CHEBI:9536 - thiamylal

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ChEBI Name thiamylal
ChEBI ID CHEBI:9536
Definition A member of the class of barbiturates that is 2-thioxodihydropyrimidine-4,6(1H,5H)-dione substituted by a pentan-2-yl and prop-2-en-1-yl group at position 5.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information No supplier information found for this compound.
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Formula C12H18N2O2S
Net Charge 0
Average Mass 254.34960
Monoisotopic Mass 254.10890
InChI InChI=1S/C12H18N2O2S/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 XLOMZPUITCYLMJ-UHFFFAOYSA-N
SMILES CCCC(C)C1(CC=C)C(=O)NC(=S)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): sedative
A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
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 thiamylal (CHEBI:9536) has role sedative (CHEBI:35717)
thiamylal (CHEBI:9536) is a barbiturates (CHEBI:22693)
thiamylal (CHEBI:9536) is a organosulfur compound (CHEBI:33261)
IUPAC Name
5-(pentan-2-yl)-5-(prop-2-en-1-yl)-2-sulfanylidenedihydropyrimidine-4,6(1H,5H)-dione
Synonyms Sources
5-Allyl-5-(1-methylbutyl)-2-thiobarbituric acid KEGG COMPOUND
5-allyl-5-(1-methylbutyl)-2-thioxodihydro-4,6(1H,5H)-pyrimidinedione NIST Chemistry WebBook
5-allyl-5-(1-methylbutyl)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione IUPAC
dihydro-5-(1-methylbutyl)-5-(2-propenyl)-2-thioxo-4,6(1H,5H)-pyrimidinedione NIST Chemistry WebBook
Thiamylal KEGG COMPOUND
thioseconal ChemIDplus
Manual Xrefs Databases
2626 DrugCentral
C07846 KEGG COMPOUND
D06106 KEGG DRUG
DB01154 DrugBank
HMDB0015285 HMDB
LSM-4367 LINCS
Thiamylal Wikipedia
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Registry Numbers Types Sources
225331 Reaxys Registry Number Reaxys
77-27-0 CAS Registry Number NIST Chemistry WebBook
77-27-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations
Last Modified
22 February 2017