CHEBI:6838 - methotrimeprazine

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ChEBI Name methotrimeprazine
ChEBI ID CHEBI:6838
Definition A member of the class of phenothiazines that is 10H-phenothiazine substituted by a (2R)-3-(dimethylamino)-2-methylpropyl group and a methoxy group at positions 10 and 2 respectively.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C19H24N2OS
Net Charge 0
Average Mass 328.47274
Monoisotopic Mass 328.161
InChI InChI=1S/C19H24N2OS/c1-14(12-20(2)3)13-21-16-7-5-6-8-18(16)23-19-10-9-15(22-4)11-17(19)21/h5-11,14H,12-13H2,1-4H3/t14-/m1/s1
InChIKey VRQVVMDWGGWHTJ-CQSZACIVSA-N
SMILES COc1ccc2Sc3ccccc3N(C[C@H](C)CN(C)C)c2c1
Roles Classification
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.
cholinergic antagonist
Any drug that binds to but does not activate cholinergic receptors, thereby blocking the actions of acetylcholine or cholinergic agonists.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
Any EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of prolyl oligopeptidase (EC 3.4.21.26).
Application(s): phenothiazine antipsychotic drug

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.
cholinergic antagonist
Any drug that binds to but does not activate cholinergic receptors, thereby blocking the actions of acetylcholine or cholinergic agonists.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
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ChEBI Ontology
Outgoing methotrimeprazine (CHEBI:6838) has parent hydride 10H-phenothiazine (CHEBI:37931)
methotrimeprazine (CHEBI:6838) has role cholinergic antagonist (CHEBI:48873)
methotrimeprazine (CHEBI:6838) has role dopaminergic antagonist (CHEBI:48561)
methotrimeprazine (CHEBI:6838) has role EC 3.4.21.26 (prolyl oligopeptidase) inhibitor (CHEBI:76779)
methotrimeprazine (CHEBI:6838) has role non-narcotic analgesic (CHEBI:35481)
methotrimeprazine (CHEBI:6838) has role phenothiazine antipsychotic drug (CHEBI:37930)
methotrimeprazine (CHEBI:6838) has role serotonergic antagonist (CHEBI:48279)
methotrimeprazine (CHEBI:6838) is a phenothiazines (CHEBI:38093)
methotrimeprazine (CHEBI:6838) is a tertiary amine (CHEBI:32876)
IUPAC Name
(2R)-3-(2-methoxy-10H-phenothiazin-10-yl)-N,N,2-trimethylpropan-1-amine
INNs Sources
levomepromazina ChEBI
lévomépromazine ChEBI
levomepromazine WHO MedNet
levomepromazinum ChEBI
Synonyms Sources
(-)-(2R)-3-(2-methoxy-10H-phenothiazin-10-yl)-N,N,2-trimethylpropan-1-amine ChemIDplus
(-)-10-(3-(Dimethylamino)-2-methylpropyl)-2-methoxyphenothiazine ChemIDplus
2-Methoxytrimeprazine ChemIDplus
Levomepromazine KEGG COMPOUND
Methotrimeprazine KEGG COMPOUND
Database Links Databases
1752 DrugCentral
C07192 KEGG COMPOUND
D00403 KEGG DRUG
D06474 KEGG DRUG
DB01403 DrugBank
HMDB0015474 HMDB
Levomepromazine Wikipedia
LSM-2778 LINCS
US2837518 Patent
View more database links
Registry Numbers Types Sources
60-99-1 CAS Registry Number ChemIDplus
60-99-1 CAS Registry Number NIST Chemistry WebBook
92434 Reaxys Registry Number Reaxys
92434 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
11026079 PubMed citation Europe PMC
11260766 PubMed citation Europe PMC
15700129 PubMed citation Europe PMC
20825390 PubMed citation Europe PMC
Last Modified
22 February 2017