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メトヘキシタール

Methohexital

HCID 9034
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
151-83-7
標準SMILES
C=CCC1(C(C)C#CCC)C(=O)NC(=O)N(C)C1=O
InChIKey
NZXKDOXHBHYTKP-UHFFFAOYSA-N
分子式
C14H18N2O3
平均分子量
262.3 g/mol
単同位体質量
262.13174244

概要

Methohexital is a barbiturate, the structure of which is that of barbituric acid substituted at N-1 by a methyl group and at C-5 by allyl and 1-methylpent-2-ynyl groups. It has a role as an intravenous anaesthetic and a drug allergen. It is a member of barbiturates and an acetylenic compound. It is a conjugate acid of a methohexital(1-).

名称と識別子

優先名称
Methohexital
IUPAC
5-hex-3-yn-2-yl-1-methyl-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
現地名
メトヘキシタール
英語名
Methohexital
分子式
C14H18N2O3
分子量
262.3

名称と別名

METHOHEXITALMethohexitone151-83-7MethodrexitoneMetohexitalMethohexitalumMetoesital18652-93-25-Allyl-5-(3-hexyn-2-yl)-1-methylbarbituric acidE5B8ND5IPE(+-)-5-Allyl-1-methyl-5-(1-methyl-2-pentynyl)barbituric acidCHEBI:102216
名称をさらに表示
ブレビタールエナルリニマールブリエタール5-(1-メチル-2-ペンチニル)-1-メチル-5-(2-プロペニル)-2,4,6(1H,3H,5H)-ピリミジントリオン化合物22451メトヘキシトンメトドレキシトンメトヘキシタール1-メチル-5-(1-メチル-2-ペンチニル)-5-(2-プロペニル)バルビツル酸化合物253985-(ヘキサ-3-イン-2-イル)-1-メチル-5-(プロパ-2-エン-1-イル)-1,3-ジアジナン-2,4,6-トリオンBrietalBrevitalMethhexitalcompound22451Compound 22451Compound 25398Methohexital solution
5-Allyl-1-methyl-5-(1-methyl-2-pentynyl)-2,4,6(1H,3H,5H)-pyrimidinetrioneDTXSID10232875-Allyl-1-methyl-5-(1-methyl-pent-2-ynyl)-pyrimidine-2,4,6-trione5-(hex-3-yn-2-yl)-1-methyl-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trionealpha-DL-1-Methyl-5-allyl-5-(1'-methylpentyn-2-yl)barbituric acid2,4,6(1H,3H,5H)-Pyrimidinetrione, 1-methyl-5-(1-methyl-2-pentynyl)-5-(2-propenyl)-2,4,6(1H,3H,5H)-Pyrimidinetrione, 1-methyl-5-(1-methyl-2-pentynyl)-5-(2-propenyl)-, (+-)-5-(hex-3-yn-2-yl)-6-hydroxy-3-methyl-5-(prop-2-en-1-yl)-2,3,4,5-tetrahydropyrimidine-2,4-dione

物性

構造計算による物性

XLogP
2.3
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
3
重原子数
19
形式電荷
0
複雑度
497

実験および物理化学的性質

Drugs · 5 件

DEA NFLIS-Drug Category -> Depressants and Tranquilizers

DEA Schedule IV Controlled Substance -> Depressants

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

Pharmaceuticals -> Barbiturates

Pharmaceuticals

SpringerMaterials PropertiesFusion temperature
LogP1.8
Solubility5.24e-02 g/L
Human DrugsBreast Feeding; Lactation; Anesthetics, Intravenous
Physical DescriptionSolid

物理化学的性質

融点
96 °C · 96 °C(Solv: ethanol (64-17-5))
比重(密度)
1.113 · 1.113
貯蔵温度
2 · 2-8°C
溶解性
Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly)
外見
Solid
酸解離定数(Pka)
7.82 · 7.82±0.10(Predicted)
色
White to Off-White

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 · 4 件

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory.

