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Vinpocetine structure

Vinpocetine
Vinpocetine, with the chemical formula C22H26N2O2 and CAS registry number 42971-09-5, is a synthetic alkaloid derived from the periwinkle plant. This compound is known for its neuroprotective and cognitive-enhancing properties, often used in dietary supplements for improving memory and cognitive function. Vinpocetine has been researched for its potential in treating cerebrovascular disorders and cognitive impairment. A calcium/calmodulin-dependent phosphodiesterase 1 (PDE1) inhibitor. It functions by enhancing cerebral blood flow and metabolism, thereby supporting brain function. Additionally, Vinpocetine exhibits antioxidant and anti-inflammatory effects, contributing to its therapeutic potential in various neurological conditions. This compound has gained attention in the field of neuroscience and pharmacology for its promising effects on brain health and cognitive performance. View more+
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1. Names and Identifiers
1.1 Name
Vinpocetine
1.2 Synonyms
(3A,16A)-EBURNAMENINE-14-CARBOXYLIC ACID ETHYL ESTER; (3α,16α)-Eburnamenine-14-carboxylic acid ethyl ester; 3A,16A-APOVINCAMINIC ACID ETHYL ESTER; CAVINTON; EBURNAMENINE; EBURNAMENINE-14-CARBOXYLIC ACID ETHYL ESTER; Eburnamenine-14-carboxylic acid, ethyl ester, (3ξ,16α)-; EINECS 256-028-0; Ethyl (3ξ,16α)-eburnamenine-14-carboxylate; ETHYL APOVINCAMIN-22-OATE; MFCD00211233; RGH-4405; VINPOCETIN;
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1.3 CAS No.
42971-09-5
1.4 CID
443955
1.5 EINECS
256-028-0
1.6 Molecular Formula
C22H26N2O2
1.7 Inchi
InChI=1S/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/t20-,22+/m1/s1
1.8 InChkey
DDNCQMVWWZOMLN-IRLDBZIGSA-N
1.9 Canonical Smiles
CCC12CCCN3C1C4=C(CC3)C5=CC=CC=C5N4C(=C2)C(=O)OCC
1.10 Isomers Smiles
CC[C@@]12CCCN3[C@@H]1C4=C(CC3)C5=CC=CC=C5N4C(=C2)C(=O)OCC
2. Properties
2.1 Solubility
DMSO: 5?mg/mL
2.2 Λmax
315nm(EtOH)(lit.)
2.3 Appearance
White Crystalline Solid
2.4 Storage
Ambient temperatures.
2.5 Color/Form
Cryst.
2.6 pKa
7.87±0.60(Predicted)
2.7 Water Solubility
35.5 [ug/mL]
2.8 Stability
Photosensitive
2.9 StorageTemp
Sealed in dry,2-8°C
3. Use and Manufacturing
3.1 Description

Vinpocetine(Cavinton; Ethyl apovincaminate) is a selective for PDE1 (IC50 = 21 μM). Also blocks voltage-gated Na+ channels.IC50 value:Target: PDE1; Na+ channel


Vinpocetine is an alkaloid. It has a role as a geroprotector.|Vinpocetine has been investigated for the treatment of Epilepsy.

