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T3D3685 - Ergometrine

Record Information
Version 1.0
Creation Date 2010-04-21 17:59:34 UTC
Update Date 2013-04-25 08:48:34 UTC
Accession Number T3D3685
Identification
Common Name Ergometrine
Description Ergometrine is an alkaloid of the ergoline family. Like other ergoline alkaloids, it occurs 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. Long term exposure to some ergoline alkaloids can cause ergotism, a disease causing convulsive and gangrenous symptoms. (W721, W727, W730)
Compound Type
  • Organic Compound
  • Mycotoxin
Chemical Structure
Thumb
MOL SDF SMILES InChI
Synonyms
  1. (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)-amide
  2. 7-Methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid (2-hydroxy-1-methyl-ethyl)-amide, maleate
  3. 9,10-Didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergoline-8beta(S)-carboxamide
  4. 9,10-Didehydro-N-(alpha-(hydroxymethyl)ethyl)-6-methylergoline-8-beta-carboxamide
  5. Basergin
  6. D-Lysergic acid 1-hydroxymethylethylamide
  7. D-Lysergic acid-L-propanolamide
  8. Ergobasin
  9. Ergobasine
  10. Ergoklinine
  11. Ergoline-8-beta-carboxamide, 9,10-didehydro-N-((S)-2-hydroxy-1-methylethyl)-6-methyl-
  12. Ergoline-8-carboxamide, 9,10-didehydro-N-(2-hydroxy-1-methylethyl)-6-methyl-, (8beta(S))-
  13. Ergometrin
  14. Ergometrina
  15. Ergometrina [spanish]
  16. Ergometrine
  17. ergometrine maleate
  18. Ergometrinine
  19. Ergometrinum
  20. Ergometrinum [latin]
  21. Ergostetrine
  22. Ergotocine
  23. Ergotrate
  24. Ergotrate Maleate
  25. Ergovine
  26. L-Lysergic-L(beta-hydroxyisopropylamide)
  27. Lysergamide, N-((S)-2-hydroxy-1-methylethyl)-
  28. Lysergic acid propanolamide
  29. Margonovine
  30. N-(1-(Hydroxymethyl)ethyl)-D-lysergamide
  31. N-(2-Hydroxy-1-methylethyl)-D(+)-lysergamide
  32. N-(alpha-(Hydroxymethyl)ethyl)-D-lysergamide
  33. Neofemergen
  34. Secacornin
  35. Secometrin
Chemical Formula C19H23N3O2
Average Molecular Weight 325.4048
Monoisotopic Molecular Weight 325.179026995
Chemical IUPAC Name
ergonovine
CAS Registry Number 60-79-7
SMILES
CC(CO)NC(=O)C1CN(C)C2CC3=CNC4=CC=CC(=C34)C2=C1
InChI Identifier
InChI=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)
InChI Key InChIKey=WVVSZNPYNCNODU-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Heterocyclic Compounds
Class Quinolines and Derivatives
Sub Class Indoloquinolines
Direct Parent Ergolines
Alternative Parents
  • Benzoquinolines
  • Pyrroloquinolines
  • Quinoline Carboxamides
  • N-substituted Nicotinamides
  • Isoindoles and Derivatives
  • Indoles
  • Tetrahydropyridines
  • Benzene and Substituted Derivatives
  • Pyrroles
  • Trialkylamines
  • Secondary Carboxylic Acid Amides
  • Primary Alcohols
  • Cycloalkenes
  • Enolates
  • Alkanolamines
Molecular Framework Aromatic Heteropolycyclic Compounds
Substituents
  • benzene
  • cycloalkene
  • organonitrogen compound
  • enolate
  • secondary carboxylic acid amide
  • carboxamide group
  • alkanolamine
  • alcohol
  • tertiary aliphatic amine (trialkylamine)
  • tertiary amine
  • primary alcohol
  • pyrrole
  • indole
  • isoindole or derivative
  • indole or derivative
  • benzoquinoline
  • quinoline-3-carboxamide
  • pyrroloquinoline
  • n-substituted nicotinamide
  • tetrahydropyridine
External Descriptors Not Available
DrugBank ID Not Available
PubChem Compound ID 443884 Link_out
KEGG ID Not Available
UniProt ID Not Available
OMIM ID Not Available
ChEBI ID Not Available
BioCyc ID Not Available
CTD ID Not Available
Stitch ID Not Available
PDB ID Not Available
ACToR ID Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Ergometrine Link_out
Physical Properties
Appearance Not Available
Melting Point Not Available
Solubility Not Available
Predicted LogP 1.0706959856666662
Toxicity Profile
Route of Exposure Oral, dermal, inhalation, and parenteral (contaminated drugs). (W967)
Mechanism of Action Ergoline 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. (W726, W727, W728)
Metabolism Not Available
Toxicity Values Not Available
Lethal Dose Not Available
Carcinogenicity (IARC Classification) Not Available
Uses/Sources Ergoline 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. (W721, W730)
Minimum Risk Level Not Available
Health Effects Ingestion 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. (W723)
Symptoms Convulsive 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. (W724)
Treatment Treatment 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. (W725)
References
General References
  • W727 — Schiff PL. Ergot and its alkaloids. Am J Pharm Educ. 2006 Oct 15;70(5):98. [17149427 Link_out]
  • W724 — Wikipedia. Ergotism. Last Updated 6 April 2010. [Link]
  • W730 — Wikipedia. Ergometrine. Last Updated 24 February 2010. [Link]
  • W721 — Wikipedia. Ergoline. Last Updated 2 April 2010. [Link]
  • W726 — Mantegani S, Brambilla E, Varasi M. Ergoline derivatives: receptor affinity and selectivity. Farmaco. 1999 May 30;54(5):288-96. [10418123 Link_out]
  • W728 — Kvernmo T, Härtter S, Burger E. A review of the receptor-binding and pharmacokinetic properties of dopamine agonists. Clin Ther. 2006 Aug;28(8):1065-78. [16982285 Link_out]
  • W725 — Van den Enden, E. (2004). Illustrated Lecture Notes on Tropical Medicine. [Link]
  • W723 — Toxicology of mycotoxins. Some major mycotoxins and their mycotoxicoses--an overview. Int J Food Microbiol. 2007 Oct 20;119(1-2):3-10. Epub 2007 Jul 31. [17719115 Link_out]
  • W967 — Peraica M, Domijan AM. Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 Link_out]

