From Wikipedia, the free encyclopedia
Carbromal
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Names
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IUPAC name
2-Bromo-N-carbamoyl-2-ethylbutanamide
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Identifiers
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ChEMBL
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ChemSpider
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ECHA InfoCard
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100.000.952
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EC Number
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KEGG
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MeSH
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carbromal
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UNII
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InChI=1S/C7H13BrN2O2/c1-3-7(8,4-2)5(11)10-6(9)12/h3-4H2,1-2H3,(H3,9,10,11,12) YKey: OPNPQXLQERQBBV-UHFFFAOYSA-N Y
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Properties
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C7H13BrN2O2
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Molar mass
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237.097 g·mol−1
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Appearance
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White crystals
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Odor
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Odourless
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Density
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1.544 g/cm3
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Melting point
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119 °C (246 °F; 392 K)
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Soluble
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Solubility
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soluble in chloroform, ether, acetone, benzene
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log P
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1.623
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Acidity (pKa)
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10.69
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Basicity (pKb)
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3.31
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Structure
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rhombic
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Pharmacology
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N05CM04 (WHO)
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Related compounds
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Related ureas
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Bromisoval
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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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Chemical compound
Carbromal is a hypnotic/sedative originally synthesized in 1909 by Bayer.[1]
Synthesis
Diethylmalonic acid is decarboxylated to 2-ethylvaleric acid then converted via a Hell-Volhard-Zelinsky reaction to α-bromo-α-ethylbutyryl bromide. Reaction with urea with affords carbromal (4).
See also
References
- ^ DE 225710
- ^ Frdl. 10, 1160
- ^ Chem. Zentralbl. 1910, II, 1008.
- ^ Slotta, Grundriss der modernen Arzneistoff-Synthese (Stuttgart, 1931)
- ^ H. P. Kaufmann, Arzneimittel-Synthese (Berlin, 1953).
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Alcohols | |
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Barbiturates | |
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Benzodiazepines | |
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Carbamates | |
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Flavonoids | |
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Imidazoles | |
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Kava constituents | |
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Monoureides | |
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Neuroactive steroids | |
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Nonbenzodiazepines | |
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Phenols | |
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Piperidinediones | |
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Pyrazolopyridines | |
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Quinazolinones | |
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Volatiles/gases | |
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Others/unsorted |
- 3-Hydroxybutanal
- α-EMTBL
- AA-29504
- Alogabat
- Avermectins (e.g., ivermectin)
- Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide)
- Carbamazepine
- Chloralose
- Chlormezanone
- Clomethiazole
- Darigabat
- DEABL
- Deuterated etifoxine
- Dihydroergolines (e.g., dihydroergocryptine, dihydroergosine, dihydroergotamine, ergoloid (dihydroergotoxine))
- DS2
- Efavirenz
- Etazepine
- Etifoxine
- Fenamates (e.g., flufenamic acid, mefenamic acid, niflumic acid, tolfenamic acid)
- Fluoxetine
- Flupirtine
- Hopantenic acid
- KRM-II-81
- Lanthanum
- Lavender oil
- Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol)
- Loreclezole
- Menthyl isovalerate (validolum)
- Monastrol
- Niacin
- Niacinamide
- Org 25,435
- Phenytoin
- Propanidid
- Retigabine (ezogabine)
- Safranal
- Seproxetine
- Stiripentol
- Sulfonylalkanes (e.g., sulfonmethane (sulfonal), tetronal, trional)
- Terpenoids (e.g., borneol)
- Topiramate
- Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic acid, valerenol)
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