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3.2 Methods of Manufacturing
in 500l of reaction kettle sequentially added 200 L of anhydrous ethanol, Reaction raw material vincamine?50 kg, Catalyst Sodium ethoxide 3.0 kg then keep the system pH at about 14 and slowly raised temperature to 70 ° C and allow to react for 3 h. Thin layer chromatography monitoring of raw materials vincamine fully reacted. As the hydrolysis reaction is completed, the product is vincamine acid and dehydrated vincamine mixture. Continue in the same reactor, stirring and cooling below 10 ° C, adjusting ph to about 12 by adding glacial acetic acid then again raise the temperature to reflux and allowed to react for 2h. TLC analysis of vincamine acid point of not more than 5percent, as dehydration reaction is completed. Obtained a product of dehydrating vincamine acid. Continue in the same reactor, stirring down 10 ° C below then the addition of acetic anhydride 14.5 and the reaction of water was generated. Then added acetic acid? to adjust pH , stirred the reaction for 1h and system pH value was about 7. Then add concentrated sulfuric acid to adjust the pH value to about 2, and then heated to 65-75 ° C and allowed to react for 6-8 h. TLC analysis of raw materials dehydrated vincamine acid intermediate reaction completed and completed as ethyl esterification reaction. The reaction system was stirred and cooled below 10 ° C, adjust the pH to about 7 by adding 30percent of sodium hydroxide solution as vinpocetine synthesis steps to complete.. The synthesis step of vincristine ethanol solution into the concentrator, concentrated under reduced pressure recovery of ethanol. Then add 200L methylene chloride and 200L water, into the extraction tank for extraction and separation, dichloromethane extraction separation twice, the organic phase, dried with anhydrous sodium sulfate. And then transferred to the mixer with a mixer to recover dichloromethane to dry, get vinca cis-crude. Then add 450L of anhydrous ethanol to dissolve, fine filter, the filtrate into the crystallization tank with a concentrator. After evaporation of 300 L of ethanol under reduced pressure, the mixture was cooled to below 10 ° C for 2 h, filtered and dried to obtain 43.2 kg of vincristine and 86.4percent by weight. HPLC detection purity of 99.3percent, the external standard method measured content of 99.5percent.Example 6 While stirring, 3.80 kg of aprichengchun amine and 46 L of anhydrous ethanol were put into a 100 L reaction kettle, Heated to ethanol reflux, until the material is basically clear, Then add ethanol sodium ethanol solution 1.45L, The reaction was stirred at reflux for 1 hour. The sample was monitored by HPLC and the reflux was stopped when the starting apache amine content was 0.659percent (less than 3percent). With tap water cooled to about 40 , all solvents were removed under reduced pressure to obtain solid, and then re-added 46L of fresh ethanol, and then heated to reflux until clear, ethanol solution of sodium ethoxide 0.35L, and then refluxed reaction 30 minute. Re-monitoring, when the raw material apricot amine content less than 0.3percent immediately end the reaction. Add ethanol 40-60L, reflux and clear. With preheated to 60-70 D40 stainless steel porous quick filter hot filtered reaction solution to remove insoluble. The filtrate was transferred to a clean and dry 100L reactor, the material will precipitate, and then defrost after steamed some of the ethanol, control the remaining amount of ethanol in the reactor 35-43L. Under stirring, after about 10-12 hours of natural cooling to cool down to near normal temperature, and then open the jacket tap water and continue stirring for 2 hours aging crystallization. The material was drained, drained, and thoroughly rinsed with 6L × 2 portions of absolute ethanol, drained and dried to collect the filter cake, which was crude vinpocetine
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3.3 Usage
A calcium/calmodulin-dependent phosphodiesterase 1 (PDE1) inhibitor
4. Safety and Handling
4.1 Safety

Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion. Experimental teratogenic and reproductive effects. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: Xn
Risk Statements: 22
22:? Harmful if swallowed?
Safety Statements: 36
36:? Wear suitable protective clothing?
WGK Germany: 3
RTECS: JW4792000

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4.2 Specification

? Vinpocetinum , with CAS number of 42971-09-5, can be called Ethyl (+)-cis-apovincaminate ; Ethyl(+)-apovincaminate ; cis-Apovincaminic acid ethylester ; Apovincaminic acid ethyl ester ; (+)-cis-Apovincaminic acid ethyl ester ; 1H-Indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine,eburnamenine-14-carboxylic acid deriv ; (+)-Apovincaminic acid ethyl ester . It is a?white crystalline solid,?Vinpocetinum (CAS NO.42971-09-5) is used as a vasodilator.

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4.3 Toxicity
LD50 in mice, rats (mg/kg): 534, 503 orally; 240, 133.8 i.p.; 58.7, 42.6 i.v. (Pálosi, Szporny), also reported as 161.2 mg/kg i.p. in mice (Cholnoky, Dmk)
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H302 Harmful if swallowed
Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

Response

P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell.

