CHEBI:64216 - metergoline

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ChEBI Name metergoline
ChEBI ID CHEBI:64216
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C25H29N3O2
Net Charge 0
Average Mass 403.51670
Monoisotopic Mass 403.22598
InChI InChI=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
InChIKey WZHJKEUHNJHDLS-QTGUNEKASA-N
SMILES [H][C@@]12Cc3cn(C)c4cccc(c34)[C@@]1([H])C[C@@H](CNC(=O)OCc1ccccc1)CN2C
Roles Classification
Biological Role(s): 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.
(via alkaloid )
Application(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
metergolina ChemIDplus
metergoline KEGG DRUG
metergolinum ChemIDplus
Synonyms Sources
(((8-beta)-1,6-Dimethylergolin-8-yl)methyl)carbamic acid benzyl ester ChemIDplus
(((8-beta)-1,6-Dimethylergolin-8-yl)methyl)carbamic acid phenylmethyl ester ChemIDplus
(+)-N-(Carboxy)-1-methyl-9,10-dihydrolysergamine benzyl ester ChemIDplus
1,6-Dimethyl-8-beta-carbobenzyloxaminomethyl-10-alpha-ergoline ChemIDplus
1-Methyl-8-beta-carbobenzyloxyaminomethyl-10-alpha-ergoline ChemIDplus
1-Methyl-N-carbobenzyloxydihydro-D-lysergamin ChemIDplus
D-8-beta-((Carbobenzoxyamino)methyl)-1,6-dimethyl-10-alpha-ergoline ChemIDplus
D-8-beta-((Carboxyamino)methyl)-1,6-dimethylergoline benzyl ester ChemIDplus
Metergolin ChemIDplus
Manual Xrefs Databases
1723 DrugCentral
D07218 KEGG DRUG
LSM-3265 LINCS
Metergoline Wikipedia
View more database links
Registry Numbers Types Sources
17692-51-2 CAS Registry Number ChemIDplus
17692-51-2 CAS Registry Number KEGG DRUG
17692-51-2 CAS Registry Number NIST Chemistry WebBook
5362415 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
18996971 PubMed citation Europe PMC
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Last Modified
26 October 2021