80038-06-8

Basic information

• Product Name: Vinpocetine
• Synonyms: (+)-Apovincaminic acid ethyl ester; (+)-cis-Apovincaminic acid ethyl ester; 3-alpha,16-alpha-Apovincaminic acid ethyl ester; AY 27,255; Apovincaminate d'ethyle; Apovincaminate d'ethyle [French]; Apovincaminic acid ethyl ester; BRN 0900803; Cavinton; Ethyl (+)-apovincaminate; Ethyl (+)-cis-apovincaminate; Ethyl apovincamin-22-oate; RGH 4405; RGH-4405; TCV-3B; UNII-543512OBTC; Vinpocetinum; Vinpocetinum [INN-Latin]; cis-Apovincaminic acid ethyl ester; Eburnamenine-14-carboxylic acid, ethyl ester, (3-alpha,16-alpha)-; Eburnamenine-14-carboxylic acid, ethyl ester, (3alpha,16alpha)-; ethyl eburnamenine-14-carboxylate; ethyl (3alpha,16alpha)-eburnamenine-14-carboxylate; (3alpha,16alpha)-14-(ethoxycarbonyl)eburnamenin-4-ium
• CAS NO: 80038-06-8
• Molecular Formula: C22H26N2O2
• Molecular Weight: 350.45404
• EINECS: 256-028-0
• Mol File: 80038-06-8.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 419.5°C at 760 mmHg
• Flash Point: 207.506°C
• Appearance: /
• Vapor Pressure: 0mmHg at 25°C
• CAS DataBase Reference: Vinpocetine(CAS DataBase Reference)
• NIST Chemistry Reference: Vinpocetine(80038-06-8)
• EPA Substance Registry System: Vinpocetine(80038-06-8)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: R22:
• Safety Statements: S36:
• Hazardous Substances Data: 80038-06-8(Hazardous Substances Data)

Usage

General Description

Vinpocetine is a synthetic chemical derived from the periwinkle plant, commonly used as a dietary supplement for its potential cognitive and memory-enhancing effects. It works by increasing blood flow to the brain and acting as a neuroprotective agent, which may help improve cognitive function, attention, and memory. Vinpocetine is also believed to have anti-inflammatory and antioxidant properties, making it a popular ingredient in nootropic and brain health supplements. However, its safety and efficacy as a cognitive enhancer are still under debate, and long-term use may have potential side effects and interactions with certain medications. Therefore, it is important to use vinpocetine under the guidance of a healthcare professional.

InChI:InChI=1/C22H26N2O2/c1-3-22-11-7-12-23-13-10-16-15-8-5-6-9-17(15)24(19(16)20(22)23)18(14-22)21(25)26-4-2/h5-6,8-9,14,20H,3-4,7,10-13H2,1-2H3/p+1/t20-,22+/m1/s1

Upstream product

• 141-52-6 sodium ethanolate 
• 1617-90-9 vincamin 
• 74904-40-8 (10R,11R,11aS,11bR)-11a-Ethyl-11-hydroxy-2,3,4,5,10,11,11a,11b-octahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester 
• 105221-74-7 ethyl (1S,12bR)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-1-(2'-hydroxyimino)propionate 
• 23944-43-6 (1S,trans)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-propanoic acid methyl ester 
• 85647-42-3 3-((1S,12bR)-1-Ethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-1-yl)-2-[(E)-hydroxyimino]-propionic acid methyl ester 
• 56942-60-0 eburnamenine-14-carboxylic acid methyl ester 
• 86708-31-8 3-((1R,12bR)-1-Ethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-1-yl)-2-[(E)-hydroxyimino]-propionic acid methyl ester 
• 74345-59-8 methyl (1R,12bR)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-propionate 
• 38990-18-0 apovincamine 
• 101978-25-0 ethyl (1R,12bS)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-1-(2'-hydroxyimino)propionate 
• 85717-28-8 methyl (1R,12bS)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-propionate 
• 85647-35-4 methyl (1R,12bS)-1-ethyl-1,2,3,4,6,7,12,12b-octahydro-α-(hydroxyimino)indolo<2,3-a>quinolizine-1-propionate 
• 89825-94-5 14,15-dehydro-16-epivincamine 

Relevant articles and documents

Preparation method of vinpocetine

The invention provides a preparation method of vinpocetine, which relates to the technical field of synthesis of medical intermediates, and comprises the following steps: (1) respectively feeding an ethanol solution of vincamine and an ethanol solution of sodium ethoxide into a premixer for premixing to form a mixed solution 1; (2) sending the mixed solution 1 obtained in the step (1) to a micro-channel module for complete reaction, and outputting the generated reaction solution to a transfer storage tank; (3) respectively feeding the solution and the mixed acid in the transfer storage tank obtained in the step (2) into a premixer for premixing to form a mixed solution 2; (4) sending the mixed solution 2 obtained in the step (3) to a micro-channel module for complete reaction, and outputting the generated reaction solution to a neutralization kettle; and (5) after the reaction is finished, carrying out post-treatment on the material in the neutralization kettle obtained in the step (4) to obtain the target product vinpocetine. The method has the advantages of high atom utilization rate, high selectivity, high yield and less solid waste, is beneficial to environmental protection, and is convenient for industrial production and utilization.

A semi-synthetic synthesis process of vinpocetine

The invention provides a vinpocetine semisynthesis process. The vinpocetine is obtained through hydrolysis, dehydration and esterification reactions by a one-pot method, and after the reactions are finished, extraction separation, purification and crystallization are performed, and finally, the high-content and high-purity product can be obtained. The method is few in reaction steps, simple in process flow, high in vinpocetine yield, simple in equipment, and green and environment-friendly in production procedure, and has tremendous economic and social benefits.

Synthesis and evaluation of 2′-hydroxyethyl trans-apovincaminate derivatives as antioxidant and cognitive enhancer agents

A series of trans-2′-hydroxyethyl and 2′-acyloxyethyl apovincaminates 4b-f and 7b-f has been synthesized and evaluated for their antioxidant and antiamnesic effects. The new esters were prepared from 4a and 7a ethyl esters or from the corresponding carbox