Buy Vinpocetine (BT-286308)

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Vinpocetine

Catalog Number: BT-286308

CAS Number: 42971-09-5

Molecular Formula: C22H26N2O2

Molecular Weight: 350.5 g/mol

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Product Introduction

Description

Vinpocetine is a synthetic alkaloid derived from the periwinkle plant, Vinca minor. It has been used as a dietary supplement and a prescription drug in several countries for its potential cognitive-enhancing and neuroprotective effects. Vinpocetine has been studied extensively for its pharmacological properties and potential therapeutic applications. This paper aims to provide a comprehensive review of the synthesis, chemical structure, biological activity, effects, applications, and future perspectives of Vinpocetine.

Properties

CAS Number

42971-09-5

Product Name

Vinpocetine

IUPAC Name

ethyl (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

Molecular Formula

C22H26N2O2

Molecular Weight

350.5 g/mol

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

InChI Key

DDNCQMVWWZOMLN-IRLDBZIGSA-N

SMILES

O=C(C1=C[C@@](CCC2)(CC)[C@]3([H])N2CCC4=C3N1C5=C4C=CC=C5)OCC

Solubility

Soluble in DMSO

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

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

Method of Synthesis or Extraction

Vinpocetine is synthesized from the alkaloid vincamine, which is extracted from the leaves of the periwinkle plant. The commonly used methods for the synthesis of Vinpocetine include the Perkin reaction, the Pictet-Spengler reaction, and the Diels-Alder reaction. The Perkin reaction is the most efficient method, with a yield of up to 80%. However, this method requires the use of toxic reagents and solvents, making it environmentally hazardous. The Pictet-Spengler reaction and the Diels-Alder reaction are less efficient, with yields ranging from 20% to 50%. These methods are safer and more environmentally friendly than the Perkin reaction.

Chemical Structure and Biological Activity

Vinpocetine has a unique chemical structure, consisting of a pyridine ring fused to a perhydroindole ring. It has been shown to have several biological activities, including vasodilation, anti-inflammatory, antioxidant, and neuroprotective effects. Vinpocetine's mechanism of action involves increasing blood flow to the brain, enhancing glucose and oxygen uptake, and modulating neurotransmitter release. It also inhibits phosphodiesterase type 1 (PDE1), leading to increased cyclic adenosine monophosphate (cAMP) levels, which play a crucial role in neuronal signaling.

Biological Effects

Vinpocetine has been shown to have several biological effects on cell function and signal transduction. It has been demonstrated to improve memory, attention, and cognitive function in animal models and humans. Vinpocetine has also been shown to have potential therapeutic effects in several neurological disorders, including Alzheimer's disease, Parkinson's disease, and stroke. However, Vinpocetine's potential toxic effects, such as hypotension, nausea, and headache, have also been reported.

Applications

Vinpocetine has several potential applications in medical, environmental, and industrial research. In medical research, Vinpocetine's role in drug development and clinical trials has been extensively studied. It has been shown to have potential therapeutic effects in several neurological disorders, and clinical trials have demonstrated its safety and efficacy. In environmental research, Vinpocetine's effects on ecosystems and its role in pollution management have been studied. Vinpocetine has been shown to have a low environmental impact and can be used as a sustainable alternative to traditional pesticides. In industrial research, Vinpocetine's use in manufacturing processes and improving product quality and efficiency has been explored. Health and safety considerations are crucial in the industrial application of Vinpocetine.

Future Perspectives and Challenges

Despite the extensive research on Vinpocetine, several limitations in its use and study remain. The lack of standardization in the preparation and dosage of Vinpocetine supplements has led to inconsistent results in clinical trials. The potential toxic effects of Vinpocetine also need to be further studied. Future research should focus on developing standardized protocols for the preparation and dosage of Vinpocetine supplements and exploring its potential therapeutic effects in other neurological disorders. The use of Vinpocetine in industrial and environmental research also needs to be further explored to maximize its potential benefits while minimizing its environmental impact.
Conclusion:
Vinpocetine is a synthetic alkaloid derived from the periwinkle plant, with potential cognitive-enhancing and neuroprotective effects. Its unique chemical structure and biological activity have been extensively studied, and it has several potential applications in medical, environmental, and industrial research. However, several limitations in its use and study remain, and future research should focus on developing standardized protocols and exploring its potential therapeutic effects in other neurological disorders. Vinpocetine's potential benefits and challenges should be carefully considered in its application in scientific research.

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