EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:9536 - thiamylal

ChEBI IDCHEBI:9536
ChEBI Namethiamylal
Stars
DefinitionA 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.
Last Modified22 February 2017
DownloadsMolfile
FormulaC12H18N2O2S
Net Charge0
Average Mass254.355
Monoisotopic Mass254.10890
SMILESC=CCC1(C(C)CCC)C(=O)NC(=S)NC1=O
InChIInChI=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)
InChIKeyXLOMZPUITCYLMJ-UHFFFAOYSA-N
Wikipedia
Roles Classification
Biological Role:
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.
Applications:
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.
ChEBI Ontology
Outgoing Relation(s)
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  Source
5-Allyl-5-(1-methylbutyl)-2-thiobarbituric acidKEGG COMPOUND
5-allyl-5-(1-methylbutyl)-2-thioxodihydro-4,6(1H,5H)-pyrimidinedioneNIST Chemistry WebBook
5-allyl-5-(1-methylbutyl)-2-thioxodihydropyrimidine-4,6(1H,5H)-dioneIUPAC
dihydro-5-(1-methylbutyl)-5-(2-propenyl)-2-thioxo-4,6(1H,5H)-pyrimidinedioneNIST Chemistry WebBook
ThiamylalKEGG COMPOUND
thioseconalChemIDplus
Manual XrefsDatabases
2626DrugCentral
C07846KEGG COMPOUND
D06106KEGG DRUG
DB01154DrugBank
HMDB0015285HMDB
LSM-4367LINCS
ThiamylalWikipedia
Registry NumbersSources
Reaxys:225331Reaxys
CAS:77-27-0KEGG COMPOUND
CAS:77-27-0NIST Chemistry WebBook
CAS:77-27-0ChemIDplus
Citations