Ergonovine (CHEM002654)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (10)XML
Record Information
Version1.0
Creation Date2010-04-21 17:59:34 UTC
Update Date2026-05-14 16:59:09 UTC
Accession NumberCHEM002654
Identification
Common NameErgonovine
ClassSmall Molecule
DescriptionErgonovine is only found in individuals that have used or taken this drug. It is an ergot alkaloid with uterine and vascular smooth muscle contractile properties. [PubChem] Ergonovine directly stimulates the uterine muscle to increase force and frequency of contractions. With usual doses, these contractions precede periods of relaxation; with larger doses, basal uterine tone is elevated and these relaxation periods will be decreased. Contraction of the uterine wall around bleeding vessels at the placental site produces hemostasis. Ergonovine also induces cervical contractions. The sensitivity of the uterus to the oxytocic effect is much greater toward the end of pregnancy. The oxytocic actions of ergonovine are greater than its vascular effects. Ergonovine, like other ergot alkaloids, produces arterial vasoconstriction by stimulation of alpha-adrenergic and serotonin receptors and inhibition of endothelial-derived relaxation factor release. It is a less potent vasoconstrictor than ergotamine. As a diagnostic aid (coronary vasospasm), ergonovine causes vasoconstriction of coronary arteries.
Contaminant Sources
  • DEA Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Drug
  • Fungal Toxin
  • Human Neurotoxin
  • Metabolite
  • Mycotoxin
  • Natural Compound
  • Organic Compound
  • Oxytocic
  • PFAS
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(6AR,9R)-7-methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-FG]quinoline-9-carboxylic acid ((S)-2-hydroxy-1-methyl-ethyl)-amideChEBI
9,10-Didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergoline-8beta(S)-carboxamideChEBI
9,10-Didehydro-N-(alpha-(hydroxymethyl)ethyl)-6-methylergoline-8-beta-carboxamideChEBI
[8beta(S)]-9,10-Didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergoline-8-carboxamideChEBI
D-Lysergic acid 1-hydroxymethylethylamideChEBI
D-Lysergic acid-L-propanolamideChEBI
ErgobasineChEBI
ErgometrinaChEBI
ErgometrinumChEBI
ErgotocineChEBI
MargonovineChEBI
N-(2-Hydroxy-1-methylethyl)-D-(+)-lysergamideChEBI
N-(alpha-(Hydroxymethyl)ethyl)-D-lysergamideChEBI
ErgometrineKegg
(6AR,9R)-7-methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-FG]quinoline-9-carboxylate ((S)-2-hydroxy-1-methyl-ethyl)-amideGenerator
9,10-Didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergoline-8b(S)-carboxamideGenerator
9,10-Didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergoline-8β(S)-carboxamideGenerator
9,10-Didehydro-N-(a-(hydroxymethyl)ethyl)-6-methylergoline-8-b-carboxamideGenerator
9,10-Didehydro-N-(α-(hydroxymethyl)ethyl)-6-methylergoline-8-β-carboxamideGenerator
[8b(S)]-9,10-Didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergoline-8-carboxamideGenerator
[8Β(S)]-9,10-didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergoline-8-carboxamideGenerator
D-Lysergate 1-hydroxymethylethylamideGenerator
D-Lysergate-L-propanolamideGenerator
N-(a-(Hydroxymethyl)ethyl)-D-lysergamideGenerator
N-(Α-(hydroxymethyl)ethyl)-D-lysergamideGenerator
Ergotrate maleateHMDB
Bedford brand OF ergonovine maleateHMDB
ErgobasinHMDB
ErgometrinHMDB
ErgotrateHMDB
Ergometrine maleateHMDB
Ergonovine maleateHMDB
ErgonovineChEBI
Chemical FormulaC19H23N3O2
Average Molecular Mass325.405 g/mol
Monoisotopic Mass325.179 g/mol
CAS Registry Number60-79-7
IUPAC Name(4R,7R)-N-[(2S)-1-hydroxypropan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
Traditional Nameergonovine
SMILES[H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@H](CN2C)C(=O)N[C@@H](C)CO
InChI IdentifierInChI=1S/C19H23N3O2/c1-11(10-23)21-19(24)13-6-15-14-4-3-5-16-18(14)12(8-20-16)7-17(15)22(2)9-13/h3-6,8,11,13,17,20,23H,7,9-10H2,1-2H3,(H,21,24)/t11-,13+,17+/m0/s1
InChI KeyWVVSZNPYNCNODU-XTQGRXLLSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as lysergamides. These are amides of Lysergic acids.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassErgoline and derivatives
Sub ClassLysergic acids and derivatives
Direct ParentLysergamides
Alternative Parents
Substituents
  • Lysergic acid amide
  • Indoloquinoline
  • Benzoquinoline
  • Pyrroloquinoline
  • Quinoline-3-carboxamide
  • Quinoline
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Isoindole or derivatives
  • Aralkylamine
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Amino acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Primary alcohol
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point162°C
Boiling PointNot Available
Solubility2.68 mg/mL at 25°C
Predicted Properties
PropertyValueSource
Water Solubility0.32 g/LALOGPS
logP1.53ALOGPS
logP1.07ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)15ChemAxon
pKa (Strongest Basic)7.93ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area68.36 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity95.05 m³·mol⁻¹ChemAxon
