Mesulergine (CHEM018925)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:40:40 UTC
Update Date2026-04-15 17:52:35 UTC
Accession NumberCHEM018925
Identification
Common NameMesulergine
ClassSmall Molecule
DescriptionA member of the class of ergot alkaloids that is known to act on serotonin and dopamine receptors.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
MesulerginaChEBI
MesulerginumChEBI
N'-(1,6-dimethylergolin-8alpha-yl)-N,N-dimethylsulfamideChEBI
N'-(1,6-dimethylergolin-8a-yl)-N,N-dimethylsulfamideGenerator
N'-(1,6-dimethylergolin-8a-yl)-N,N-dimethylsulphamideGenerator
N'-(1,6-dimethylergolin-8alpha-yl)-N,N-dimethylsulphamideGenerator
N'-(1,6-dimethylergolin-8α-yl)-N,N-dimethylsulfamideGenerator
N'-(1,6-dimethylergolin-8α-yl)-N,N-dimethylsulphamideGenerator
(6Ar,9S,10ar)-9-(dimethylsulphamoylamino)-4,7-dimethyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-FG]quinolineGenerator
MesulergineMeSH
Mesulergine monohydrochlorideMeSH
Chemical FormulaC18H26N4O2S
Average Molecular Mass362.490 g/mol
Monoisotopic Mass362.178 g/mol
CAS Registry Number64795-35-3
IUPAC Name{[(2R,4S,7R)-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraen-4-yl]sulfamoyl}dimethylamine
Traditional Namemesulergine
SMILES[H][C@]1(CN(C)[C@]2([H])CC3=CN(C)C4=CC=CC(=C34)[C@@]2([H])C1)NS(=O)(=O)N(C)C
InChI IdentifierInChI=1S/C18H26N4O2S/c1-20(2)25(23,24)19-13-9-15-14-6-5-7-16-18(14)12(10-21(16)3)8-17(15)22(4)11-13/h5-7,10,13,15,17,19H,8-9,11H2,1-4H3/t13-,15+,17+/m0/s1
InChI KeyJLVHTNZNKOSCNB-YSVLISHTSA-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
  • N-alkylindole
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Isoindole or derivatives
  • Alkaloid or derivatives
  • Aralkylamine
  • N-methylpyrrole
  • Sulfuric acid diamide
  • Piperidine
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Organic sulfuric acid or derivatives
  • Heteroaromatic compound
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organopnictogen compound
  • 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 Solubility0.87 g/LALOGPS
logP1.56ALOGPS
logP1.08ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)11.08ChemAxon
pKa (Strongest Basic)6.9ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.58 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity100.29 m³·mol⁻¹ChemAxon
Polarizability39.8 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dr-0059000000-49ba69010f7f0bfceb5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190000000-eb966c5e5307780af037Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03yl-0940000000-06a4c29a2a7f5a601d3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0209000000-1f93f5bfb09f5d22b6baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0909-2449000000-46e1ef51991198c1162fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ox-9310000000-0bd6910491c92724cd89Spectrum
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 IDNot Available
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 LinkMesulergine
Chemspider IDNot Available
ChEBI ID73378
PubChem Compound ID68848
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=21190911
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22313641
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23597562
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=2895480
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=3428838
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=3708600
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=3881692
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=3895033
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=4067602
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=6230246
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=6386276
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=6488683
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=6527137