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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/11/11 19:00:24」(JST)
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Carbromal
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Names |
IUPAC name
2-Bromo-N-carbamoyl-2-ethylbutanamide
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Identifiers |
CAS Registry Number
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77-65-6 Y |
ATC code |
N05CM04 |
ChEMBL |
ChEMBL1697828 Y |
ChemSpider |
6243 Y |
EC number |
201-046-6 |
InChI
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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) Y
Key: OPNPQXLQERQBBV-UHFFFAOYSA-N Y
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Jmol-3D images |
Image
Image |
KEGG |
D02619 Y |
MeSH |
carbromal |
PubChem |
6488 |
SMILES
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CCC(Br)(CC)c(:[o]):[nH]:c(:[nH2]):[o]
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CCC(Br)(CC)C(=O)NC(N)=O
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UNII |
0Y299JY9V3 Y |
Properties |
Chemical formula
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C7H13BrN2O2 |
Molar mass |
237.10 g·mol−1 |
Appearance |
White crystals |
Odor |
Odourless |
log P |
1.623 |
Acidity (pKa) |
10.69 |
Basicity (pKb) |
3.31 |
Related compounds |
Related ureas
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Bromisoval |
Related compounds
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- 3-Ureidopropionic acid
- beta-Ureidoisobutyric acid
- Carbamoyl aspartic acid
- N-Acetylaspartic acid
- Aceglutamide
- N-Acetylglutamic acid
- Citrulline
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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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Infobox references |
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Carbromal is a hypnotic/sedative originally synthesized in 1909 by Bayer.[1]
Synthesis
Carbromal synthesis:
DE 225710 (1910);
[2][3] Patent literature:
[4][5]
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
- Acecarbromal
- Bromisoval
- Apronal
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).
GABAA receptor positive allosteric modulators
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Alcohols |
- Brometone
- Butanol
- Chloralodol
- Chlorobutanol (cloretone)
- Ethanol (drinking alcohol)
- Ethchlorvynol
- Isobutanol
- Isopropanol
- Menthol
- Methanol
- Methylpentynol
- Pentanol
- Petrichloral
- Propanol
- tert-Butanol (2M2P)
- tert-Pentanol (2M2B)
- Tribromoethanol
- Trichloroethanol
- Triclofos
- Trifluoroethanol
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Barbiturates |
- (-)-DMBB
- Allobarbital
- Alphenal
- Amobarbital
- Aprobarbital
- Barbexaclone
- Barbital
- Benzobarbital
- Benzylbutylbarbiturate
- Brallobarbital
- Brophebarbital
- Butabarbital/Secbutabarbital
- Butalbital
- Buthalital
- Butobarbital
- Butallylonal
- Carbubarb
- CP-1414S
- Crotylbarbital
- Cyclobarbital
- Cyclopentobarbital
- Difebarbamate
- Enallylpropymal
- Ethallobarbital
- Eterobarb
- Febarbamate
- Heptabarb
- Heptobarbital
- Hexethal
- Hexobarbital
- Metharbital
- Methitural
- Methohexital
- Methylphenobarbital
- Narcobarbital
- Nealbarbital
- Pentobarbital
- Phenallymal
- Phenobarbital
- Phetharbital
- Primidone
- Probarbital
- Propallylonal
- Propylbarbital
- Proxibarbital
- Reposal
- Secobarbital
- Sigmodal
- Spirobarbital
- Talbutal
- Tetrabamate
- Tetrabarbital
- Thialbarbital
- Thiamylal
- Thiobarbital
- Thiobutabarbital
- Thiopental
- Thiotetrabarbital
- Valofane
- Vinbarbital
- Vinylbital
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Benzodiazepines |
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Carbamates |
- Carisbamate
- Carisoprodol
- Clocental
- Cyclarbamate
- Difebarbamate
- Emylcamate
- Ethinamate
- Febarbamate
- Felbamate
- Hexapropymate
- Lorbamate
- Mebutamate
- Meprobamate
- Nisobamate
- Pentabamate
- Phenprobamate
- Procymate
- Styramate
- Tetrabamate
- Tybamate
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Flavonoids |
- 6-Methylapigenin
- Ampelopsin (dihydromyricetin)
- Apigenin
- Baicalein
- Baicalin
- Catechin
- EGC
- EGCG
- Hispidulin
- Linarin
- Luteolin
- Rc-OMe
- Skullcap constituents (e.g., baicalin)
- Wogonin
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Imidazoles |
- Etomidate
- Metomidate
- Propoxate
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Kava constituents |
- 10-Methoxyyangonin
- 11-Methoxyyangonin
- 11-Hydroxyyangonin
- Desmethoxyyangonin
- 11-Methoxy-12-hydroxydehydrokavain
- 7,8-Dihydroyangonin
- Kavain
- 5-Hydroxykavain
- 5,6-Dihydroyangonin
- 7,8-Dihydrokavain
- 5,6,7,8-Tetrahydroyangonin
- 5,6-Dehydromethysticin
- Methysticin
- 7,8-Dihydromethysticin
- Yangonin
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Monoureides |
- Acecarbromal
- Apronal (apronalide)
- Bromisoval
- Carbromal
- Capuride
- Ectylurea
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Neuroactive steroids |
- Acebrochol
- Allopregnanolone
- Alfadolone
- Alfaxalone
- 3α-Androstanediol
- Androstenol
- Androsterone
- Cholesterol
- DHDOC
- 3α-DHP
- 5α-DHP
- 5β-DHP
- Etiocholanolone
- Ganaxolone
- Hydroxydione
- Minaxolone
- Org 20599
- Org 21465
