Ergometrine

Base Information

• Chemical Name: Ergometrine
• CAS No.: 60-79-7
• Deprecated CAS: 11002-48-5,78207-83-7
• Molecular Formula: C19H23N3O2
• Molecular Weight: 325.411
• European Community (EC) Number: 200-485-0
• UNII: WH41D8433D
• DSSTox Substance ID: DTXSID8046323
• Nikkaji Number: J4.806B
• Wikipedia: Ergometrine
• Wikidata: Q424508
• NCI Thesaurus Code: C75040
• Pharos Ligand ID: 6ASQ5JCCTA55
• Metabolomics Workbench ID: 43460
• ChEMBL ID: CHEMBL119443
• Mol file: 60-79-7.mol

Synonyms:Ergobasin;Ergometrin;Ergometrine;Ergometrine Maleate;Ergonovine;Ergonovine Maleate;Ergotrate

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Chemical Property of Ergometrine

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 5.27E-17mmHg at 25°C
• Melting Point: 162°
• Refractive Index: 1.678
• Boiling Point: 635.2 °C at 760 mmHg
• PKA: 6.8(at 25℃)
• Flash Point: 337.9 °C
• PSA: 68.36000
• Density: 1.3 g/cm³
• LogP: 1.86340
• Water Solubility.: >394g/L(25 oC)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 325.17902698
• Heavy Atom Count: 24
• Complexity: 535

Purity/Quality:

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 23/24/25
• Safety Statements: 36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CO)NC(=O)C1CN(C2CC3=CNC4=CC=CC(=C34)C2=C1)C
• Isomeric SMILES: C[C@@H](CO)NC(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C
• Recent ClinicalTrials: Carbetocin Versus Oxytocin and Ergometrine for the Prevention of Postpartum Hemorrhage
• Recent EU Clinical Trials: Intramuscular oxytocics: A multi-centre randomised comparison study of intramuscular Carbetocin, Syntocinon and Syntometrine for the third stage of labour following vaginal birth
• Uses: Ergonovine is a water-soluble lysergic acidderivative that occurs in ergot. It is used as anoxytocic agent. Its maleate derivative is usedin the treatment of postpartum hemorrhage.

Technology Process of Ergometrine

There total 16 articles about Ergometrine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

ergonovine maleate (129-51-1) → ergometrine (60-79-7)

Guidance literature:

With sodium hydrogencarbonate; In water; ethyl acetate; at 20 ℃; for 0.5h;

DOI:10.3390/molecules25020331

Reference yield: 92.6%

(S)-Alaninol (2749-11-3) + D-lysergic acid (82-58-6) → ergometrine (60-79-7)

Guidance literature:

With dmap; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In tetrahydrofuran; at 20 ℃; for 6h; Reagent/catalyst; Concentration; Solvent; Temperature;

Reference yield:

(S)-Alaninol (2749-11-3) + C16H15ClN2O → ergometrine (60-79-7)

Guidance literature:

With triethylamine; In toluene; at 20 ℃; for 2h; Reagent/catalyst; Solvent; Green chemistry; Industrial scale;

upstream raw materials:

D-lysergic acid

ergonovinine

benzylamine

(S)-Alaninol

Downstream raw materials:

6-methyl-9,10-didehydro-5α-ergoline-8α-carboxylic acid-((R)-β-hydroxy-isopropylamide)

Refernces

• 1、 -. "Preparation method of ergonovine". Paragraph 0054-0062. . Retrieved 2017/08/27.