Vinpocetine
[CAS# 42971-09-5]

Identification

• Classification: API >> Circulatory system medication >> Peripheral vasodilator
• Name: Vinpocetine
• Synonyms: Ethyl (3alpha,16alpha)-eburnamenine-14-carboxylate
• Molecular Formula: C₂₂H₂₆N₂O₂
• Molecular Weight: 350.45
• CAS Registry Number: 42971-09-5
• EC Number: 256-028-0
• SMILES: CC[C@@]12CCCN3[C@@H]1C4=C(CC3)C5=CC=CC=C5N4C(=C2)C(=O)OCC

Properties

• Density: 1.3±0.1 g/cm³ Calc.^*
• Boiling point: 419.5±45.0 °C 760 mmHg (Calc.)^*
• Flash point: 207.5±28.7 °C (Calc.)^*
• Solubility: DMSO: 5 mg/mL, DMF: 3 mg/mL, ethanol,acetic acid: 50 mM, acetone:25 mg/mL (Expl.)
• Index of refraction: 1.666 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332

Discovery and Applications

Vinpocetine is a synthetic derivative of the natural alkaloid vincamine, which is extracted from the leaves of the periwinkle plant Vinca minor. Chemically known as ethyl apovincaminate, vinpocetine has the molecular formula C₂₂H₂₆N₂O₂ and features a complex indole-based structure.

Originally developed in the late 1960s and 1970s, vinpocetine was introduced primarily as a neuroprotective and nootropic agent. It has been widely used to improve cerebral blood flow, enhance brain metabolism, and support cognitive function, particularly in conditions such as stroke recovery, dementia, and age-related cognitive decline.

Pharmacologically, vinpocetine acts as a selective phosphodiesterase type 1 (PDE1) inhibitor, leading to increased cyclic nucleotide levels that facilitate vasodilation and improved cerebral microcirculation. Additionally, it modulates sodium and calcium ion channels, which can protect neurons against excitotoxicity and ischemic damage.

Vinpocetine exhibits antioxidant and anti-inflammatory properties, reducing oxidative stress and inhibiting pro-inflammatory mediators in neural tissues. These effects contribute to its potential in neurodegenerative disease management and cognitive enhancement.

Clinically, vinpocetine is employed in various countries as a prescription drug or dietary supplement for cerebrovascular disorders, tinnitus, and memory enhancement. Despite widespread use, its efficacy in some applications remains under investigation, and regulatory approvals vary by region.

Beyond neurological uses, vinpocetine has shown potential benefits in cardiovascular health and peripheral circulation. Research is ongoing to explore its broader therapeutic roles and optimize its pharmacokinetic profile.

Overall, vinpocetine represents a well-studied neuroactive compound with multifaceted mechanisms that support brain health and cognitive performance. Its continued study aims to clarify clinical benefits and safety profiles for wider medical application.

References

2020. Optimized preparation of vinpocetine micelles and in vivo evaluation of its pharmacokinetics in rats. Pharmaceutical Development and Technology, 25(1).
DOI: 10.1080/10837450.2019.1709501

2012. Chiral separation of vinpocetine using cyclodextrin-modified micellar electrokinetic chromatography. Chirality, 24(4).
DOI: 10.1002/chir.21990

2009. Preparation and Evaluation of Self-Microemulsifying Drug Delivery System Containing Vinpocetine. Drug Development and Industrial Pharmacy, 35(5).
DOI: 10.1080/03639040802488089