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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:
serotonergic antagonist  Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
dopamine agonist  A drug that binds to and activates dopamine receptors.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
serotonergic antagonist  Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
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.
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:17692-51-2ChemIDplus
CAS:17692-51-2KEGG DRUG
Citations