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

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

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

• 64-17-5 ethanol 
• 4880-92-6 apovincamine 
• 141-52-6 sodium ethanolate 
• 105-39-5 chloroacetic acid ethyl ester 
• 51152-47-7 (1R*,5S*,12bS*)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-carbaldehyde 
• 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 
• 56942-60-0 eburnamenine-14-carboxylic acid methyl ester 
• 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 
• 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 
• 74904-40-8 (10R,11R,11aS,11bS)-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 
• 74904-40-8 (10S,11S,11aS,11bS)-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 
• 74904-40-8 (10S,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 
• 74904-40-8 (10S,11S,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 
• 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 

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.

Method for preparing vinpocetine

The invention relates to a method for preparing a compound, specifically to a method for preparing vinpocetine. The method comprises the following steps: 1) preparation of a vinpocetine crude product, including, mixing an apovincamine ethanol solution and a sodium ethoxide ethanol solution for a reflux reaction, removing the solvent, adding ethanol, carrying out a reflux reaction of the sodium ethoxide ethanol solution, when the residual content of apovincamine is less than 0.3% of the added apovincamine raw material, performing hot filtration, removing a part of solvent of the filtered liquid, and performing cooling crystallization, solid-liquid separation, washing and drying to obtain the vinpocetine crude product; and 2) refining of vinpocetine, including adding active carbon, performing hot filtration, and performing recrystallization with ethanol for refining to obtain vinpocetine. The method is short and simple in process. The prepared vinpocetine is high in yield and purity, meets the standard of the European Pharmacopoeia (EP) 6.0, and is easy for industrial production.

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.

Process for the preparation of vinpocetine and apovincamine

A process for the preparation of vinpocetine and apovincamine, wherein said process comprises the steps of: (1) preparing a solution of the compound of formula (II) below and an organic or inorganic base in a polar aprotic solvent, and (2) adding an alkyl haloacetate to the solution of step (1) under controlled temperature conditions.

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

Compositions of a cyclooxygenase-2 selective inhibitor and a sodium ion channel blocker for the treatment of pain, inflammation or inflammation mediated disorders

The present invention provides compositions and methods for the treatment of pain, inflammation or inflammation-mediated disorders in a subject. More particularly, the invention provides a combination therapy for the treatment of pain, inflammation or inflammation mediated disorders comprising the administration to a subject of a sodium ion channel blocker in combination with a cyclooxygenase-2 selective inhibitor.

Synthesis of pentacyclic ring systems, indolo[2,3-a][1,2]-oxazino[5,6-i]quinolizine and indolo[2,3-a]pyrano[3,2-i]-quinolizine, and their application for the synthesis of eburnamine-vincamine alkaloids

15a-Ethyl-14-carboxylic esters of the title pentacycles (6) and (8) were prepared via Wenkert's enamine (4). Both compounds can be readily transformed into indoloquinolizinylpyruvate oxime esters (5), key intermediates for the synthesis of vincamine alkal

APOVINCAMINIC ACID DERIVATIVE AND MEDICINE CONTAINING THE SAME

This invention relates to an apovincaminic acid derivative represented by the following formula (1): wherein R1represents a lower alkyl group, and R2represents an aryl group, which may be substituted by 1 to 5 substituents selected from halogen atoms and lower alkyl, lower alkoxy, lower alkoxycarbonyl, acylamino and nitro groups, a benzyl group, a quinolyl group or a thienyl group, or an acid addition salt thereof; and also to a drug containing the same. This compound has excellent vasodilating activity and platelet aggregation inhibiting activity, and can be used for the treatment of cerebrovascular disorder, thromboembolism and chronic arterial occlusive diseases and also for the improvement of blood flow disturbances.

A facile one-pot synthesis of vinpocetine

A one-pot synthesis of vinpocetine from vincamine was established. Lewis acids caused transesterification and/or dehydration of vincamine in EtOH. FeCl3 catalyzed both transesterification and dehydration while Ti(OEt)4 selectively catalyzed transesterification.

Syntheses and Cardiovascular Activity of Stereoisomers and Derivatives of Eburnane Alkaloids

The synthesis of all the possible isomers of the eburnamenine-vincamine type alkaloids 1b, 2a*, 3a and derivatives 4, 8, 9, 10 is described.Structures were determined by 1H- and 13C-NMR spectroscopy including special techniques such as DR, DEPT, DNOE, and 2D-HSC.In contrast to the known cerebrovascular effects of cis-(3S,16S) compounds, trans-(3S,16R) derivatives show a significant peripheral vasodilator effect. Key Word: Eburnanes / Alkaloids / Cardiovascular effects / Indoloquinolizines