methohexital (CHEBI:102216)

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ChEBI Name	methohexital

ChEBI ID	CHEBI:102216

Definition	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.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:6833

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Formula

C14H18N2O3

Net Charge

Average Mass

262.30430

Monoisotopic Mass

262.13174

InChI

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

CCC#CC(C)C1(CC=C)C(=O)NC(=O)N(C)C1=O

Roles Classification
Biological Role(s):	drug allergen Any drug which causes the onset of an allergic reaction. GABA modulator A substance that does not act as agonist or antagonist but does affect the gamma-aminobutyric acid receptor-ionophore complex. GABA-A receptors 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. (via barbiturates )

Application(s):	intravenous anaesthetic drug allergen Any drug which causes the onset of an allergic reaction. GABA modulator A substance that does not act as agonist or antagonist but does affect the gamma-aminobutyric acid receptor-ionophore complex. GABA-A receptors 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. (via barbiturates )

ChEBI Ontology
Outgoing	methohexital (CHEBI:102216) has role drug allergen (CHEBI:88188) methohexital (CHEBI:102216) has role intravenous anaesthetic (CHEBI:38877) methohexital (CHEBI:102216) is a acetylenic compound (CHEBI:73474) methohexital (CHEBI:102216) is a barbiturates (CHEBI:22693) methohexital (CHEBI:102216) is conjugate acid of methohexital(1−) (CHEBI:60792)

Incoming	methohexital(1−) (CHEBI:60792) is conjugate base of methohexital (CHEBI:102216)

IUPAC Name

1-methyl-5-(1-methylpent-2-yn-1-yl)-5-(prop-2-en-1-yl)pyrimidine-2,4,6(1H,3H,5H)-trione

Synonyms	Sources
(±)-5-allyl-1-methyl-5-(1-methyl-2-pentynyl)barbituric acid	ChemIDplus
5-allyl-1-methyl-5-(1-methyl-2-pentynyl)-2,4,6(1H,3H,5H)-pyrimidinetrione	NIST Chemistry WebBook
5-Allyl-1-methyl-5-(1-methyl-pent-2-ynyl)-pyrimidine-2,4,6-trione	ChEMBL
5-Allyl-5-(3-hexyn-2-yl)-1-methylbarbituric acid	ChemIDplus
α-DL-1-methyl-5-allyl-5-(1'-methylpentyn-2-yl)barbituric acid	NIST Chemistry WebBook
Methohexital	KEGG COMPOUND
Methohexitone	ChemIDplus

Last Modified

04 March 2019

General Comment
2010-12-09	A short-acting barbiturate-type general anaesthetic, methohexital is 2-3 times more potent than thiopental but has a shorter duration of action. It is normally administered as the sodium salt.