Targets

1. 5-hydroxytryptamine receptor 2A

This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production.

Ergometrine acts as an agonist at 5-HT2 receptors, causing direct stimulation of the uterine smooth musculature, resulting in increased muscular tone and an enhancement of the rate and force of rhythmical contractions. (W727)
UniProt ID: P28223 Link_out
Gene: HTR2A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W727 — Schiff PL. Ergot and its alkaloids. Am J Pharm Educ. 2006 Oct 15;70(5):98. [17149427 Link_out]

2. 5-hydroxytryptamine receptor 2B

This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Plays a role in the regulation of impulsive behavior.

Ergometrine acts as an agonist at 5-HT2 receptors, causing direct stimulation of the uterine smooth musculature, resulting in increased muscular tone and an enhancement of the rate and force of rhythmical contractions. (W727)
UniProt ID: P41595 Link_out
Gene: HTR2B Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W727 — Schiff PL. Ergot and its alkaloids. Am J Pharm Educ. 2006 Oct 15;70(5):98. [17149427 Link_out]

3. 5-hydroxytryptamine receptor 2C

This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system.

Ergometrine acts as an agonist at 5-HT2 receptors, causing direct stimulation of the uterine smooth musculature, resulting in increased muscular tone and an enhancement of the rate and force of rhythmical contractions. (W727)
UniProt ID: P28335 Link_out
Gene: HTR2C Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W727 — Schiff PL. Ergot and its alkaloids. Am J Pharm Educ. 2006 Oct 15;70(5):98. [17149427 Link_out]

4. D(2) dopamine receptor

Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase (By similarity).

Ergometrine acts as an agonist at the D2 dopamine receptor, inhibiting cyclic AMP production. (W729)
UniProt ID: P14416 Link_out
Gene: DRD2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W729 — Larson BT, Harmon DL, Piper EL, Griffis LM, Bush LP. Alkaloid binding and activation of D2 dopamine receptors in cell culture. J Anim Sci. 1999 Apr;77(4):942-7. [10328360 Link_out]

5. Alpha-1A adrenergic receptor

This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes.

Ergometrine is partitally agonistic of alpha-adrenergic receptors. (W727)
UniProt ID: P35348 Link_out
Gene: ADRA1A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W727 — Schiff PL. Ergot and its alkaloids. Am J Pharm Educ. 2006 Oct 15;70(5):98. [17149427 Link_out]

6. Alpha-1B adrenergic receptor

This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine (PE)-stimulated ERK signaling in cardiac myocytes.

Ergometrine is partitally agonistic of alpha-adrenergic receptors. (W727)
UniProt ID: P35368 Link_out
Gene: ADRA1B Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W727 — Schiff PL. Ergot and its alkaloids. Am J Pharm Educ. 2006 Oct 15;70(5):98. [17149427 Link_out]

7. Alpha-1D adrenergic receptor

This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium.

Ergometrine is partitally agonistic of alpha-adrenergic receptors. (W727)
UniProt ID: P25100 Link_out
Gene: ADRA1D Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W727 — Schiff PL. Ergot and its alkaloids. Am J Pharm Educ. 2006 Oct 15;70(5):98. [17149427 Link_out]

8. Alpha-2A adrenergic receptor

Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol.

Ergometrine is partitally agonistic of alpha-adrenergic receptors. (W727)
UniProt ID: P08913 Link_out
Gene: ADRA2A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W727 — Schiff PL. Ergot and its alkaloids. Am J Pharm Educ. 2006 Oct 15;70(5):98. [17149427 Link_out]

9. Alpha-2B adrenergic receptor

Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol.

Ergometrine is partitally agonistic of alpha-adrenergic receptors. (W727)
UniProt ID: P18089 Link_out
Gene: ADRA2B Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W727 — Schiff PL. Ergot and its alkaloids. Am J Pharm Educ. 2006 Oct 15;70(5):98. [17149427 Link_out]

10. Alpha-2C adrenergic receptor

Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins.

Ergometrine is partitally agonistic of alpha-adrenergic receptors. (W727)
UniProt ID: P18825 Link_out
Gene: ADRA2C Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
References:
  • W727 — Schiff PL. Ergot and its alkaloids. Am J Pharm Educ. 2006 Oct 15;70(5):98. [17149427 Link_out]