CHEBI:4822 - ergometrine

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ChEBI Name ergometrine
ChEBI ID CHEBI:4822
Definition A monocarboxylic acid amide that is lysergamide in which one of the hydrogens attached to the amide nitrogen is substituted by a 1-hydroxypropan-2-yl group (S-configuration). An ergot alkaloid that has a particularly powerful action on the uterus, its maleate (and formerly tartrate) salt is used in the active management of the third stage of labour, and to prevent or treat postpartum of postabortal haemorrhage caused by uterine atony: by maintaining uterine contraction and tone, blood vessels in the uterine wall are compressed and blood flow reduced.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:296351
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Formula C19H23N3O2
Net Charge 0
Average Mass 325.40480
Monoisotopic Mass 325.179
InChI 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)/t11-,13+,17+/m0/s1
InChIKey WVVSZNPYNCNODU-XTQGRXLLSA-N
SMILES C[C@@H](CO)NC(=O)[C@H]1CN(C)[C@@H]2Cc3c[nH]c4cccc(C2=C1)c34
Metabolite of Species Details
Claviceps purpurea (NCBI:5111) See: PubMed
Claviceps purpurea (NCBI:5111) See: PubMed
Roles Classification
Biological Role(s): toxin
Poisonous substance produced by a biological organism such as a microbe, animal or plant.
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
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): oxytocic
A drug that stimulates contraction of the myometrium. Oxytocics are used to induce labour, obstetric at term, to prevent or control postpartum or postabortion haemorrhage, and to assess foetal status in high risk pregnancies. They may also be used alone or with other drugs to induce abortions (abortifacients).
diagnostic agent
A substance administered to aid diagnosis of a disease.
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ChEBI Ontology
Outgoing ergometrine (CHEBI:4822) has parent hydride ergoline (CHEBI:38484)
ergometrine (CHEBI:4822) has role diagnostic agent (CHEBI:33295)
ergometrine (CHEBI:4822) has role fungal metabolite (CHEBI:76946)
ergometrine (CHEBI:4822) has role oxytocic (CHEBI:36063)
ergometrine (CHEBI:4822) has role toxin (CHEBI:27026)
ergometrine (CHEBI:4822) is a ergot alkaloid (CHEBI:23943)
ergometrine (CHEBI:4822) is a monocarboxylic acid amide (CHEBI:29347)
ergometrine (CHEBI:4822) is a organic heterotetracyclic compound (CHEBI:38163)
ergometrine (CHEBI:4822) is a primary alcohol (CHEBI:15734)
ergometrine (CHEBI:4822) is a secondary amino compound (CHEBI:50995)
ergometrine (CHEBI:4822) is a tertiary amino compound (CHEBI:50996)
Incoming ergometrine maleate (CHEBI:31554) has part ergometrine (CHEBI:4822)
IUPAC Name
N-[(2S)-1-hydroxypropan-2-yl]-6-methyl-9,10-didehydroergoline-8β-carboxamide
INNs Sources
ergometrina ChemIDplus
ergométrine WHO MedNet
ergometrine ChemIDplus
ergometrinum ChemIDplus
Synonyms Sources
(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 ChEMBL
9,10-didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergoline-8β(S)-carboxamide ChemIDplus
9,10-didehydro-N-(α-(hydroxymethyl)ethyl)-6-methylergoline-8-β-carboxamide ChemIDplus
[8β(S)]-9,10-didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergoline-8-carboxamide ChEBI
D-lysergic acid 1-hydroxymethylethylamide ChemIDplus
D-lysergic acid-L-propanolamide ChemIDplus
ergobasine ChemIDplus
Ergometrine KEGG COMPOUND
Ergonovine KEGG COMPOUND
ergotocine ChemIDplus
margonovine ChemIDplus
N-(2-Hydroxy-1-methylethyl)-D-(+)-lysergamide ChemIDplus
N-(α-(hydroxymethyl)ethyl)-D-lysergamide ChemIDplus
Database Links Databases
1042 DrugCentral
C00001722 KNApSAcK
C07543 KEGG COMPOUND
CPD-14457 MetaCyc
D07905 KEGG DRUG
DB01253 DrugBank
Ergometrine Wikipedia
US2736728 Patent
US2809920 Patent
US3141887 Patent
View more database links
Registry Numbers Types Sources
60-79-7 CAS Registry Number ChemIDplus
94902 Beilstein Registry Number Beilstein
94902 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15038775 PubMed citation Europe PMC
16147681 PubMed citation Europe PMC
18326144 PubMed citation Europe PMC
2195299 PubMed citation Europe PMC
24173606 PubMed citation Europe PMC
24365208 PubMed citation Europe PMC
25036782 PubMed citation Europe PMC
25252517 PubMed citation Europe PMC
25347567 PubMed citation Europe PMC
6457611 PubMed citation Europe PMC
7190615 PubMed citation ChEMBL
887503 PubMed citation Europe PMC
Last Modified
22 February 2017