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Methohexital

HCID 9034
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GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
151-83-7
Standard-SMILES
C=CCC1(C(C)C#CCC)C(=O)NC(=O)N(C)C1=O
InChIKey
NZXKDOXHBHYTKP-UHFFFAOYSA-N
Summenformel
C14H18N2O3
Durchschnittliche Molmasse
262,3 g/mol
Monoisotopische Masse
262,13174244

Überblick

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-).

Namen und Bezeichner

Bevorzugter Name
Methohexital
IUPAC
5-hex-3-yn-2-yl-1-methyl-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
Lokaler Name
Methohexital
Englischer Name
Methohexital
Summenformel
C14H18N2O3
Molmasse
262.3

Namen und Synonyme

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
Weitere Namen anzeigen
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

Datenbank-Bezeichner

CAS
151-83-7

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,3
Polarare Oberfläche (TPSA)
66,5 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
3
Schwere Atome
19
Formalladung
0
Komplexität
497

Experimentelle und physikochemische Eigenschaften

Drugs · 5 Einträge

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

Physikochemische Eigenschaften

Schmelzpunkt
96 °C · 96 °C(Solv: ethanol (64-17-5))
Dichte
1.113 · 1.113
storage temp.
2 · 2-8°C
Löslichkeit
Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

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

Toxikologische Informationen

Treatment · 1 Eintrag

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)

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 4 Einträge

N - Nervous system

N - Nervous system

QN - Nervous system

QN - Nervous system

Protein Binding73%
Pharmacodynamics · 1 Eintrag

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 Eintrag

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 Einträge

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 Einträge

E5B8ND5IPE

METHOHEXITAL

Established Pharmacologic Class [EPC] - Barbiturate

Chemical Structure [CS] - Barbiturates

Methohexital is a Barbiturate.

MeSH Pharmacological Classification · 1 Eintrag

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
PubChem CID
9034
DTXSID
DTXSID1023287
ChEMBL
CHEMBL7413
ChEBI
CHEBI:102216
UNII
E5B8ND5IPE
EC Number
205-798-6
Nikkaji
J10.986J
Aggregatzustand
Solid
pka
7.82 · 7.82±0.10(Predicted)
Farbe
White to Off-White
Major Application
pharmaceutical (small molecule)
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 chemische Informationen
Methohexitone(151-83-7)
Health Effects
They cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive.
Adverse Effects · 1 Eintrag

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 Einträge

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 Eintrag

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

Sicherheitsdaten

wgk
WGK 3
ridadr
3249
hs_code
2933599550
risk_code
11-23/24/25-39/23/24/25
Toxizität
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.
hazard_code
F,T
safety_code
16-36/37-45
hazard_class
6.1(b)
packing_group
III
Speicherklasse
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
Acute Tox. 3 Oral

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)

Absorption, Distribution and Excretion · 2 Einträge

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

Excretion occurs via the kidneys through glomerular filtration.

Cellular LocationsMembrane

Verwendung und Herstellung

Uses · 2 Einträge

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.

Anwendungen · 1 Eintrag

VerwendenMethohexital 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.

Anbieter17 Anbieter

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]

Ergänzende Hinweise

DefinitionChEBI: 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.