Carbromal
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| Names | |
|---|---|
| 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 |
PubChemCID
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| UNII | |
CompTox Dashboard(EPA)
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| Properties | |
| C7H13BrN2O2 | |
| Molar mass | 237.097g·mol−1 |
| Appearance | White crystals |
| Odor | Odourless |
| Density | 1.544 g/cm3 |
| Melting point | 119 °C (246 °F; 392 K) |
| Soluble | |
| Solubility | soluble inchloroform,ether,acetone,benzene |
| logP | 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 theirstandard state(at 25 °C [77 °F], 100 kPa).
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Carbromalis ahypnotic/sedativeoriginally synthesized in 1909 by Bayer and subsequently marketed asAdalin.[1][2]The drug was later sold byParke-Davisin combination withpentobarbital,under the nameCarbrital.[3]
Synthesis[edit]
Diethylmalonic acid [510-20-3] (1) is decarboxylated to 2-ethylvaleric acid [20225-24-5] (2). TheHell-Volhard-Zelinsky reactionconverts this to 2-Bromo-2-Ethylbutyryl Bromide [26074-53-3] (3). Reaction withureawith affords carbromal (4).
See also[edit]
References[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.PMC2061381.PMID13230580.
- ^abDE 22571,"Verfahren dur Darstellung von Bromodiäthylacetylharnstoff [Method for the preparation of bromodiethylacetylurea]", published 1910-09-17, assigned toFriedrich Bayer & Co.
- ^Physicians' Desk Reference(33 ed.). Oradell, N.J.: Medical Economics Co. 1979. p. 1266.ISBN0-87489-999-0.OCLC4636066.
- ^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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