基本情報
- CAS
50-09-9- 標準SMILES
CN1C(=O)NC(=O)C(C)(C2=CCCCC2)C1=O- InChIKey
UYXAWHWODHRRMR-UHFFFAOYSA-N- 分子式
- C12H16N2O3
- 平均分子量
- 236.27 g/mol
- 単同位体質量
- 236.11609238
概要
Hexobarbital is a member of the class of barbiturates taht is barbituric acid substituted at N-1 by methyl and at C-5 by methyl and cyclohex-1-enyl groups. It is functionally related to a barbituric acid.
名称と識別子
- 優先名称
- Hexobarbital
- IUPAC
- 5-(cyclohexen-1-yl)-1,5-dimethyl-1,3-diazinane-2,4,6-trione
- 現地名
- ヘキソバルビタール
- 英語名
- HEXOBARBITAL
- 分子式
- C12H16N2O3
- 分子量
- 236.27
名称と別名
HexobarbitalHexobarbitoneMethexenylMethylhexabital56-29-1EvipalEvipanSombucapsSombulexEnhexymalHexobarbitalumHexobarbitonum
名称をさらに表示
5-(1-シクロヘキセン-1-イル)-1,5-ジメチルバルビツル酸バルビドルムトレラン5-(1-シクロヘキセニル)-1,5-ジメチルピリミジン-2,4,6(1H,3H,5H)-トリオンエビパール1-メチル-5-(1-シクロヘキセニル)-5-メチルピリミジン-2,4,6(1H,3H,5H)-トリオンヘキソバルビタール5-(1-シクロヘキセン-1-イル)-1,5-ジメチル-1H,3H,5H-ピリミジン-2,4,6-トリオンエビパンソンブレックス5-(シクロヘキサ-1-エニル)-1,5-ジメチルバルビツル酸ボノドリンイソヘキサビタールソンブカプスメチルヘキサビタールヘキソバルビトン5-メチル-5-(1-シクロヘキセニル)-1-メチル-2-ヒドロキシピリミジン-4,6(1H,5H)-ジオン1,5-ジメチル-5-(シクロヘキセン-1-イル)ピリミジン-2,4,6(1H,3H,5H)-トリオンヘキサンスタブ1,5-ジメチル-5-(1-シクロヘキセニル)ピリミジン-2,4,6(1H,3H,5H)-トリオンHexenalDoricoToleranCitodon
物性
構造計算による物性
- XLogP
- 1.5
- 極性表面積
- 66.5 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 3
- 回転可能結合数
- 1
- 重原子数
- 17
- 形式電荷
- 0
- 複雑度
- 427
実験および物理化学的性質
Drugs
DEA NFLIS-Drug Category -> Depressants and Tranquilizers
Pharmaceuticals -> Barbiturates
LogP
1.98
1.71
Solubility1.51e+00 g/L
Melting Point67.00 °C. @ 760.00 mm Hg
Physical DescriptionSolid
Dissociation Constants8.2
物理化学的性質
- 融点
- 145 · 145-147°
- 沸点
- 378.73 °C · 378.73°C (rough estimate)
- 比重(密度)
- 1.1623 · 1.1623 (rough estimate)
- 屈折率
- 1.546 · 1.5460 (estimate)
- 闪点
- 11 °C · 11 °C
- 貯蔵温度
- 2 · 2-8°C
- 酸解離定数(Pka)
- 7.99 · 7.99±0.10(Predicted)
- 水溶解度
- 434.7 mg/L · 434.7mg/L(25℃)
- EPAの化学物質情報
- Hexobarbital (56-29-1)
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 2 notifications to the ECHA C&L Inventory.
危険有害性情報
Other Safety InformationIMAP assessments - 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(1-cyclohexen-1-yl)-1,5-dimethyl-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (100%)
毒性情報
Health EffectsThey cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive. They cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive.
Exposure RoutesOral
Toxicity Summary
Hexobarbital binds at a distinct binding site associated with a Cl- ionopore at the GABA-A receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.
Signs and SymptomsSymptoms of an overdose typically include sluggishness, incoordination, difficulty in thinking, slowness of speech, faulty judgment, drowsiness or coma, shallow breathing, staggering, and in severe cases coma and death.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
化学と産業
薬理情報
ATC Code
N - Nervous system
N - Nervous system
QN - Nervous system
QN - Nervous system
Protein Binding25%
Pharmacodynamics
Hexobarbital is a barbiturate derivative having hypnotic and sedative effects. It was subsequently used in the 1940s and 1950s as an anesthetic for surgery. Furthermore, the agent also demonstrates a fairly quick onset of action that also possesses a short duration of action. However it can be difficult to control the depth of anesthesia with hexobarbital which makes it quite dangerous, and it has now been replaced by safer drugs in human medicine, usually thiopental would be the barbiturate of choice for this application these days.
Mechanism of Action
Hexobarbital binds at a distinct binding site associated with a Cl- ionopore at the GABA-A receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.
Metabolism/Metabolites
Hepatic.
Hepatic.
MeSH Pharmacological Classification
Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
Substances that do not act as agonists or antagonists but do affect the GAMMA-AMINOBUTYRIC ACID receptor-ionophore complex. GABA-A receptors (RECEPTORS, GABA-A) appear to have at least three allosteric sites at which modulators act: a site at which BENZODIAZEPINES act by increasing the opening frequency of GAMMA-AMINOBUTYRIC ACID-activated chloride channels; a site at which BARBITURATES act to prolong the duration of channel opening; and a site at which some steroids may act. GENERAL ANESTHETICS probably act at least partly by potentiating GABAergic responses, but they are not included here.
Cellular LocationsCytoplasm
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