CHEBI:9073 - secobarbital

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ChEBI Name secobarbital
ChEBI ID CHEBI:9073
Definition A member of the class of barbiturates that is barbituric acid in which the hydrogens at position 5 are substituted by prop-2-en-1-yl and pentan-2-yl groups.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C12H18N2O3
Net Charge 0
Average Mass 238.28300
Monoisotopic Mass 238.132
InChI InChI=1S/C12H18N2O3/c1-4-6-8(3)12(7-5-2)9(15)13-11(17)14-10(12)16/h5,8H,2,4,6-7H2,1,3H3,(H2,13,14,15,16,17)
InChIKey KQPKPCNLIDLUMF-UHFFFAOYSA-N
SMILES CCCC(C)C1(CC=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): anaesthesia adjuvant
Any substance that possesses little anaesthetic effect by itself, but which enhances or potentiates the anaesthetic action of other drugs when given at the same time.
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 )
sedative
A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing secobarbital (CHEBI:9073) has functional parent barbituric acid (CHEBI:16294)
secobarbital (CHEBI:9073) has role anaesthesia adjuvant (CHEBI:60807)
secobarbital (CHEBI:9073) has role GABA modulator (CHEBI:50268)
secobarbital (CHEBI:9073) has role sedative (CHEBI:35717)
secobarbital (CHEBI:9073) is a barbiturates (CHEBI:22693)
secobarbital (CHEBI:9073) is conjugate acid of secobarbital (1−) (CHEBI:60810)
Incoming secobarbital (1−) (CHEBI:60810) is conjugate base of secobarbital (CHEBI:9073)
IUPAC Name
5-(pentan-2-yl)-5-(prop-2-en-1-yl)-pyrimidine-2,4,6(1H,3H,5H)-trione
INNs Sources
secobarbital ChemIDplus
secobarbitalum ChemIDplus
Synonyms Sources
(±)-secobarbital DrugBank
5-(1-methylbutyl)-5-(2-propenyl)-2,4,6(1H,3H,5H)-pyrimidinetrione ChemIDplus
5-allyl-5-(1-methylbutyl)-2,4,6(1H,3H,5H)-pyrimidinetrione NIST Chemistry WebBook
5-allyl-5-(1-methylbutyl)barbituric acid NIST Chemistry WebBook
5-allyl-5-(1-methylbutyl)pyrimidine-2,4,6(1H,3H,5H)-trione IUPAC
quinalbarbitone ChEBI
secobarbital NIST Chemistry WebBook
secobarbitone ChemIDplus
Seconal ChemIDplus
Database Links Databases
2428 DrugCentral
D00430 KEGG DRUG
DB00418 DrugBank
HMDB0014562 HMDB
Secobarbital Wikipedia
View more database links
Registry Numbers Types Sources
225330 Reaxys Registry Number Reaxys
225330 Beilstein Registry Number Beilstein
283703 Gmelin Registry Number Gmelin
76-73-3 CAS Registry Number NIST Chemistry WebBook
76-73-3 CAS Registry Number ChemIDplus
Last Modified
22 February 2017
General Comment
2010-12-13 Secobarbital is a barbiturate derivative drug possessing anaesthetic, anticonvulsant, sedative and hypnotic properties. Formerly used as the sodium salt as a hypnotic for the short-term management of insomnia and as premedication in anaesthetic procedures, it has been largely replaced by other drugs.