P330 Rinse mouth.

Storage

none

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum
13C NMR : Predict  
1H NMR : Predict  
Predict 1H proton NMR  
7. Synthesis Route
42971-09-5Total: 15 Synthesis Route
 
1617-90-9
1617-90-9 179 Suppliers
 
42971-09-5
42971-09-5 386 Suppliers
 
89396-73-6
89396-73-6
 
42971-09-5
42971-09-5 386 Suppliers
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8. Precursor and Product
precursor:
85588-92-7
85588-92-7
23944-42-5
23944-42-5
89396-73-6
89396-73-6
83023-42-1
83023-42-1
40163-56-2
40163-56-2
77793-33-0
77793-33-0
35226-41-6
35226-41-6
77793-34-1
77793-34-1
85647-38-7
85647-38-7
1617-90-9
1617-90-9
9. Computed Properties
10.Other Information
Usage
Specific calcium-calmodulin-dependent phosphodiesterase inhibitor
Merck
14,9991
Cerebral Vasodilator
Vinpocetine is a cerebrovascular expansion drug and has a relatively stronger function than Vincamine. It can selectively increase cerebral blood flow, enhance and improve brain oxygen supply, promote metabolism, enhance the capacity of deformation for red blood cells, reduce blood viscosity, inhibit platelet aggregation, improve tissue metabolism. Vinpocetine is mainly used in the treatment of cerebral infarction sequela, cerebral hemorrhage sequelae, cerebral arteriosclerosis, etc. It can also used in the treatment of retinal vascular sclerosis and blood vessel spasm, the elderly deafness, and dizziness.
Vinpocetine is a half synthetic Vincamine derivative, and has the similar effect with Vincamine. It has a stronger expansion function for cerebrovascular selectively. Pharmacological effects are as follows:
①Inhibit the activity of calcium dependency phosphodiesterase, increase the content of cAMP which can relax vascular smooth muscle, then relax vascular smooth muscle, and further increase cerebral blood flow.
②Enhance the capacity of deformation of red blood cells, reduce blood viscosity, inhibit platelet aggregation, and thus improve blood flow and microcirculation.
③Promote the brain tissue to absorb glucose, and promote the transformation of brain monoamine metabolism.
④Inhibit the increase of brain lactic acid during cerebral ischemia, increase the ATP content, inhibit the generation of lipid peroxide in the brain, delay the occurring of spasm caused by cerebral ischemia, have the function of improving cerebral metabolism and protecting brain.
the structural formula of vinpocetine
Figure 1 is the structural formula of vinpocetine.
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Pharmacokinetics
Vinpocetine is of high fat-solubility, easy to be absorbed by the organization, and widely distributed. It can through the blood brain barrier, mainly metabolism to Vinpocetine in the liver, and be excreted by the kidney.
Medicinal properties and Application
Vinpocetine is also called Ethyl apovincaminate, Conway, Karan and Vinpocetine. It is a kind of natural medicine extracted from small vinca flower, and belongs to the indole alkaloids. Can be synthetic now. The mechanism of its pharmacological action is to inhibit the activity of calcium dependency phosphodiesterase, increase the content of CGMP which can relax vascular smooth muscle, then relax vascular smooth muscle, and further increase cerebral blood flow; Enhance the capacity of deformation of red blood cells, reduce blood viscosity, inhibit platelet aggregation, and thus improve blood flow and microcirculation; Promote the brain tissue to absorb glucose, and promote the transformation of brain monoamine metabolism; Inhibit the increase of brain lactic acid during cerebral ischemia, increase the ATP content, increase thedegree of oxygen dissociation in hemoglobin; Increase the resistance capacity for cerebral anoxia and occurring of spasm caused by cerebral ischemia, inhibit the generation of lipid peroxide in the brain. Oral absorption effectively, reach peak at 1 h, then metabolize into Vinpocetine in the body. The half-life of plasma elimination is about 1 hour. For 4 weeks in a row, no accumulation in the body. Clinical used in cerebral infarction sequela, cerebral hemorrhage sequelae, cerebral arteriosclerosis, cerebral vasospasm, brain endarteritis caused vertigo, tinnitus, headache, dizziness, limb numbness, incontinence and other clinical manifestations, depression, anxiety, sleep disorder and other mental symptoms. Clinical experience has shown that it is effective regardless of the length of the course of the disease, and the symptom is fixed or not.
