Vinpocetine

Base Information

• Chemical Name: Vinpocetine
• CAS No.: 42971-09-5
• Deprecated CAS: 80038-06-8,115986-87-3
• Molecular Formula: C22H26N2O2
• Molecular Weight: 350.461
• Hs Code.: 29399990
• European Community (EC) Number: 256-028-0
• NSC Number: 760093
• UNII: 543512OBTC
• DSSTox Substance ID: DTXSID5023740
• Nikkaji Number: J3.510F
• Wikipedia: Vinpocetine
• Wikidata: Q420288
• NCI Thesaurus Code: C152887
• Pharos Ligand ID: 2LCK2XFY894F
• Metabolomics Workbench ID: 153177
• ChEMBL ID: CHEMBL71752
• Mol file: 42971-09-5.mol

Synonyms:Cavinton;ethyl apovincaminate;ethyl apovincaminate tartrate (1:1);ethyl apovincaminate, (+-)-isomer;ethyl apovincaminate, (16alpha)-isomer;ethyl apovincaminate, (3alpha,16alpha)-isomer;ethyl apovincaminate, 2-oxopentanedioate (1:1);ethyl apovincaminate, 3H-labeled;Kavinton;RGH-4405;TCV-3B;vinpocetine

Chemical Property of Vinpocetine

Chemical Property:

• Appearance/Colour: White crystalline solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 147-153 °C dec
• Refractive Index: 1.6500 (estimate)
• Boiling Point: 419.5 °C at 760 mmHg
• PKA: 7.87±0.60(Predicted)
• Flash Point: 207.5 °C
• PSA: 34.47000
• Density: 1.28 g/cm³
• LogP: 4.08620
• Storage Temp.: Store at RT
• Solubility.: DMSO: 5 mg/mL
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 350.199428076
• Heavy Atom Count: 26
• Complexity: 617

Purity/Quality:

99%, ^*data from raw suppliers

Vinpocetine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC12CCCN3C1C4=C(CC3)C5=CC=CC=C5N4C(=C2)C(=O)OCC
• Isomeric SMILES: CC[C@@]12CCCN3[C@@H]1C4=C(CC3)C5=CC=CC=C5N4C(=C2)C(=O)OCC
• Recent ClinicalTrials: Cognitive Effects of Vinpocetine in Healthy Adults and Patients With Epilepsy
• Recent EU Clinical Trials: Single center, exploratoric, open-label study to investigate the add-on effect of vinpocetin to the haemorheological effect of 100 mg acetyl-salicylicum in patients with chronic cerebrovascular disease
• Indications: 1.Neurology: all kinds of cerebrovascular disease and its sequelae. 2.Cardiology: coronary heart disease, hardening of the arteries and blood clotting abnormalities, etc. 3.Eye: all kinds of views of visual impairment caused by poor circulation, etc. 4.Otolaryngology: hearing loss, tinnitus, vestibular dysfunction, etc. 5.Neurosurgery: all kinds of craniocerebral surgery back function rehabilitation.
• Production Method: Vincamine extracted from small periwinkle (Vinca mino) of apocynaceae plant as raw material, dehydration to Apovincamine, then hydrolysis to Apovincaminic acid. Dissolved the acid (1.0 g, 0.003 mo1) and 1.0 g of potassium hydroxide in 80 ml of drying ethanol, add bromine ethane (0.4 g, 0.0036 mol), reflux 3 h. After the completion of reaction, cooling, evaporation to dry. Dissolve the leftovers in 500 ml of 2% sulfuric acid, and adjust the Ph to 8. Extracted with methylene chloride, drying with potassium carbonate, after the majority of methylene chloride has been evaporated, add in ethanol. Be placed overnight At 0 oC, filter the collected precipitation crystallization, washing with cold ethanol, drying, 0.66 g of Vinpocetine could be obtained. Tabersonine extracted from apocynaceae plant willow small licorice leaf or periwinkle seed can also be as raw material, through multi-step synthesis.
• Description: Vinpocetine (42971-09-5) is a phosphodiesterase PDE1 inhibitor (IC50=21 μM).1?Also blocks voltage-gated Na+?channels, IC50=44.2 μM (potency similar to phenytoin), a mechanism which may contribute to its neuroprotective and anticonvulsant activity.2?It reduces inflammatory IL-1β and TNF-α expression in rat hippocampus.3?Displays beneficial effects in a rat model of cerebral ischemia-reperfusion injury.4?Vinpocetine exerts neuroprotective effects by suppressing microglial inflammation.5
• Uses: A calcium/calmodulin-dependent phosphodiesterase 1 (PDE1) inhibitor A derivative of Vincamine with vasodilating activity. Vasodilator (cerebral). calcium regulator Gleevec metabolite, tyrosine kinase inhibitor

Technology Process of Vinpocetine

There total 44 articles about Vinpocetine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

ethanol (64-17-5) + apovincamine (4880-92-6) → Vinpocetine (42971-09-5,80038-06-8)

Guidance literature:

With titanium(IV) tetraethanolate; In 1,4-dioxane; for 40h; Heating;

DOI:10.1080/00397919408011297

Reference yield: 90.0%

sodium ethanolate (141-52-6) + apovincamine (4880-92-6) → Vinpocetine (42971-09-5,80038-06-8)

Guidance literature:

In ethanol; toluene; for 0.0166667h; Heating;

Reference yield: 83.0%

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 ethyl ester (89396-73-6) → Vinpocetine (42971-09-5,80038-06-8)

Guidance literature:

In ethanol; sulfuric acid; for 0.5h; Heating;

DOI:10.1016/S0040-4020(01)88614-2

upstream raw materials:

ethanol

(3S,17S)-14-oxo-15-hydroxyimino-E-homoeburnane

vincamin

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 ethyl ester

Downstream raw materials:

(+)-apovincaminic acid N-oxide ethyl ester

Apovincaminic acid

14,15-dihydro-14β-hydroxy-(3α,16α)-eburnamenine-14-carboxylic acid ethyl ester

vinburnine

Refernces

• 1、 -. "Preparation method of vinpocetine". Paragraph 0051; 0055-0058; 0061-0064; 0067-0070; 0073-0086. . Retrieved 2021/04/10.
• 2、 -. "A semi-synthetic synthesis process of vinpocetine". Paragraph 0012; 0013. . Retrieved 2017/03/14.