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Methohexital

HCID 9034
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
151-83-7
표준 SMILES
C=CCC1(C(C)C#CCC)C(=O)NC(=O)N(C)C1=O
InChIKey
NZXKDOXHBHYTKP-UHFFFAOYSA-N
분자식
C14H18N2O3
평균 분자량
262.3 g/mol
단동위원소 질량
262.13174244

개요

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-).

이름 및 식별자

우선 이름
Methohexital
IUPAC
5-hex-3-yn-2-yl-1-methyl-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
영어명
Methohexital
분자식
C14H18N2O3
분자량
262.3

이름 및 동의어

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
이름 더 보기
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

데이터베이스 식별자

CAS
151-83-7
PubChem CID
9034
DTXSID
DTXSID1023287

물성

구조 계산 물성

XLogP
2.3
극성 표면적
66.5 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
3
회전 가능 결합 수
3
무거운 원자 수
19
형식 전하
0
복잡도
497

실험 및 물리화학적 성질

Drugs · 5건

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

물리화학적 성질

녹는점
96 °C · 96 °C(Solv: ethanol (64-17-5))
밀도
1.113 · 1.113
저장 조건
2 · 2-8°C
용해도
아세토니트릴(약간 용해됨), 클로로포름(약간 용해됨), 메탄올(약간 용해됨)
물리적 상태
고체
산도 계수 (pKa)
7.82 · 7.82±0.10(Predicted)
색상
흰색에서 황백색까지

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

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.

유해성 정보

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

독성 정보

Treatment · 1건

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.

화학 및 산업

약리 정보

ATC Code · 4건

N - Nervous system

N - Nervous system

QN - Nervous system

QN - Nervous system

Protein Binding73%
Pharmacodynamics · 1건

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 · 1건

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 · 2건

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 · 5건

E5B8ND5IPE

METHOHEXITAL

Established Pharmacologic Class [EPC] - Barbiturate

Chemical Structure [CS] - Barbiturates

Methohexital is a Barbiturate.

MeSH Pharmacological Classification · 1건

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)

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화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
ChEMBL
CHEMBL7413
ChEBI
CHEBI:102216
UNII
E5B8ND5IPE
EC Number
205-798-6
Nikkaji
J10.986J
주요 응용
의약품(소분자)
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
Methohexitone(151-83-7)
Adverse Effects · 1건

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 · 2건

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 · 1건

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

안전 데이터

wgk
WGK 3
ridadr
3249
독성
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 번호
2933599550
risk_code
11-23/24/25-39/23/24/25
hazard_code
F,T
safety_code
16-36/37-45
포장분류
III
위험 등급
6.1(b)
Hazard Classifications
Acute Tox. 3 Oral
스토리지 클래스
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Absorption, Distribution and Excretion · 2건

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

Excretion occurs via the kidneys through glomerular filtration.

Cellular LocationsMembrane

용도 및 제조

Uses · 2건

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.

응용 분야 · 1건

용도Methohexital 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.

공급사17 곳

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]

추가 설명

정의ChEBI: 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.