CHEBI:584020 - methysergide

ChEBI IDCHEBI:584020
ChEBI Namemethysergide
Stars
DefinitionA 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.
Secondary ChEBI IDCHEBI:6893
Last Modified28 July 2014
DownloadsMolfile
FormulaC21H27N3O2
Net Charge0
Average Mass353.466
Monoisotopic Mass353.21033
SMILES[H][C@@]12Cc3cn(C)c4cccc(c34)C1=C[C@@H](C(=O)NC(CC)CO)CN2C
InChIInChI=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
InChIKeyKPJZHOPZRAFDTN-NQUBZZJWSA-N
Roles Classification
Biological Roles:
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.
Applications:
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.
ChEBI Ontology
Outgoing Relation(s)
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  Source
methysergideChEBI
méthysergideChEBI
methysergidumChEBI
metisergidaChEBI
Synonyms  Source
MethysergideKEGG COMPOUND
(+)-9,10-Didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8β-carboxamideChemIDplus
(+)-N-(1-(Hydroxymethyl)propyl)-1-methyl-D-lysergamideChemIDplus
1-Methyl-D-lysergic acid butanolamideChemIDplus
1-Methyl-dextro-lysergic acid (+)-1-hydroxy-2-butylamideChemIDplus
1-Methyllysergic acid butanolamideChemIDplus
Manual XrefsDatabases
C07199KEGG COMPOUND
D02357KEGG DRUG
DB00247DrugBank
GB854569Patent
US3113133Patent
Registry NumbersSources
Beilstein:765986Beilstein
CAS:361-37-5ChemIDplus