CHEBI:584020 - methysergide

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ChEBI Name methysergide
ChEBI ID CHEBI:584020
Definition A synthetic ergot alkaloid, structurally related to the oxytocic agent methylergonovine and to the potent hallucinogen LSD and used prophylactically to reduce the frequency and intensity of severe vascular headaches.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:6893
Supplier Information
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Formula C21H27N3O2
Net Charge 0
Average Mass 353.45810
Monoisotopic Mass 353.21033
InChI InChI=1S/C21H27N3O2/c1-4-15(12-25)22-21(26)14-8-17-16-6-5-7-18-20(16)13(10-23(18)2)9-19(17)24(3)11-14/h5-8,10,14-15,19,25H,4,9,11-12H2,1-3H3,(H,22,26)/t14-,15?,19-/m1/s1
InChIKey KPJZHOPZRAFDTN-NQUBZZJWSA-N
SMILES [H][C@@]12Cc3cn(C)c4cccc(C1=C[C@H](CN2C)C(=O)NC(CC)CO)c34
Roles Classification
Biological Role(s): sympatholytic agent
Any compound which inhibits the postganglionic functioning of the sympathetic nervous system (SNS).
serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): sympatholytic agent
Any compound which inhibits the postganglionic functioning of the sympathetic nervous system (SNS).
vasoconstrictor agent
Drug used to cause constriction of the blood vessels.
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 methysergide (CHEBI:584020) has parent hydride ergoline (CHEBI:38484)
methysergide (CHEBI:584020) has role serotonergic antagonist (CHEBI:48279)
methysergide (CHEBI:584020) has role sympatholytic agent (CHEBI:66991)
methysergide (CHEBI:584020) has role vasoconstrictor agent (CHEBI:50514)
methysergide (CHEBI:584020) is a ergot alkaloid (CHEBI:23943)
methysergide (CHEBI:584020) is a monocarboxylic acid amide (CHEBI:29347)
IUPAC Name
(8R)-N-[1-hydroxymethyl(propyl)]-1,6-dimethyl-9,10-didehydroergoline-8-carboxamide
INNs Sources
méthysergide ChEBI
methysergide ChEBI
methysergidum ChEBI
metisergida ChEBI
Synonyms Sources
(+)-9,10-Didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8β-carboxamide ChemIDplus
(+)-N-(1-(Hydroxymethyl)propyl)-1-methyl-D-lysergamide ChemIDplus
1-Methyl-D-lysergic acid butanolamide ChemIDplus
1-Methyl-dextro-lysergic acid (+)-1-hydroxy-2-butylamide ChemIDplus
1-Methyllysergic acid butanolamide ChemIDplus
1-Methylmethylergonovine ChemIDplus
9,10-Didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8-carboxamide ChemIDplus
Methysergide KEGG COMPOUND
N-(1-(Hydroxymethyl)propyl)-1-methyl-dextro-(+)-lysergamide ChemIDplus
Manual Xrefs Databases
C07199 KEGG COMPOUND
D02357 KEGG DRUG
DB00247 DrugBank
GB854569 Patent
US3113133 Patent
View more database links
Registry Numbers Types Sources
361-37-5 CAS Registry Number ChemIDplus
765986 Beilstein Registry Number Beilstein
Last Modified
28 July 2014