アロバルビタール
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/11/29 11:33:15」(JST)
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Allobarbital
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Systematic (IUPAC) name |
5,5-diprop-2-enyl-1,3-diazinane-2,4,6-trione
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Clinical data |
Legal status |
- CA: Schedule IV
- DE: Anlage III
- US: Schedule IV
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Identifiers |
CAS Number |
52-43-7 Y |
ATC code |
N05CA21 |
PubChem |
CID: 5842 |
ChemSpider |
5635 Y |
UNII |
8NT43GG2HA Y |
KEGG |
D02817 Y |
ChEMBL |
CHEMBL267719 Y |
Synonyms |
5,5-Diallylbarbituric acid, Allobarbital |
Chemical data |
Formula |
C10H12N2O3 |
Molecular mass |
208.214 g/mol |
SMILES
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O=C1NC(=O)NC(=O)C1(C\C=C)C\C=C
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InChI
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InChI=1S/C10H12N2O3/c1-3-5-10(6-4-2)7(13)11-9(15)12-8(10)14/h3-4H,1-2,5-6H2,(H2,11,12,13,14,15) Y
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Key:FDQGNLOWMMVRQL-UHFFFAOYSA-N Y
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Y (what is this?) (verify) |
Allobarbital, also known as allobarbitone and branded as Cibalgine or Dial-Ciba (in combination with ethyl carbamate), is a barbiturate derivative invented in 1912 by Ernst Preiswerk and Ernst Grether working for CIBA. It was used primarily as an anticonvulsant[1] although it has now largely been replaced by newer drugs with improved safety profiles. Other uses for allobarbital included as an adjutant to boost the activity of analgesic drugs, and use in the treatment of insomnia and anxiety.
Allobarbital was never particularly widely used compared to better known barbiturates such as phenobarbital and secobarbital, although it saw more use in some European countries such as Bulgaria and Slovakia,[2] and is still used in for example Poland, but only as compound.[3]
References
- ^ Chocholova L.; Radil-Weiss, T. (1971). "Effect of allobarbital on focal epilepsy in rats". Physiologia Bohemoslovaca 20 (4): 325–34. PMID 4335127.
- ^ Getova, D.; Georgiev, V. (1987). "GABA-ergic mechanisms in the anticonvulsive activity of newly synthesized barbiturates. I. Effects of barbiturates on the convulsive action of GABA-antagonists". Acta Physiologica et Pharmacologica Bulgarica 13 (3): 43–50. PMID 3439474.
- ^ "APTECZKA BABUNI - KROPLE ŻOŁĄDKOWE KROPLE 20 G" [GRANDMA'S FIRST AID KIT - DROPS - STOMACH DROPS 20 G]. Domzdrowia.pl (in Polish). Archived from the original on October 31, 2007. Retrieved March 10, 2013.
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
- Recognition characteristics of molecularly imprinted microspheres for triazine herbicides using hydrogen-bond array strategy and their analytical applications for corn and soil samples.
- Wu S1, Xu Z, Yuan Q, Tang Y, Zuo X, Lai J.Author information 1School of Chemistry & Environment, South China Normal University, Guangzhou 510006, China.AbstractThe homogeneous molecularly imprinted microspheres (MIMs) based on a biologically inspired hydrogen-bond array were prepared using allobarbital as the novel functional monomer and divinylbenzene as the cross-linker. The host-guest binding characteristics were examined by molecular simulation and infrared spectroscopy. The resultant MIMs were evaluated using high performance liquid chromatography and solid-phase extraction. The results obtained demonstrate that the good imprinting effect and the excellent selectivity of MIMs are mainly due to the interaction involving the formation of three-point hydrogen bond between host and guest. The complete baseline separation was obtained for five triazine analogues and a metabolite on the MIM HPLC column. The MIMs were further successfully used as a specific sorbent for selective extraction of simetryne from corn and soil samples by molecularly imprinted solid phase extraction. Detection limits and recoveries were 5.8 μg/kg and 0.14 μg/kg and 87.4-105% and 94.6-101% for simetryne in corn and soil sample, respectively.
- Journal of chromatography. A.J Chromatogr A.2011 Mar 11;1218(10):1340-6. doi: 10.1016/j.chroma.2011.01.008. Epub 2011 Jan 11.
- The homogeneous molecularly imprinted microspheres (MIMs) based on a biologically inspired hydrogen-bond array were prepared using allobarbital as the novel functional monomer and divinylbenzene as the cross-linker. The host-guest binding characteristics were examined by molecular simulation and inf
- PMID 21269632
- [Studies on the structure-activity relationship of allyl substituted oxopyrimidines searching for the novel antagonist or agonist of barbiturates to the sleep mechanism based on the uridine receptor theory--barbituric acid to uridine (part I)].
