CHEBI:2673 - amobarbital

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ChEBI Name amobarbital
ChEBI ID CHEBI:2673
Definition A member of the class of barbiturates that is pyrimidine-2,4,6(1H,3H,5H)-trione substituted by a 3-methylbutyl and an ethyl group at position 5. Amobarbital has been shown to exhibit sedative and hypnotic properties.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C11H18N2O3
Net Charge 0
Average Mass 226.27230
Monoisotopic Mass 226.13174
InChI InChI=1S/C11H18N2O3/c1-4-11(6-5-7(2)3)8(14)12-10(16)13-9(11)15/h7H,4-6H2,1-3H3,(H2,12,13,14,15,16)
InChIKey VIROVYVQCGLCII-UHFFFAOYSA-N
SMILES CCC1(CCC(C)C)C(=O)NC(=O)NC1=O
Roles Classification
Biological Role(s): 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): 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 )
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ChEBI Ontology
Outgoing amobarbital (CHEBI:2673) is a barbiturates (CHEBI:22693)
IUPAC Name
5-ethyl-5-(3-methylbutyl)pyrimidine-2,4,6(1H,3H,5H)-trione
Synonyms Sources
5-ethyl-5-(3-methylbutyl)-2,4,6(1H,3H,5H)-pyrimidinetrione NIST Chemistry WebBook
5-ethyl-5-(3-methylbutyl)barbituric acid NIST Chemistry WebBook
5-ethyl-5-isoamylbarbituric acid NIST Chemistry WebBook
5-ethyl-5-isopentylbarbituric acid NIST Chemistry WebBook
Amobarbital KEGG COMPOUND
amylobarbitone ChemIDplus
amytal ChemIDplus
barbamil ChemIDplus
barbamyl NIST Chemistry WebBook
Manual Xrefs Databases
184 DrugCentral
Amobarbital Wikipedia
C07536 KEGG COMPOUND
CPD-5742 MetaCyc
D00555 KEGG DRUG
DB01351 DrugBank
HMDB0015440 HMDB
US3507960 Patent
View more database links
Registry Numbers Types Sources
211172 Reaxys Registry Number Reaxys
281708 Gmelin Registry Number Gmelin
57-43-2 CAS Registry Number ChemIDplus
57-43-2 CAS Registry Number NIST Chemistry WebBook
Last Modified
22 February 2017
General Comment
2014-05-12 Amobarbital can be found in blood and urine samples of individuals who have taken this drug.