carbromal

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{{chembox

| ImageFile = Carbromal.svg

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageName = Skeletal formula of carbromal

| IUPACName = 2-Bromo-N-carbamoyl-2-ethylbutanamide

|Section1={{Chembox Identifiers

| CASNo = 77-65-6

| CASNo_Ref = {{cascite|correct|??}}

| PubChem = 6488

| ChemSpiderID = 6243

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| UNII = 0Y299JY9V3

| UNII_Ref = {{fdacite|correct|FDA}}

| EINECS = 201-046-6

| KEGG = D02619

| KEGG_Ref = {{keggcite|correct|kegg}}

| MeSHName = carbromal

| ChEMBL = 1697828

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| SMILES = CCC(Br)(CC)C(=O)NC(N)=O

| StdInChI = 1S/C7H13BrN2O2/c1-3-7(8,4-2)5(11)10-6(9)12/h3-4H2,1-2H3,(H3,9,10,11,12)

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = OPNPQXLQERQBBV-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

}}

|Section2={{Chembox Properties

| C=7 | H=13 | Br=1 | N=2 | O=2

| Appearance = White crystals

| Odor = Odorless

| Density = 1.544 g/cm³

| MeltingPtC = 119

| Solubility = Soluble

| SolubleOther = soluble in chloroform, ether, acetone, benzene

| LogP = 1.623

| pKa = 10.69

| pKb = 3.31

}}

|Section5={{Chembox Structure

| CrystalStruct = rhombic

}}

|Section6={{Chembox Pharmacology

| ATCCode_prefix = N05

| ATCCode_suffix = CM04

}}

|Section8={{Chembox Related

| OtherFunction_label = ureas

| OtherFunction = Bromisoval

| OtherCompounds = {{unbulleted list|3-Ureidopropionic acid|beta-Ureidoisobutyric acid|Carbamoyl aspartic acid|N-Acetylaspartic acid|Aceglutamide|N-Acetylglutamic acid|Citrulline}}

}}

}}

Carbromal is a hypnotic/sedative originally synthesized in 1909 by Bayer and subsequently marketed as Adalin.{{cite journal | vauthors = Borrie P | title = A purpuric drug eruption caused by carbromal | journal = British Medical Journal | volume = 1 | issue = 4914 | pages = 645–6 | date = March 1955 | pmid = 13230580 | pmc = 2061381 | doi = 10.1136/bmj.1.4914.645 }}{{cite patent|country=DE|number=22571|pubdate=1910-09-17|title=Verfahren dur Darstellung von Bromodiäthylacetylharnstoff [Method for the preparation of bromodiethylacetylurea]|assign=Friedrich Bayer & Co.}} The drug was later sold by Parke-Davis in combination with pentobarbital, under the name Carbrital.{{Cite book|url=https://www.worldcat.org/oclc/4636066|title=Physicians' Desk Reference.|date=1979|publisher=Medical Economics Co|isbn=0-87489-999-0|edition=33|location=Oradell, N.J.|pages=1266|oclc=4636066}} As of 2015, it was still used in Hungary in combination with aminophenazone under the name Demalgon.