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CHEBI:64216 - metergoline

Default Structure
ChEBI IDCHEBI:64216
ChEBI Namemetergoline
Stars
DefinitionAn ergoline alkaloid that is the N-benzyloxycarbonyl derivative of lysergamine. A 5-HT2 antagonist. Also 5-HT1 antagonist and 5-HT1D ligand. Has moderate affinity for 5-HT6 and high affinity for 5-HT7.
Last Modified26 October 2021
SubmitterSteve
DownloadsMolfile
FormulaC25H29N3O2
Net Charge0
Average Mass403.526
Monoisotopic Mass403.22598
SMILES[H][C@@]12Cc3cn(C)c4cccc(c34)[C@@]1([H])C[C@@H](CNC(=O)OCc1ccccc1)CN2C
InChIInChI=1S/C25H29N3O2/c1-27-14-18(13-26-25(29)30-16-17-7-4-3-5-8-17)11-21-20-9-6-10-22-24(20)19(12-23(21)27)15-28(22)2/h3-10,15,18,21,23H,11-14,16H2,1-2H3,(H,26,29)/t18-,21+,23+/m0/s1
InChIKeyWZHJKEUHNJHDLS-QTGUNEKASA-N
Wikipedia
Roles Classification
Biological Roles:
dopamine agonist  A drug that binds to and activates dopamine receptors.
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:
dopamine agonist  A drug that binds to and activates dopamine receptors.
geroprotector  Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
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)
metergoline (CHEBI:64216) has role dopamine agonist (CHEBI:51065)
metergoline (CHEBI:64216) has role geroprotector (CHEBI:176497)
metergoline (CHEBI:64216) has role serotonergic antagonist (CHEBI:48279)
metergoline (CHEBI:64216) is a carbamate ester (CHEBI:23003)
metergoline (CHEBI:64216) is a ergoline alkaloid (CHEBI:60529)
IUPAC Name 
benzyl {[(8α)-1,6-dimethylergolin-8-yl]methyl}carbamate
INNs  Source
metergolinaChemIDplus
metergolineKEGG DRUG
metergolinumChemIDplus
Synonyms  Source
1,6-Dimethyl-8-beta-carbobenzyloxaminomethyl-10-alpha-ergolineChemIDplus
1-Methyl-8-beta-carbobenzyloxyaminomethyl-10-alpha-ergolineChemIDplus
1-Methyl-N-carbobenzyloxydihydro-D-lysergaminChemIDplus
(((8-beta)-1,6-Dimethylergolin-8-yl)methyl)carbamic acid benzyl esterChemIDplus
(((8-beta)-1,6-Dimethylergolin-8-yl)methyl)carbamic acid phenylmethyl esterChemIDplus
D-8-beta-((Carbobenzoxyamino)methyl)-1,6-dimethyl-10-alpha-ergolineChemIDplus
Manual XrefsDatabases
1723DrugCentral
D07218KEGG DRUG
LSM-3265LINCS
MetergolineWikipedia
Registry NumbersSources
Reaxys:5362415Reaxys
CAS:17692-51-2NIST Chemistry WebBook
CAS:17692-51-2KEGG DRUG
CAS:17692-51-2ChemIDplus
Citations