thiamylal (CHEBI:9536)

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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.

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Formula

C12H18N2O2S

Net Charge

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 )

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

Last Modified

22 February 2017