Polarizability36.54 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-3931000000-4bdb2fafa3f7edc31959Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006t-3941000000-efd4dcb7883cfc33a6d5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-1029000000-c07ebacb47f673bb1d1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kmi-2093000000-ac375307cfa93e46e2b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-3930000000-6800151137f550b0b24fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0029000000-87d6fc7041cc0a8ae488Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-4189000000-1718640f639f14c8ffbcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fu-9270000000-c5c258e619a7caf0d202Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fb9-0049000000-d4507ba5008088f43bb2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1096000000-f48fc1c59c03b2f4eeedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-1390000000-583fd193eccec822fff6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0019000000-282ccc4ee74de31656ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fu-4049000000-f096fd02d1574a188595Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06dl-5390000000-4b659d3b0f488353d51dSpectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (5) Absorption is rapid and complete after oral or intramuscular administration.
Mechanism of ToxicityErgoline alkaloids tend to act as a group, producing complex and variable effects of partial agonism or antagonism at adrenergic, dopaminergic, and serotonergic receptors. Variables relating to these effects are influenced by the agent, dosage, species, tissue, physiological, and endocrinological state, and experimental conditions. In particular, ergoline alkaloids have been shown to have the significant affinity towards the 5-HT1 and 5-HT2 serotonin receptors, D1 and D2 dopamine receptors, and alpha-adrenergic receptors. This can result in a number of different effects, including vasoconstriction, convulsions, and hallucinations. Ergometrine is also known to have a non-receptor specific oxytocic activity. (2, 3, 4)
MetabolismHepatic. Route of Elimination: Thought to be eliminated by non-renal mechanisms (i.e. hepatic metabolism, excretion in feces) Half Life: t1/2 α=10 minutes; t1/2 β=2 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesErgoline alkaloids occur in various species of vines of the Convolvulaceae (morning glory) family and in some species of lower fungi. Ergometrine can also be synthesized from (+)-lysergic acid and L-(+)-2-aminopropanol. It has medical use in obstetrics to facilitate delivery of the placenta and to prevent bleeding after childbirth by causing smooth muscle tissue in the blood vessel walls to narrow, thereby reducing blood flow. For this is usually combined with oxytocin (Syntocinon) as syntometrine. (6, 9)
Minimum Risk LevelNot Available
Health EffectsIngestion of ergoline alkaloids is known to cause the disease ergotism. Ergotism occurs in two forms, gangrenous and convulsive, likely depending on the different kinds and amounts of ergoline alkaloids present. (1)
SymptomsConvulsive ergotism can cause painful seizures and spasms, diarrhea, paresthesias, itching, headaches, nausea and vomiting. Usually the gastrointestinal effects precede the central nervous system effects. As well as seizures there can be hallucinations and mental effects including mania or psychosis. Gangrenous ergotism causes dry gangrene as a result of vasoconstriction induced in the more poorly vascularized distal structures, such as the fingers and toes. Symptoms include desquamation, weak periphery pulse, loss of peripheral sensation, edema and ultimately the death and loss of affected tissues. (7)
TreatmentTreatment for ergotism consists of vasodilators, anticoagulants and low molecular weight dextrans. If necessary, a sympathetic nerve blockade may be carried out, such as brachial plexus blockade. Temporary sedation (e.g. haloperidol) will be necessary in hallucination and diazepam is used for convulsions. There is no specific antidote. (8)
Concentrations
Not Available
DrugBank IDDB01253
HMDB IDHMDB0015383
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00001722
BiGG IDNot Available
BioCyc IDCPD-14457
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkErgometrine
Chemspider ID391970
ChEBI ID4822
PubChem Compound ID443884
Kegg Compound IDC07543
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15038775
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16147681
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18326144
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=2195299
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24173606
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24365208
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=25036782
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=25252517
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=25347567
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=6457611
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=7190615
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=887503