CHEBI:64203 - methiothepin

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ChEBI Name methiothepin
ChEBI ID CHEBI:64203
Definition A dibenzothiepine that is 10,11-dihydrodibenzo[b,f]thiepine bearing additional methylthio and 4-methylpiperazin-1-yl substituents at positions 8 and 10 respectively. Potent 5-HT2 antagonist, also active as 5-HT1 antagonist. Differentiates 5-HT1D sub-types. Also displays affinity for rodent 5-HT5B, 5-HT5A, 5-HT7 and 5-HT6 receptors (pK1 values are 6.6, 7.0, 8.4 and 8.7 respectively).
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H24N2S2
Net Charge 0
Average Mass 356.54800
Monoisotopic Mass 356.138
InChI InChI=1S/C20H24N2S2/c1-21-9-11-22(12-10-21)18-13-15-5-3-4-6-19(15)24-20-8-7-16(23-2)14-17(18)20/h3-8,14,18H,9-13H2,1-2H3
InChIKey RLJFTICUTYVZDG-UHFFFAOYSA-N
SMILES CSc1ccc2Sc3ccccc3CC(N3CCN(C)CC3)c2c1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): dopaminergic antagonist
A drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous agonists.
serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
Application(s): antipsychotic agent
Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect.
dopaminergic antagonist
A drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous agonists.
serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
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ChEBI Ontology
Outgoing methiothepin (CHEBI:64203) has role antipsychotic agent (CHEBI:35476)
methiothepin (CHEBI:64203) has role dopaminergic antagonist (CHEBI:48561)
methiothepin (CHEBI:64203) has role serotonergic antagonist (CHEBI:48279)
methiothepin (CHEBI:64203) is a N-alkylpiperazine (CHEBI:46845)
methiothepin (CHEBI:64203) is a aryl sulfide (CHEBI:35683)
methiothepin (CHEBI:64203) is a dibenzothiepine (CHEBI:38924)
methiothepin (CHEBI:64203) is a tertiary amino compound (CHEBI:50996)
methiothepin (CHEBI:64203) is conjugate base of methiothepin(2+) (CHEBI:64204)
Incoming methiothepin(2+) (CHEBI:64204) is conjugate acid of methiothepin (CHEBI:64203)
IUPAC Name
1-methyl-4-[8-(methylsulfanyl)-10,11-dihydrodibenzo[b,f]thiepin-10-yl]piperazine
INNs Sources
metitepina ChemIDplus
metitepine ChemIDplus
metitepinum ChemIDplus
Synonyms Sources
(+-)-1-(10,11-Dihydro-8-(methylthio)dibenzo(b,f)thiepin-10-yl)-4-methylpiperazine ChemIDplus
(+-)-10-(4-Methylpiperazinyl)-8-(methylthio)-10,11-dihydrodibenzo(b,f)thiepin ChemIDplus
(+-)-8-Methylthio-10-(4-methylpiperazino)-10,11-dihydrodibenzo(b,f)thiepin ChemIDplus
1-(10,11-Dihydro-8-(methylthio)dibenzo(b,f)thiepin-10-yl)-4-methylpiperazine ChemIDplus
1-methyl-4-[8-(methylthio)-10,11-dihydrodibenzo[b,f]thiepin-10-yl]piperazine ChEBI
Methiothepine ChemIDplus
Manual Xrefs Databases
LSM-4320 LINCS
Metitepine Wikipedia
NL6608618 Patent
US3379729 Patent
US4444778 Patent
US6331536 Patent
View more database links
Registry Numbers Types Sources
20229-30-5 CAS Registry Number ChemIDplus
626221 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
18996971 PubMed citation Europe PMC
19837141 PubMed citation Europe PMC
19995401 PubMed citation Europe PMC
20171242 PubMed citation Europe PMC
20233210 PubMed citation Europe PMC
20331882 PubMed citation Europe PMC
20547148 PubMed citation Europe PMC
21062995 PubMed citation Europe PMC
21403818 PubMed citation Europe PMC
21514998 PubMed citation Europe PMC
21964383 PubMed citation Europe PMC
Last Modified
25 February 2016