CHEBI:102166 - thiopental

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ChEBI Name thiopental
ChEBI ID CHEBI:102166
Definition A barbiturate, the structure of which is that of 2-thiobarbituric acid substituted at C-5 by ethyl and sec-pentyl groups.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:9560
Supplier Information
Download Molfile XML SDF
Formula C11H18N2O2S
Net Charge 0
Average Mass 242.33800
Monoisotopic Mass 242.109
InChI InChI=1S/C11H18N2O2S/c1-4-6-7(3)11(5-2)8(14)12-10(16)13-9(11)15/h7H,4-6H2,1-3H3,(H2,12,13,14,15,16)
InChIKey IUJDSEJGGMCXSG-UHFFFAOYSA-N
SMILES CCCC(C)C1(CC)C(=O)NC(=S)NC1=O
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): drug allergen
Any drug which causes the onset of an allergic reaction.
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
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): drug allergen
Any drug which causes the onset of an allergic reaction.
anticonvulsant
A drug used to prevent seizures or reduce their severity.
sedative
A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
intravenous anaesthetic

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 thiopental (CHEBI:102166) has functional parent 2-thiobarbituric acid (CHEBI:33202)
thiopental (CHEBI:102166) has role anticonvulsant (CHEBI:35623)
thiopental (CHEBI:102166) has role drug allergen (CHEBI:88188)
thiopental (CHEBI:102166) has role environmental contaminant (CHEBI:78298)
thiopental (CHEBI:102166) has role intravenous anaesthetic (CHEBI:38877)
thiopental (CHEBI:102166) has role sedative (CHEBI:35717)
thiopental (CHEBI:102166) has role xenobiotic (CHEBI:35703)
thiopental (CHEBI:102166) is a barbiturates (CHEBI:22693)
thiopental (CHEBI:102166) is conjugate acid of thiopental(1−) (CHEBI:61485)
Incoming thiopental(1−) (CHEBI:61485) is conjugate base of thiopental (CHEBI:102166)
IUPAC Name
5-ethyl-5-(pentan-2-yl)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
Synonyms Sources
(±)-thiopental ChemIDplus
2-Thio-5-ethyl-5-sec-pentylbarbituric acid ChemIDplus
5-Ethyl-5-(1-methyl-butyl)-2-thioxo-dihydro-pyrimidine-4,6-dione ChEMBL
Penthiobarbital ChemIDplus
Pentothiobarbital ChemIDplus
Thiopental KEGG COMPOUND
Thiopentobarbital ChemIDplus
Thiopentobarbitone ChemIDplus
Thiopentobarbituric acid ChemIDplus
Thiopentone ChemIDplus
Database Links Databases
2633 DrugCentral
C07521 KEGG COMPOUND
DB00599 DrugBank
View more database links
Registry Numbers Types Sources
209361 Beilstein Registry Number Beilstein
209361 Reaxys Registry Number Reaxys
76-75-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10666006 PubMed citation Europe PMC
10841799 PubMed citation ChEMBL
15857133 PubMed citation ChEMBL
16166909 PubMed citation Europe PMC
16897573 PubMed citation Europe PMC
18484074 PubMed citation Europe PMC
20488867 PubMed citation Europe PMC
2215478 PubMed citation Europe PMC
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23422796 PubMed citation Europe PMC
23490495 PubMed citation Europe PMC
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23644730 PubMed citation Europe PMC
23879844 PubMed citation Europe PMC
3654008 PubMed citation Europe PMC
6864729 PubMed citation ChEMBL
9171876 PubMed citation ChEMBL
9699097 PubMed citation Europe PMC
Last Modified
22 February 2017