CHEBI:64216 - metergoline

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
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.
Supplier Information
Download Molfile XML SDF
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C25H29N3O2
Net Charge 0
Average Mass 403.51670
Monoisotopic Mass 403.226
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing metergoline (CHEBI:64216) has role dopamine agonist (CHEBI:51065)
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
Database Links 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
19484723 PubMed citation Europe PMC
19509219 PubMed citation Europe PMC
19538518 PubMed citation Europe PMC
19539656 PubMed citation Europe PMC
19632276 PubMed citation Europe PMC
19945477 PubMed citation Europe PMC
20377624 PubMed citation Europe PMC
20451398 PubMed citation Europe PMC
20845263 PubMed citation Europe PMC
21354537 PubMed citation Europe PMC
21475142 PubMed citation Europe PMC
21600959 PubMed citation Europe PMC
21880033 PubMed citation Europe PMC
22218419 PubMed citation Europe PMC
Last Modified
22 February 2017