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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.
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Side Effects
Nervous system: head heavy, dizziness, occasional tiredness and side limb numbness, etc.
Digestive system: nausea, vomiting, loss of appetite, abdominal pain, diarrhea, etc.
Circulatory system: facial blushing, dizziness and other symptoms.
Blood system: white blood cells reduction.
Liver reaction: AST, ALT elevations, rare elevation of alkaline phosphatase.
Kidney reaction: blood urea nitrogen increasing.
Sometimes allergic reactions like skin rash, urticarial and pruritus may appear, then drug should be discontinued. Occasional mild lowering blood pressure, tachycardia, etc.
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Chemical Properties
White crystal powder, odourless and tasteless. Soluble in chloroform or 96% ethanol, insoluble in water. The melting point is 147-147 oC (decomposition). [α]D20+114°(C=1，pyridine). UV maximum absorption (96% ethanol): 229,275,315 nm (ε28200120, 00710). Acute toxicity LD50 in mice and rats (mg/kg): 534503 oral; 240133.8 intraperitoneal injection; 58.7, 42.6 intravenous injection.
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Usage
Cerebrovascular drug. A alkaloid extracted from apocynaceae plant, Vincamine derivatives. Selectively inhibit vascular smooth muscle calcium dependency phosphodiesterase, and increase the content of cGMP, expanse cerebral vascular, which in turn increase cerebral blood flow, improve cerebral circulation, but has little effects on the cardiovascular and blood pressure. Effectively, good tolerance, less adverse reaction. Used for dizziness, headache, memory disorders, movement disorder, aphasia, hypertensive encephalopathy, etc.. Can also be used in brain blood circulation obstacle caused by mental or neurological symptoms.
This information is edited by Xiao Nan.
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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.
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Chemical Properties
White Crystalline Solid
Uses
A calcium/calmodulin-dependent phosphodiesterase 1 (PDE1) inhibitor
Uses
A derivative of Vincamine with vasodilating activity. Vasodilator (cerebral).
Uses
calcium regulator
Uses
Gleevec metabolite, tyrosine kinase inhibitor
Biological Activity
Phosphodiesterase inhibitor, selective for PDE1 (IC 50 = 21 μ M). Also blocks voltage-gated Na + channels.
Biochem/physiol Actions
Ca2+-calmodulin-dependent phosphodiesterase I (PDE1) inhibitor.
Storage Conditions
in 500l of reaction kettle sequentially added 200 L of anhydrous ethanol, Reaction raw material vincamine?50 kg, Catalyst Sodium ethoxide 3.0 kg then keep the system pH at about 14 and slowly raised temperature to 70 ° C and allow to react for 3 h. Thin layer chromatography monitoring of raw materials vincamine fully reacted. As the hydrolysis reaction is completed, the product is vincamine acid and dehydrated vincamine mixture. Continue in the same reactor, stirring and cooling below 10 ° C, adjusting ph to about 12 by adding glacial acetic acid then again raise the temperature to reflux and allowed to react for 2h. TLC analysis of vincamine acid point of not more than 5percent, as dehydration reaction is completed. Obtained a product of dehydrating vincamine acid. Continue in the same reactor, stirring down 10 ° C below then the addition of acetic anhydride 14.5 and the reaction of water was generated. Then added acetic acid? to adjust pH , stirred the reaction for 1h and system pH value was about 7. Then add concentrated sulfuric acid to adjust the pH value to about 2, and then heated to 65-75 ° C and allowed to react for 6-8 h. TLC analysis of raw materials dehydrated vincamine acid intermediate reaction completed and completed as ethyl esterification reaction. The reaction system was stirred and cooled below 10 ° C, adjust the pH to about 7 by adding 30percent of sodium hydroxide solution as vinpocetine synthesis steps to complete.. The synthesis step of vincristine ethanol solution into the concentrator, concentrated