/index.php?title=Carbromal&oldid=1195113474"
    Categories: 
    ●Hypnotics
     ●Sedatives
     ●Ureas
     ●Organobromides
     ●GABAA receptor positive allosteric modulators
     ●Drugs developed by Bayer
     ●Sedative stubs
     Hidden categories: 
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