- Pregnanolone (eltanolone)
- Progesterone
- Renanolone
- SAGE-217
- SAGE-689
- THDOC
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Nonbenzodiazepines |
- β-Carbolines: Abecarnil
- Gedocarnil
- Harmane
- SL-651,498
- ZK-93423; Cyclopyrrolones: Eszopiclone
- Pagoclone
- Pazinaclone
- Suproclone
- Suriclone
- Zopiclone; Imidazopyridines: Alpidem
- DS-1
- Necopidem
- Saripidem
- Zolpidem; Pyrazolopyrimidines: Divaplon
- Fasiplon
- Indiplon
- Lorediplon
- Ocinaplon
- Panadiplon
- Taniplon
- Zaleplon; Others: Adipiplon
- CGS-8216
- CGS-9896
- CGS-13767
- CGS-20625
- CL-218,872
- CP-615,003
- CTP-354
- ELB-139
- GBLD-345
- JM-1232
- L-838,417
- Lirequinil (Ro41-3696)
- NS-2664
- NS-2710
- NS-11394
- Pipequaline
- ROD-188
- RWJ-51204
- SB-205,384
- SX-3228
- TP-003
- TPA-023
- TP-13
- U-89843A
- U-90042
- Y-23684
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Phenols |
- Fospropofol
- Propofol
- Thymol
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Piperidinediones |
- Glutethimide
- Methyprylon
- Piperidione
- Pyrithyldione
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Pyrazolopyridines |
- Cartazolate
- Etazolate
- ICI-190,622
- Tracazolate
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Quinazolinones |
- Afloqualone
- Cloroqualone
- Diproqualone
- Etaqualone
- Mebroqualone
- Mecloqualone
- Methaqualone
- Methylmethaqualone
- Nitromethaqualone
- SL-164
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Volatiles/gases |
- Acetone
- Acetophenone
- Acetylglycinamide chloral hydrate
- Aliflurane
- Benzene
- Butane
- Butylene
- Centalun
- Chloral
- Chloral betaine
- Chloral hydrate
- Chloroform
- Cryofluorane
- Desflurane
- Dichloralphenazone
- Dichloromethane
- Diethyl ether
- Enflurane
- Ethyl chloride
- Ethylene
- Fluroxene
- Gasoline
- Halopropane
- Halothane
- Isoflurane
- Kerosine
- Methoxyflurane
- Methoxypropane
- Nitric oxide
- Nitrogen
- Nitrous oxide
- Norflurane
- Paraldehyde
- Propane
- Propylene
- Roflurane
- Sevoflurane
- Synthane
- Teflurane
- Toluene
- Trichloroethane (methyl chloroform)
- Trichloroethylene
- Vinyl ether
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Others/unsorted |
- 3-Hydroxybutanal
- α-EMTBL
- AA-29504
- Avermectins (e.g., ivermectin)
- Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide)
- Carbamazepine
- Chloralose
- Chlormezanone
- Clomethiazole
- DEABL
- 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
- Lanthanum
- Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol)
- Loreclezole
- Menthyl isovalerate (validolum)
- Monastrol
- Niacin
- Nicotinamide (niacinamide)
- Org 25,435
- Phenytoin
- Propanidid
- Retigabine (ezogabine)
- Safranal
- SAGE-547
- Seproxetine
- Stiripentol
- Sulfonylalkanes (e.g., sulfonmethane (sulfonal), tetronal, trional)
- Terpenoids (e.g., borneol)
- Topiramate
- Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic acid, valerenol)
- Unsorted benzodiazepine site PAMs: MRK-409 (MK-0343)
- TCS-1105
- TCS-1205
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See also: GABAergics
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English Journal
- Regional potassium distribution in the brain in forensic relevant types of intoxication preliminary morphometric evaluation using a histochemical method.
- Oehmichen M1, Ochs U, Meissner C.
- Neurotoxicology.Neurotoxicology.2001 Feb;22(1):99-107.
- A histochemical-morphometric method was used to measure potassium (K+) levels in gray and white matter of rats following sublethal intoxication with 11 different neurotoxic compounds of high forensic significance. Six rats were each given a single substance applied intraperitoneally, the same dosage
- PMID 11307856
- [Periodic discharges of sleep spindles with placebo and zopiclone].
- Spieweg I1, Sanders S, Kubicki S.
- EEG-EMG Zeitschrift für Elektroenzephalographie, Elektromyographie und verwandte Gebiete.EEG EMG Z Elektroenzephalogr Elektromyogr Verwandte Geb.1992 Dec;23(4):215-20.
- According to our experiences (parietal) sleep spindles often show a periodical appearance. Successive sleep spindles in series have a distance of about four seconds. In 95% the duration of such series of sleep spindles is not longer than 40 s, so that there appears no more than ten successive period
- PMID 1486827
- Determination of meprobamate in pharmaceutical dosage forms also containing carbromal by liquid chromatography and indirect photometric detection.
- Bechet I1, Ceccato A, Hubert P, Herné P, Crommen J.
- Journal of pharmaceutical and biomedical analysis.J Pharm Biomed Anal.1992 Oct-Dec;10(10-12):995-9.
- In a pharmaceutical form also containing carbromal, meprobamate could not be quantified selectively by classical methods described in pharmacopoeias due to a significant interference from carbromal. Consequently, reversed-phase HPLC methods have been developed to separate the two active ingredients
- PMID 1363691
Japanese Journal
- (2-Bromoacyl)ureidesの生体内脱ブロム反応に関する研究(第2報) : (2-Bromopropionyl)ureaおよび(2-Bromocaproyl)ureaの脱ブロムについて
- α-Bromoacylureidesの生体内脱ブロム反応に関する研究(第1報) : Bromural, CarbromalおよびAcetylcarbromalの脱ブロムについて
- Purpuric eruptions associated with use of carbromal and meprobamate
Related Links
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