under reduced pressure recovery of ethanol. Then add 200L methylene chloride and 200L water, into the extraction tank for extraction and separation, dichloromethane extraction separation twice, the organic phase, dried with anhydrous sodium sulfate. And then transferred to the mixer with a mixer to recover dichloromethane to dry, get vinca cis-crude. Then add 450L of anhydrous ethanol to dissolve, fine filter, the filtrate into the crystallization tank with a concentrator. After evaporation of 300 L of ethanol under reduced pressure, the mixture was cooled to below 10 ° C for 2 h, filtered and dried to obtain 43.2 kg of vincristine and 86.4percent by weight. HPLC detection purity of 99.3percent, the external standard method measured content of 99.5percent.Example 6 While stirring, 3.80 kg of aprichengchun amine and 46 L of anhydrous ethanol were put into a 100 L reaction kettle, Heated to ethanol reflux, until the material is basically clear, Then add ethanol sodium ethanol solution 1.45L, The reaction was stirred at reflux for 1 hour. The sample was monitored by HPLC and the reflux was stopped when the starting apache amine content was 0.659percent (less than 3percent). With tap water cooled to about 40 , all solvents were removed under reduced pressure to obtain solid, and then re-added 46L of fresh ethanol, and then heated to reflux until clear, ethanol solution of sodium ethoxide 0.35L, and then refluxed reaction 30 minute. Re-monitoring, when the raw material apricot amine content less than 0.3percent immediately end the reaction. Add ethanol 40-60L, reflux and clear. With preheated to 60-70 D40 stainless steel porous quick filter hot filtered reaction solution to remove insoluble. The filtrate was transferred to a clean and dry 100L reactor, the material will precipitate, and then defrost after steamed some of the ethanol, control the remaining amount of ethanol in the reactor 35-43L. Under stirring, after about 10-12 hours of natural cooling to cool down to near normal temperature, and then open the jacket tap water and continue stirring for 2 hours aging crystallization. The material was drained, drained, and thoroughly rinsed with 6L × 2 portions of absolute ethanol, drained and dried to collect the filter cake, which was crude vinpocetine
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Mesh
Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)|Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids. (See all compounds classified as Neuroprotective Agents.)|Drugs used to specifically facilitate learning or memory, particularly to prevent the cognitive deficits associated with dementias. These drugs act by a variety of mechanisms. (See all compounds classified as Nootropic Agents.)|Compounds which inhibit or antagonize the biosynthesis or actions of phosphodiesterases. (See all compounds classified as Phosphodiesterase Inhibitors.)
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12. Related Questions
Is Vinpocetine a Miracle Drug from Lesser Periwinkle?Derived from the lesser periwinkle plant, Vinpocetine is a bioactive alkaloid that has shown promising effects in treating complex conditions such as post-stroke sequelae, senile dementia, tinnitus, M..
Does Vinpocetine Have Health Benefits?Vinpocetine is a common pharmaceutical product widely used in the treatment of depression and other mental disorders. In addition to its therapeutic effects, Vinpocetine is also widely promoted for so..
What are the indications of Vinpocetine?Vinpocetine is a commonly used drug derived from plants in the Apocynaceae family. It is a alkaloid and a derivative of vincamine. It has beneficial effects on various diseases. So, what are the indic..
What is Vinpocetine and its Uses?Vinpocetine is a derivative of the indole alkaloid vincamine extracted from the periwinkle plant. It is an excellent medication for cerebrovascular diseases. Vinpocetine enhances red blood cell deform..
13. Realated Product Infomation
 
1. Names and Identifiers
2. Properties
3. Use and Manufacturing
4. Safety and Handling
5. Msds
6. NMR Spectrum
7. Synthesis Route
8. Precursor and Product
9. Computational chemical data
10. Other Information
11. Toltal 352 Suppliers
12. Related Questions
13. Realated Product Infomation
 
 
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