危険有害性情報

Regulatory InformationDEA schedule IV controlled substance
Hazard Classes and CategoriesAcute Tox. 3 (100%)

毒性情報

Treatment · 1 件

Establish an airway and ensure oxygenation and ventilation. Resuscitative measures should be initiated promptly. For hypotension, intravenous fluids should be administered and the patient's legs raised. If desirable increase in blood pressure is not obtained, vasopressor and/or inotropic drugs may be used as dictated by the clinical situation. For convulsions, diazepam intravenously and phenytoin may be required. If the seizures are refractory to diazepam and phenytoin, general anesthesia and paralysis with a neuromuscular blocking agent may be necessary. Protect the patient's airway and support ventilation and perfusion. Meticulously monitor and maintain, within acceptable limits, the patient's vital signs, blood gases, serum electrolytes, etc. Absorption of drugs from the gastrointestinal tract may be decreased by giving activated charcoal, which, in many cases, is more effective than emesis or lavage; consider charcoal instead of or in addition to gastric emptying. Repeated doses of charcoal over time may hasten elimination of some drugs that have been absorbed. Safeguard the patient's airway when employing gastric emptying or charcoal. (L1712)

Health EffectsThey cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive.

化学と産業

薬理情報

ATC Code · 4 件

N - Nervous system

N - Nervous system

QN - Nervous system

QN - Nervous system

Protein Binding73%
Pharmacodynamics · 1 件

Methohexital, a barbiturate, is used for the induction of anesthesia prior to the use of other general anesthetic agents and for induction of anesthesia for short surgical, diagnostic, or therapeutic procedures associated with minimal painful stimuli. Little analgesia is conferred by barbiturates; their use in the presence of pain may result in excitation.

Mechanism of Action · 1 件

Methohexital binds at a distinct binding site associated with a Cl<sup>-</sup> ionopore at the GABA<sub>A</sub> receptor, increasing the duration of time for which the Cl<sup>-</sup> ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.

Biological Half-Life5.6 &plusmn; 2.7 minutes
Metabolism/Metabolites · 2 件

Metabolism occurs in the liver through demethylation and oxidation. Side-chain oxidation is the most important biotransformation involved in termination of biologic activity.

Metabolism occurs in the liver through demethylation and oxidation. Side-chain oxidation is the most important biotransformation involved in termination of biologic activity. Route of Elimination: Excretion occurs via the kidneys through glomerular filtration. Half Life: 5.6 &plusmn; 2.7 minutes

FDA Pharmacological Classification · 5 件

E5B8ND5IPE

METHOHEXITAL

Established Pharmacologic Class [EPC] - Barbiturate

Chemical Structure [CS] - Barbiturates

Methohexital is a Barbiturate.

MeSH Pharmacological Classification · 1 件

Ultrashort-acting anesthetics that are used for induction. Loss of consciousness is rapid and induction is pleasant, but there is no muscle relaxation and reflexes frequently are not reduced adequately. Repeated administration results in accumulation and prolongs the recovery time. Since these agents have little if any analgesic activity, they are seldom used alone except in brief minor procedures. (From AMA Drug Evaluations Annual, 1994, p174)

関連反応

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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

データベース識別子

CAS
151-83-7
PubChem CID
9034
DTXSID
DTXSID1023287
ChEMBL
CHEMBL7413
ChEBI
CHEBI:102216
UNII
E5B8ND5IPE
EC Number
205-798-6
Nikkaji
J10.986J
主な用途
医薬品（低分子化合物）
InChI
1S/C14H18N2O3/c1-5-7-8-10(3)14(9-6-2)11(17)15-13(19)16(4)12(14)18/h6,10H,2,5,9H2,1,3-4H3,(H,15,17,19)
InChIKey
NZXKDOXHBHYTKP-UHFFFAOYSA-N
SMILES
N1(C(=O)NC(=O)C(C1=O)(C(C)C#CCC)CC=C)C
NISTの化学物質情報
Methohexitone(151-83-7)
Adverse Effects · 1 件

The adverse effects of methohexital include respiratory depression, apnea, hiccups, cardiovascular depression, and laryngospasm. In critically ill preload-dependent patients, methohexital may reduce systemic vascular resistance and cardiac output; however, the incidence of these events is low. The ventilatory and cardiovascular depressant effects of methohexital are dose-dependent; however, they vary with the patient's preexisting disease. The respiratory depressant effect may result from both central and peripheral mechanisms. Methohexital can alter upper airway tone, leading to obstruction, and affect the brainstem respiratory centers, resulting in apnea and hypoventilation. Hypotension has also been noted during methohexital administration and is mediated by peripheral vasodilation, resulting in decreased afterload and preload and a negative inotropic effect on the heart. Methohexital is commonly associated with pain when injected into smaller veins. A study demonstrated that dissolving the drug in a lipid emulsion before administration resulted in pain resolution with no change in potency. Mean arterial pressure is not significantly affected after administration of methohexital and appears to be more hemodynamically stable when compared to other agents. As methohexital is a commonly used agent during ECT, it is essential to note that it has dose-dependent anticonvulsant properties and may adversely affect seizure procurement in a subset of patients with high seizure thresholds.

