CHEBI:6758 - mephobarbital

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ChEBI Name mephobarbital
ChEBI ID CHEBI:6758
Definition A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at N-1 by a methyl group and at C-5 by ethyl and phenyl groups.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:165567
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Formula C13H14N2O3
Net Charge 0
Average Mass 246.26190
Monoisotopic Mass 246.100
InChI InChI=1S/C13H14N2O3/c1-3-13(9-7-5-4-6-8-9)10(16)14-12(18)15(2)11(13)17/h4-8H,3H2,1-2H3,(H,14,16,18)
InChIKey ALARQZQTBTVLJV-UHFFFAOYSA-N
SMILES CCC1(C(=O)NC(=O)N(C)C1=O)c1ccccc1
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): anticonvulsant
A drug used to prevent seizures or reduce their severity.
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 )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing mephobarbital (CHEBI:6758) has role anticonvulsant (CHEBI:35623)
mephobarbital (CHEBI:6758) is a barbiturates (CHEBI:22693)
IUPAC Name
5-ethyl-1-methyl-5-phenylpyrimidine-2,4,6(1H,3H,5H)-trione
INNs Sources
methylphenobarbital KEGG DRUG
methylphenobarbitalum DrugBank
metilfenobarbital DrugBank
Synonyms Sources
1-methylphenobarbital NIST Chemistry WebBook
5-ethyl-1-methyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione NIST Chemistry WebBook
5-Ethyl-1-methyl-5-phenyl-pyrimidine-2,4,6-trione ChEMBL
5-ethyl-1-methyl-5-phenylbarbituric acid NIST Chemistry WebBook
Mebaral ChemIDplus
Mephobarbital KEGG COMPOUND
Mephobarbitone ChemIDplus
methylphenobarbital ChEBI
N-methylphenobarbital NIST Chemistry WebBook
Manual Xrefs Databases
1696 DrugCentral
C07829 KEGG COMPOUND
D00700 KEGG DRUG
DB00849 DrugBank
HMDB0014987 HMDB
Methylphenobarbital Wikipedia
View more database links
Registry Numbers Types Sources
115-38-8 CAS Registry Number KEGG COMPOUND
115-38-8 CAS Registry Number ChemIDplus
115-38-8 CAS Registry Number NIST Chemistry WebBook
256144 Reaxys Registry Number Reaxys
256144 Beilstein Registry Number Beilstein
282754 Gmelin Registry Number Gmelin
Citations Waiting for Citations Types Sources
12873507 PubMed citation ChEMBL
1455071 PubMed citation Europe PMC
2083148 PubMed citation Europe PMC
22342565 PubMed citation Europe PMC
2249375 PubMed citation Europe PMC
3298402 PubMed citation Europe PMC
3654008 PubMed citation Europe PMC
553327 PubMed citation Europe PMC
6094812 PubMed citation ChEMBL
Last Modified
22 February 2017
General Comment
2014-05-08 Mephobarbital can be found in blood and urine samples of individuals who have taken this drug.