4880-92-6

Basic information

• Product Name: apovincamine
• Synonyms: Methyl (3alpha,16alpha)-eburnamenine-14-carboxylate;Methyl (13aS,13bS)-13a-ethyl-2,3,5,6,13a,13b-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate;methyl (41S,13aS)-13a-ethyl-2,3,41,5,6,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate;apovincamine;(3α,16α)-Eburnamenine-14-carboxylic acid methyl ester;Apo-14,15-dehydrovincamine;Apovincaminic acid methyl;(+)-trans-Cavinton
• CAS NO: 4880-92-6
• Molecular Formula: C₂₁H₂₄N₂O₂
• Molecular Weight: 336.433
• EINECS: 225-491-0
• Mol File: 4880-92-6.mol
• Article Data: 24

Chemical Properties

• Melting Point: 160-162℃
• Boiling Point: 405.7°Cat760mmHg
• Flash Point: 199.1°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 8.61E-07mmHg at 25°C
• Refractive Index: 1.678
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: apovincamine(CAS DataBase Reference)
• NIST Chemistry Reference: apovincamine(4880-92-6)
• EPA Substance Registry System: apovincamine(4880-92-6)

Safety Data

• Hazardous Substances Data: 4880-92-6(Hazardous Substances Data)

Usage

Originator

Apovincamine,GC Promochem

Uses

cis-Apovincamine (Vinpocetine USP Related Compound B), is a vinca alkaloid and a chemical precursor of Vinpocetine (V332500), a derivative of Vincamine with vasodilating activity. Vasodilator (cerebral).

Manufacturing Process

Apovincamine is semisynthethetic derivative of (+)-vincamine. Vincamine is alkaloid of Vinca minor. Alcoloid of Tabernaemontana rigida (Apocynaceae) also is used as raw material for preparing of apovincamine. (+)- Vincamine was transformed into oxime ester by reaction with NaNO2 in acetic acid at 0°C -(+/-)-methyl-3-((12bR)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3- a]quinolizin-1-yl)-2-(hydroxyimino)propanoate, which was resolved on the isomers with dibenzoyl D-tartratic acid. (-)-Methyl 3-((12bR)-1-ethyl- 1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-1-yl)-2- (hydroxyimino)propanoate was re-crystallized from methanol to afford (-)- methyloxime ester, MP: 195°C. 2 g of above oxime methyl ester was heated in mixture of methanol (37.5 ml) and conc. H2SO4 (13.5 ml) on water bath for 1 hour. The solution was poured into ice-water (80 ml), basified with conc. NH4OH to pH 9, and extracted with CH2Cl2 (3x20 ml). The combined extracts were dried (MgSO4), filtered, evaporated in vacuum and the residue was re-crystallized from MeOH (5 ml) to yield 1.32 g (72.5%) of (+)-apovincamine, MP: 160°-162°C.

Therapeutic Function

Vasodilator

InChI:InChI=1/C21H24N2O2/c1-3-21-10-6-11-22-12-9-15-14-7-4-5-8-16(14)23(18(15)19(21)22)17(13-21)20(24)25-2/h4-5,7-8,13,19H,3,6,9-12H2,1-2H3/t19-,21+/m1/s1

Upstream product

• 55872-13-4 (-)-criocerine 
• 3247-10-7 (-)-vincadifformine 
• 85588-92-7 (-)-methyl 1,2,3,4,6,7,12,12bα-octahydroindolo<2,3-a>quinolizine(1β-yl) pyruvate oxime 
• 70154-93-7 (-)-14-hydroxyamino-14-methoxycarbonyl-eburnan 
• 89396-77-0 3-((1S,12bS)-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 
• 6835-99-0 14-epivincamine 
• 186887-54-7 (1S,11aS,11bR)-11a-Ethyl-1-methoxy-10-methyl-1,2,4,5,11a,11b-hexahydro-3a,9b-diaza-benzo[cd]fluoranthen-3-one 
• 186887-52-5 (1S,11aS,11bS)-11a-Ethyl-1-methoxy-10-methyl-1,2,4,5,11a,11b-hexahydro-3a,9b-diaza-benzo[cd]fluoranthen-3-one 
• 186887-50-3 (11aS,11bS)-11a-Ethyl-10-methyl-4,5,11a,11b-tetrahydro-3a,9b-diaza-benzo[cd]fluoranthen-3-one 
• 186887-60-5 (11R,11aR,11bS)-11-Bromo-10-[1-bromo-meth-(E)-ylidene]-11a-ethyl-2,3,4,5,10,11,11a,11b-octahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene 
• 53412-07-0 (4¹S,13aS)-13a-ethyl-2,3,4¹,5,6,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carbaldehyde 
• 186887-58-1 (11aS,11bS)-11a-Ethyl-10-methyl-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene 
• 66113-74-4 hydroxy-16 dehydro-1 vincadifformine 
• 74947-45-8 (-)-18-iodo-criocerine 

Downstream Products

• 21019-23-8 deoxyvincamine 
• 27773-65-5 Apovincaminic acid 
• 42971-09-5 Vinpocetine 
• 21019-23-8 (3S,16S,14R)-14-deoxyvincamine 
• 21019-24-9 (3S,16S,14S)-14-deoxyvincamine 
• 23173-26-4 ((4¹S,13aS)-13a-ethyl-2,3,4¹,5,6,13a-hexahydro-1H-indolyl[3,2,1-de]pyridyl[3,2,1-ij][1,5]naphthyridine-12-yl)methanol 
• 23173-24-2 (13a-ethyl-2,3,5,6,12,13,13a,13b-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridin-12-yl)-methanol 
• 23173-27-5 (13a-ethyl-2,3,5,6,12,13,13a,13b-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridin-12-yl)-methanol 
• 95407-52-6 apovincaminic acid methyl mandelate ester 
• 65825-92-5 6-ketoapovincamine 

Relevant articles and documents

Preventing Morphine-Seeking Behavior through the Re-Engineering of Vincamine's Biological Activity

Innovative discovery strategies are essential to address the ongoing opioid epidemic in the United States. Misuse of prescription and illegal opioids (e.g., morphine, heroin) has led to major problems with addiction and overdose. We used vincamine, an indole alkaloid, as a synthetic starting point for dramatic structural alterations of its complex, fused ring system to synthesize 80 diverse compounds with intricate molecular architectures. A select series of vincamine-derived compounds were screened for both agonistic and antagonistic activities against a panel of 168 G protein-coupled receptor (GPCR) drug targets. Although vincamine was without an effect, the novel compound 4 (V2a) demonstrated antagonistic activities against hypocretin (orexin) receptor 2. When advanced to animal studies, 4 (V2a) significantly prevented acute morphine-conditioned place preference (CPP) and stress-induced reinstatement of extinguished morphine-CPP in mouse models of opioid reward and relapse. These results demonstrate that the ring distortion of vincamine offers a promising way to explore new chemical space of relevance to opioid addiction.

Pervone derivative and purpose thereof to treatment of diabetes B

The invention relates to the field of medicinal chemistry, in particular to a derivative shown as a general formula (I) and a purpose of a medicine composition containing the derivative to preparationof medicine for treating diabetes B. The compound has the effect of preventing pancreatic island beta cell apoptosis and can be used for treating the diabetes B. The general formula (I) is shown in the description.

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.