Levosulpiride

Base Information

• Chemical Name: Levosulpiride
• CAS No.: 23672-07-3
• Molecular Formula: C₁₅H₂₃N₃O₄S
• Molecular Weight: 341.431
• Hs Code.: 29350090
• European Community (EC) Number: 682-417-3
• UNII: JTG7R315LK
• DSSTox Substance ID: DTXSID0042583
• Nikkaji Number: J60.441K
• Wikipedia: Levosulpiride
• Wikidata: Q1452256
• NCI Thesaurus Code: C90840
• Pharos Ligand ID: LALNKV1WXMP1
• Metabolomics Workbench ID: 63163
• ChEMBL ID: CHEMBL267044
• Mol file: 23672-07-3.mol

Synonyms:levopraid;levosulpiride;N-(((S)-1-ethyl-2-pyrrolidinyl)methyl)-5-sulfamoyl-o-anisamide;RV-12309

Chemical Property of Levosulpiride

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 183-186 °C(lit.)
• Refractive Index: 1.551
• PKA: 9.98±0.60(Predicted)
• PSA: 110.11000
• Density: 1.236 g/cm³
• LogP: 2.66660
• Storage Temp.: 2-8°C
• Solubility.: DMF (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 341.14092740
• Heavy Atom Count: 23
• Complexity: 505

Purity/Quality:

99.9% ^*data from raw suppliers

Levopride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCN1CCCC1CNC(=O)C2=C(C=CC(=C2)S(=O)(=O)N)OC
• Isomeric SMILES: CCN1CCC[C@H]1CNC(=O)C2=C(C=CC(=C2)S(=O)(=O)N)OC
• Recent ClinicalTrials: Helicobacter Pylori Eradication in Functional Dyspepsia
• Uses: dopamine receptor antagonists Dopamine D2 and D3-receptor antagonist. Antipsychotic; antidepressant; antiemetic. (S)-(?)-Sulpiride was used to study the effect of dopamine D2 receptor function on activation of KCNQ potassium channels10 and on depression-like behavior in ovariectomized female rats.11

Technology Process of Levosulpiride

There total 2 articles about Levosulpiride 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: 93.8%

methyl 2-methoxy-5-sulfamoyl-benzoate (33045-52-2) + (S)-2-(Aminomethyl)-1-ethylpyrrolidine (22795-99-9) → (S)-(-)-sulpiride (15676-16-1,23672-06-2,23672-07-3,23756-79-8)

Guidance literature:

at 90 - 100 ℃; for 5h; Inert atmosphere;

Reference yield: 90.3%

2-methoxy-5-sulfamoylbenzoic acid ethyl ester (33045-53-3) + (S)-2-(Aminomethyl)-1-ethylpyrrolidine (22795-99-9) → (S)-(-)-sulpiride (15676-16-1,23672-06-2,23672-07-3,23756-79-8)

Guidance literature:

In isopropyl alcohol; at 80 ℃; for 36h; Solvent; Temperature;

Reference yield: 20.0%

(S)-(-)-sulpiride (15676-16-1,23672-06-2,23672-07-3,23756-79-8) → (S)-3-(((1-ethylpyrrolidin-2-yl)methyl)carbamoyl)-4-methoxybenzenesulfonyl azide (1609375-68-9)

Guidance literature:

With 3-azidosulfonyl-3H-imidazole-1-ium hydrogen sulfate; potassium carbonate; In water; isopropyl alcohol; at 20 ℃; for 48h;

DOI:10.1021/jo500553q

upstream raw materials:

2-methoxy-5-sulfamoylbenzoic acid ethyl ester

(S)-2-(Aminomethyl)-1-ethylpyrrolidine

methyl 2-methoxy-5-sulfamoyl-benzoate

Downstream raw materials:

(S)-3-(((1-ethylpyrrolidin-2-yl)methyl)carbamoyl)-4-methoxybenzenesulfonyl azide

Refernces

• 1、 -. "Process for the enantiomeric resolution of 1-substituted 2-(aminomethyl)-pyrrolidines by amidation in the presence of lipases". . . Retrieved 2008/06/13.