66644-81-3

Basic information

• Product Name: N-(1-Allyl-2-pyrrolidinyl)methyl-2,3-dimethoxy-5-sulfamoylbenzamide
• Synonyms: VERALIPRIDE;N-(1-Allyl-2-pyrrolidinyl)methyl-2,3-dimethoxy-5-sulfamoylbenzamide;N-[(1-Allyl-2-pyrrolidinyl)methyl]-5-sulphamoyl-2-veratramide;Velaripride;2,3-diMethoxy-N-{[1-(prop-2-en-1-yl)pyrrolidin-2-yl]Methyl}-5-sulfaMoylbenzaMide
• CAS NO: 66644-81-3
• Molecular Formula: C₁₇H₂₅N₃O₅S
• Molecular Weight: 383.46
• EINECS: 266-435-5
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Isotope Labelled Compounds;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 66644-81-3.mol
• Article Data: 1

Chemical Properties

• Melting Point: 128 °C
• Appearance: /
• Density: 1.23 g/cm³
• Refractive Index: 1.547
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• PKA: 10.02±0.60(Predicted)
• CAS DataBase Reference: N-(1-Allyl-2-pyrrolidinyl)methyl-2,3-dimethoxy-5-sulfamoylbenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(1-Allyl-2-pyrrolidinyl)methyl-2,3-dimethoxy-5-sulfamoylbenzamide(66644-81-3)
• EPA Substance Registry System: N-(1-Allyl-2-pyrrolidinyl)methyl-2,3-dimethoxy-5-sulfamoylbenzamide(66644-81-3)

Safety Data

• Hazardous Substances Data: 66644-81-3(Hazardous Substances Data)

Usage

Originator

Agreal,Delagrange,France,1980

Uses

Different sources of media describe the Uses of 66644-81-3 differently. You can refer to the following data:
1. Veralipride, a synthetic benzamide derivative with antidopaminergic action, is effective in reducing the frequency and severity of hot flashes associated with menopausal hypoestrogenism, gaining interest as a non-hormonal treatment for climacteric flushing.
2. Labelled Veralipride, a synthetic benzamide derivative with antidopaminergic action, is effective in reducing the frequency and severity of hot flashes associated with menopausal hypoestrogenism, gain ing interest as a non-hormonal treatment for climacteric flushing.

Manufacturing Process

7.8 g (0.03 mol) of 2,3-dimethoxy-5-sulfamoylbenzoic acid, 200 ml of tetrahydrofuran and 7.3 g (0.045 mol) of carbonyldimidazole are placed in a 500 ml flask fitted with an agitator, a thermometer and a condenser.The mixture is agitated for 30 minutes at normal temperature, then 6.7 g (0.948 mol) of 1-allyl-2-aminomethylpyrrolidine is added. The mixture is left under agitation for 5 hours at 20°C, then the solvent is evaporated under vacuum and the residue treated with 150 ml of water. The crystals are washed and dried. 6.9 g of N-(1'-allyl-2'-pyrrolidyl-methyl)-2,3-dimethoxy-5-sulfamoyl- benzamide is obtained. Yield is 60%; melting point 113°C to 114°C.

Therapeutic Function

Menopause treatment

InChI:InChI=1/C17H25N3O5S/c1-4-7-20-8-5-6-12(20)11-19-17(21)14-9-13(26(18,22)23)10-15(24-2)16(14)25-3/h4,9-10,12H,1,5-8,11H2,2-3H3,(H,19,21)(H2,18,22,23)

Upstream product

• 66644-82-4 2,3-dimethoxy-5-sulfonamidobenzoic acid methyl ester 
• 26116-13-2 1-allyl-2-aminomethyl-pyrrolidine 
• 66644-80-2 2,3-dimethoxy-5-sulphamoyl benzoic acid 
• 64269-79-0 Carbonyldiimidazole 

Downstream Products

• 1370524-59-6 [Cu(N-((1-allyl-2-pyrrolidinyl)methyl)-5-sulfamoyl-2-veretramide)2Cl₂(H₂O)2] 
• 1370524-61-0 [Zn(N-((1-allyl-2-pyrrolidinyl)methyl)-5-sulfamoyl-2-veretramide)2Cl₂(H₂O)2] 

Relevant articles and documents

N-(1-allyl-2-pyrrolidylmethyl)-2,3-dimethoxy-5-sulfamoylbenzamide and derivatives thereof and method for treating hot flushes associated with natural or surgical menopause

N-(1'-allyl-2'-pyrrolidylmethyl)-2,3-dimethoxy-5-sulfamoylbenzamide and dvatives thereof and method for treating the psycho neuro-vegetative syndrome of the natural or surgical menopause by administering an effective amount of said compound to a patient.