- Yamamoto I.Author information Faculty of Pharmaceutical Sciences, Hokuriku University, Kanazawa 920-1181, Japan. iyamamoto@phoenix.ac.jpAbstractThirty-six allyl substituted oxopyrimidine analogues such as barbituric acid (BA), barbiturates, uracil, thymine, and related derivatives including 13 new compounds were synthesized and their pharmacologic effects ([hypnotic activity, anticonvulsant activity against pentylentetrazol (PTZ)-induced seizures, and LD(50)]) and interactions with the barbiturates were evaluated in mice and rats. The results are briefly and parially summarized as follows. BA prolonged pentobarbital (PB)-induced sleep and had some central depressant effects. N,5,5-triallyl-BA exhibited some hypnotic and anticonvulsant activities, although the other 5,N-allyl-compounds did not show any activity except for allobarbital (AlloB). N-allyl-BA, 5-allyl-BA, N(1),N(3),5-triallyl-BA, N,5,5-triallyl-BA, and N(1),N(3),5,5-tetraallyl-BA also prolonged PB-induced sleep. Interestingly, N,5,5-triallyl-BA was the most potent in the interaction with AlloB, phenobarbital (PheB), amobarbital (AB), PB, and thiopental (TP) but not barbital (B). N(1),N(3),5,5-tetraallyl-BA prolonged AlloB-, PB-, and AB-induced sleep but not B-, PheB-, and TP-induced sleep. N(1),N(3),5-triallyl-B prolonged only PB- and TP-induced sleep. 5,5-diallyl-BA prolonged PheB- and TP-induced sleep. N,5-diallyl-BA prolonged only TP-induced sleep. In contrast, BA and N(1),N(3),5-triallyl-AB tended to antagonize AlloB, AB, and B. N(1),N(3),5,5-tetraallyl-BA also slightly antagonized B, PheB, and TP. 5,5-diallyl-BA antagonized only AB. The prolonging effects of BA, N,5,5-triallyl-BA, and N(1),N(3),5,5-tetraallyl-BA on PB-induced sleep were dose dependent. These results indicate that the position and number of allyl groups substituted on the structure of BA play an important role in their depressant activities. This review deals with the structure-activity relationship of allyl-substituted oxopyrimidines as part of our search for antagonists and agonists of barbiturates as well as their mechanisms of action.
- Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.Yakugaku Zasshi.2005 Jan;125(1):73-120.
- Thirty-six allyl substituted oxopyrimidine analogues such as barbituric acid (BA), barbiturates, uracil, thymine, and related derivatives including 13 new compounds were synthesized and their pharmacologic effects ([hypnotic activity, anticonvulsant activity against pentylentetrazol (PTZ)-induced se
- PMID 15635282
- Application of atmospheric pressure chemical ionisation mass spectrometry in the analysis of barbiturates by high-speed analytical countercurrent chromatography.
- Jones JJ1, Kidwell H, Games DE.Author information 1Mass Spectrometry Research Unit, University of Wales Swansea, Grove Building, Singleton Park, Swansea SA2 8PP, Wales, UK. 147437@swan.ac.ukAbstractFour barbiturates (barbital, allobarbital, phenobarbital and butalbital) were analysed using high-speed analytical countercurrent chromatography (HSACCC) and high-performance liquid chromatography (HPLC) interfaced with mass spectrometry, using negative mode atmospheric pressure chemical ionisation (APCI). The polar biphasic solvent system of butyronitrile/acetonitrile/water (1:1:1) was used, in the upper-stationary, lower-mobile mode of operation, at a flow rate of 1 mL/min and a rotational speed of 1200 rpm, equating to an applied "g"-field of 177 g. The fractional stationary phase retention (S(F)) was 0.58. Representative mass spectral data are presented from the HPLC and the HSACCC analyses. Structural information was obtained using source-induced fragmentation at increased source block voltages. The effect of increasing g-field on chromatographic resolution is illustrated using the binary base system of butyronitrile/water (1:1), under electrospray ionisation.
- Rapid communications in mass spectrometry : RCM.Rapid Commun Mass Spectrom.2003;17(14):1565-72.
- Four barbiturates (barbital, allobarbital, phenobarbital and butalbital) were analysed using high-speed analytical countercurrent chromatography (HSACCC) and high-performance liquid chromatography (HPLC) interfaced with mass spectrometry, using negative mode atmospheric pressure chemical ionisation
- PMID 12845581
Japanese Journal
- 新睡眠薬及び睡眠薬拮抗物質の探索研究から睡眠機構研究に辿りつくまで : バルビツール酸からウリジンまで(その1)
- 山本 郁男
- 藥學雜誌 125(1), 73-120, 2005-01-01
- 睡眠はヒトを含む動物の必須の生理機能あるいは現象であり, 食欲と同じように生きるための本能的な要求でもある. しかしながら, 「動物はなぜ眠るのか」と言う謎は現在でも完全には解明されていない. 一方, この睡眠を妨げる障害を広く不眠症と呼び, 今日, 文明人の5-10人に1人は不眠に悩まされている. このため睡眠薬(催眠薬と書くこともある)の開発研究の歴史は1世紀以上にもなり, これまでに合成され …
- NAID 110003666158
- バルビツール系化合物のラット肝臓における細胞増殖とアポトーシスに対する影響
- 古川 賢,臼田 浩二,藤枝 陽子,田村 啓,宮本 康夫,林 憲一,池山 聖一,御領 政信,岡田 幸助
- The journal of veterinary medical science 62(1), 23-28, s・vi, 2000-01
- … phenobarbital(PB)及びその他バルビツール系化合物の,肝細胞の細胞増殖とアポトーシスに対する影響を検索するために,PB,allobarbital(ALB),barbital sodium(BS)及びbarbituric acid(BA)をラットに7日間投与した.プロモーター活性のないBAでは,著変は認められなかったが,肝発癌プロモーター活性を有するPB,BS及びALSでは,肝肥大が惹起された.肝肥大はPB及びBSでは酵素誘導と細胞増殖に起因し,ALBでは酵素誘導に起因していた.これら3剤はともに …
- NAID 110003920393
Related Links
- Allobarbital, also known as allobarbitone and branded as Cibalgine or Dial-Ciba (in combination with ethyl carbamate), is a barbiturate derivative invented in 1912 by Ernst Preiswerk and Ernst Grether working for CIBA. It was used primarily as ...
- Allobarbital (Dial, Dwuallyl) – organiczny związek chemiczny, pochodna kwasu barbiturowego o profilu działania zależnym od dawki – uspokajającym lub nasennym i średnim czasie działania. Zsyntetyzowany w roku 1912 przez Ernesta ...
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エタロバルビタール