23672-07-3

Basic information

• Product Name: Levosulpiride
• Synonyms: (s)-(-)-n-((1-ethyl-2-pyrrolidinyl)methyl)-5-sulfamoyl-o-anisamide;(s)-(-)-o-anisamid;5-(aminosulfonyl)-n-((1-ethyl-2-pyrrolidinyl)methyl)-2-methoxy-benzamid(;levopraid;rv-12309;s-(-)-n-(1-ethyl-2-pyrrolidinomethyl)-2-methoxy-5-sulfamoylebenzamide;(-)-5-AMINOSULFONYL-N-[(1-ETHYL-2-PYRROLIDINYL)METHYL]-2-METHOXY-BENZAMIDE;LEVOSULPIRIDE
• CAS NO: 23672-07-3
• Molecular Formula: C₁₅H₂₃N₃O₄S
• Molecular Weight: 341.43
• EINECS: 233-599-4
• Product Categories: API;Dopamine receptor;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;Chiral Reagents;Other APIs
• Mol File: 23672-07-3.mol

Chemical Properties

• Melting Point: 183-186 °C(lit.)
• Appearance: white crystalline powder
• Density: 1.236 g/cm³
• Refractive Index: 1.551
• Storage Temp.: 2-8°C
• Solubility: DMF (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 9.98±0.60(Predicted)
• Merck: 14,8989
• CAS DataBase Reference: Levosulpiride(CAS DataBase Reference)
• NIST Chemistry Reference: Levosulpiride(23672-07-3)
• EPA Substance Registry System: Levosulpiride(23672-07-3)

Safety Data

• RIDADR: 3077
• WGK Germany: 3
• RTECS: BZ3400100
• Hazardous Substances Data: 23672-07-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Levosulpiride is used as a dopamine receptor antagonist for its antipsychotic, antidepressant, and antiemetic properties. It modulates dopamine D2 and D3-receptor function, which aids in the treatment of various psychiatric and mood disorders.
Used in Research Applications:
Levosulpiride is used as a research tool to study the effect of dopamine D2 receptor function on activation of KCNQ potassium channels and on depression-like behavior in animal models, such as ovariectomized female rats. This helps in understanding the underlying mechanisms of dopamine receptor interactions and their role in various physiological and pathological processes.

Biological Activity

Active enantiomer. Selective D 2 -like dopamine antagonist (K i values are ~ 0.015. ~ 0.013, 1, ~ 45 and ~ 77 μ M at D 2 , D 3 , D 4 , D 1 and D 5 receptors respectively).

Biochem/physiol Actions

(S)-(?)-Sulpiride or Levosulpiride blocks the inhibitory enteric D2 receptors (neuronal and muscular). It has prokinetic activity and is effective in the treatment of functional dyspepsia and gastroparesis in insulin-dependent diabetes mellitus patients.7,8 Since dopamine controls human sexual function, (S)-(?)-Sulpiride is reportedly effective in treatment of erectile dysfunctions.9

InChI:InChI=1/C15H23N3O4S/c1-3-18-8-4-5-11(18)10-17-15(19)13-9-12(23(16,20)21)6-7-14(13)22-2/h6-7,9,11H,3-5,8,10H2,1-2H3,(H,17,19)(H2,16,20,21)/t11-/m0/s1

Upstream product

• 33045-52-2 methyl 2-methoxy-5-sulfamoyl-benzoate 
• 22795-99-9 (S)-2-(Aminomethyl)-1-ethylpyrrolidine 
• 33045-53-3 2-methoxy-5-sulfamoylbenzoic acid ethyl ester 

Downstream Products

• 1609375-68-9 (S)-3-(((1-ethylpyrrolidin-2-yl)methyl)carbamoyl)-4-methoxybenzenesulfonyl azide 

Relevant articles and documents

A postoperative or its optical isomers of synthetic and post-processing method

The invention relates to a synthesis and post-processing method of sulpiride or an optical isomer thereof, and the synthesis and post-processing method include the following steps: under inert gas protection, heating 2-methoxy-5-aminosulfonyl methyl benzoate or 2-methoxy-5-aminosulfonyl ethyl benzoate and 1-ethyl-2-aminomethyl pyrrolidine or an optical isomer thereof at 80-120 DEG C for a plurality of hours, and after the reaction is completed, adding ethanol for processing, cooling, filtering, washing and drying.

Process for the enantiomeric resolution of 1-substituted 2-(aminomethyl)-pyrrolidines by amidation in the presence of lipases

A process for the enantiomeric resolution of 1-substituted 2-(aminomethyl)pyrrolidines of formula (I) in which R is C1-C6 alkyl, which process comprises the reaction of the racemic amine with benzyl acetate in acetonitrile in the presence of a lipase selected from Pseudomonas cepacia, Pseudomonas fluorescens or Candida rugosa lipases, to give the corresponding 1-substituted N-(pyrrolidin-2-yl-methyl)-acetamides of formula (II), with R configuration, and the residual amine with S configuration, and, if desired, the subsequent hydrolysis of the amide to obtain the amine with R configuration.

Synthesis and Inhibitory Activity on Carbonic Anhydrase of Some New Sulpiride Analogues Studied by Means of a New Method

The pharmacological activity of several new sulpiride analogues was studied by means of a new approach, based on a potentiometric technique with a pCO2 sensor, capable of detecting carbonic anhydrase inhibition at equilibrium conditions.This procedure gives results stated as percent of inhibition of enzymatic activity (IP, inhibitory power).To prove the reliability of the proposed approach and to study structure-activity relationships, several new molecules were synthesized and tested in comparison with the two sulpiride enantiomers.A possible inhibition mechanism is discussed in terms of experimental evidence obtained from the interactions between the molecular structures of the new synthesized compounds and carbonic anhydrase.