Metergoline (CHEM017834)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:41:00 UTC
Update Date2016-11-09 01:15:40 UTC
Accession NumberCHEM017834
Identification
Common NameMetergoline
ClassSmall Molecule
DescriptionAn 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.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(((8-beta)-1,6-Dimethylergolin-8-yl)methyl)carbamic acid benzyl esterChEBI
(((8-beta)-1,6-Dimethylergolin-8-yl)methyl)carbamic acid phenylmethyl esterChEBI
(+)-N-(Carboxy)-1-methyl-9,10-dihydrolysergamine benzyl esterChEBI
1,6-Dimethyl-8-beta-carbobenzyloxaminomethyl-10-alpha-ergolineChEBI
1-Methyl-8-beta-carbobenzyloxyaminomethyl-10-alpha-ergolineChEBI
1-Methyl-N-carbobenzyloxydihydro-D-lysergaminChEBI
D-8-beta-((Carbobenzoxyamino)methyl)-1,6-dimethyl-10-alpha-ergolineChEBI
D-8-beta-((Carboxyamino)methyl)-1,6-dimethylergoline benzyl esterChEBI
MetergolinChEBI
MetergolinaChEBI
MetergolinumChEBI
(((8-b)-1,6-Dimethylergolin-8-yl)methyl)carbamate benzyl esterGenerator
(((8-b)-1,6-Dimethylergolin-8-yl)methyl)carbamic acid benzyl esterGenerator
(((8-beta)-1,6-Dimethylergolin-8-yl)methyl)carbamate benzyl esterGenerator
(((8-Β)-1,6-dimethylergolin-8-yl)methyl)carbamate benzyl esterGenerator
(((8-Β)-1,6-dimethylergolin-8-yl)methyl)carbamic acid benzyl esterGenerator
(((8-b)-1,6-Dimethylergolin-8-yl)methyl)carbamate phenylmethyl esterGenerator
(((8-b)-1,6-Dimethylergolin-8-yl)methyl)carbamic acid phenylmethyl esterGenerator
(((8-beta)-1,6-Dimethylergolin-8-yl)methyl)carbamate phenylmethyl esterGenerator
(((8-Β)-1,6-dimethylergolin-8-yl)methyl)carbamate phenylmethyl esterGenerator
(((8-Β)-1,6-dimethylergolin-8-yl)methyl)carbamic acid phenylmethyl esterGenerator
1,6-Dimethyl-8-b-carbobenzyloxaminomethyl-10-a-ergolineGenerator
1,6-Dimethyl-8-β-carbobenzyloxaminomethyl-10-α-ergolineGenerator
1-Methyl-8-b-carbobenzyloxyaminomethyl-10-a-ergolineGenerator
1-Methyl-8-β-carbobenzyloxyaminomethyl-10-α-ergolineGenerator
D-8-b-((Carbobenzoxyamino)methyl)-1,6-dimethyl-10-a-ergolineGenerator
D-8-Β-((carbobenzoxyamino)methyl)-1,6-dimethyl-10-α-ergolineGenerator
D-8-b-((Carboxyamino)methyl)-1,6-dimethylergoline benzyl esterGenerator
D-8-Β-((carboxyamino)methyl)-1,6-dimethylergoline benzyl esterGenerator
Metergoline teofarma brandMeSH
LiserdolMeSH
MethergolineMeSH
Teofarma brand OF metergolineMeSH
Chemical FormulaC25H29N3O2
Average Molecular Mass403.526 g/mol
Monoisotopic Mass403.226 g/mol
CAS Registry Number17692-51-2
IUPAC NameN-{[(2R,4R,7R)-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraen-4-yl]methyl}(benzyloxy)carboximidic acid
Traditional Namemethergoline
SMILES[H][C@]1(CN=C(O)OCC2=CC=CC=C2)CN(C)[C@]2([H])CC3=CN(C)C4=CC=CC(=C34)[C@@]2([H])C1
InChI IdentifierInChI=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
InChI KeyWZHJKEUHNJHDLS-QTGUNEKASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as indoloquinolines. These are polycyclic aromatic compounds containing an indole fused to a quinoline.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassIndoloquinolines
Direct ParentIndoloquinolines
Alternative Parents
Substituents
  • Ergoline skeleton
  • Indoloquinoline
  • Benzoquinoline
  • Pyrroloquinoline
  • Benzyloxycarbonyl
  • N-alkylindole
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Isoindole or derivatives
  • Alkaloid or derivatives
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • N-methylpyrrole
  • Substituted pyrrole
  • Piperidine
  • Heteroaromatic compound
  • Carbamic acid ester
  • Pyrrole
  • Carbonic acid derivative
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Organonitrogen compound
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP3.99ALOGPS
logP2.04ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)4.35ChemAxon
pKa (Strongest Basic)8.69ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.99 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity120.09 m³·mol⁻¹ChemAxon
Polarizability47.33 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0ir0-4794200000-d04091d908ab86f9807eSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0ir0-4794200000-d04091d908ab86f9807eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0191300000-4835b4de6449fef92facSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fr6-3190000000-0d779d001d5c1019b1e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bi-1490000000-2c9b03a38c2e1316c36bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1290200000-b57626c1f72345f0dc0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9370000000-56877b695eaa70a67a42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9470000000-a8cb594fb31952430f98Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB13520
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMetergoline
Chemspider IDNot Available
ChEBI ID64216
PubChem Compound ID28693
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=18996971
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19484723
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19509219
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19538518
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19539656
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=19632276
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=19945477
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=20377624
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=20451398
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=20845263
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=21354537
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=21475142
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=21600959
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=21880033
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22218419