Exposure RoutesParenteral (intramuscular, intravenous). The absolute bioavailability following rectal administration of methohexital is 17%.
Toxicity Summary · 2 件

Signs and Symptoms of Overdose

Methohexital binds at a distinct binding site associated with a Cl<sup>-</sup> ionopore at the GABA<sub>A</sub> receptor, increasing the duration of time for which the Cl<sup>-</sup> ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.

Signs and Symptoms · 1 件

The onset of toxicity following an overdose of intravenously administered methohexital will be within seconds of the infusion. If methohexital is administered rectally or is ingested, the onset of toxicity may be delayed. The manifestations of an ultrashort-acting barbiturate in overdose include central nervous system depression, respiratory depression, hypotension, loss of peripheral vascular resistance, and muscular hyperactivity ranging from twitching to convulsive-like movements. Other findings may include convulsions and allergic reactions.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

安全データ

wgk
WGK 3
ridadr
3249
毒性
An ultra-short-acting i.v. anesthetic. Because its use causes respiratory depression, apnea, and hypotension, establishment and maintenance of airways, oxygen administration, etc. are required. Various allergic responses have sometimes been reported with its use.
hs_code
2933599550
risk_code
11-23/24/25-39/23/24/25
hazard_code
F,T
safety_code
16-36/37-45
hazard_class
6.1(b)
packing_group
III
Hazard Classifications
Acute Tox. 3 Oral
ストレージクラス
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Absorption, Distribution and Excretion · 2 件

The absolute bioavailability following rectal administration of methohexital is 17%.

Excretion occurs via the kidneys through glomerular filtration.

Cellular LocationsMembrane

用途と製造

Uses · 2 件

Use (kg; approx.) in Germany (2009): >10

Methohexital is indicated for use as an intravenous anaesthetic. It has also been commonly used to induce deep sedation. It is only used in hospital or similar settings, under strict supervision.

応用分野 · 1 件

使用Methohexital is a short-acting barbiturate used as a sedative. Methohexital is used an anesthetic for oral surgery and dentistry and is also used to induce anesthesia prior to electroconvulsive therapy (ECT). Methohexital is a Controlled Substance.

サプライヤー17 社

艾吉析科技（上海）有限公司17717235263 · [email protected]
咸宁深蓝生物医药研发有限公司18171815831 · [email protected]
上海丽康新材料有限公司+86-16631818819 +86-17736933208 · [email protected]
青岛海智微元生物科技有限公司18317699790 18317699790 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
艾吉析科技（上海）有限公司17717235263 17717235263 · [email protected]
陕西缔都医药化工有限公司029-029-81120477 17792793610 · [email protected]
武汉沃格达生物科技有限公司15071299552 · [email protected]
上海相辉医药科技有限公司[email protected]
河南天孚化工有限公司+86-0371-55170693 +86-19937530512 · [email protected]
XIAMEN AMITY INDUSTRY AND TRADE CO., LTD.+8618950047208 · [email protected]
重庆卡兰医药有限公司[email protected]
上海将牧生物科技有限公司+8615821988213 · [email protected]
南京世洲生物科技有限公司025-85560043 13675144456 · [email protected]
AFINE CHEMICALS LIMITED+86-571-85134551 +86-18958018566 · [email protected]
Shaanxi Dideu Medichem Co. Ltd+86-17392712779 · [email protected]
湖北清北云研医药科技有限责任公司18162595016; 18162595016 · [email protected]

補足説明

定義ChEBI: A barbiturate, the structure of which is that of barbituric acid substituted at N-1 by a methyl group and at C-5 by allyl and 1-methylpent-2-ynyl groups.