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]
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Names | |
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IUPAC name
2-Bromo-N-carbamoyl-2-ethylbutanamide
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Identifiers | |
3D model (JSmol)
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ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.000.952 |
EC Number |
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KEGG | |
MeSH | carbromal |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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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
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Bromisoval |
Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis
editDiethylmalonic 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
editReferences
edit- ^ 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).