[42971-09-5] Vinpocetine AKSci J10479
 
 
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  J10479    
Vinpocetine
, 98% (HPLC)
 
Eburnamenine-14-carboxylic acid ethyl ester




IDENTITY
CAS Number:[42971-09-5]
MDL Number:MFCD00211233
MF:C22H26N2O2
MW:350.45
EINECS:256-028-0
SPECIFICATIONS & PROPERTIES
Purity:98% (HPLC)
Available Spectra:FT-IR, LCMS, HPLC
Physical Form:White powder or crystals or solid
Melting Point:147-156°C
Optical Rotation:+115.0 to +120.0° (c=2, Pyridine)
Long-Term Storage:Store long-term at 2-8°C

BIOLOGICAL INFO
Solubility:DMSO: 5mg/mL; H2O: insoluble

REVIEW

 Vinpocetine, a semisynthetic derivative of Vincamine alkaloid, extracted from the periwinkle (plant) Vinca minor, is the first full-fledged nootropic (a supplement possibly affecting the mind). Tested as a neuronal plasticity enhancer, marketed as a ''memory booster'', vinpocetine has been shown to facilitate long-term potentiation, improve spatial memory in animal models, and enhance performance on cognitive tests in humans. Vinpocetine has several pharmacological and biochemical actions, including stimulating cerebral vasodilation, increasing tolerance of cerebral tissue to hypoxic and ischemic insults, anticonvulsant activity, inhibitory effects on phosphodiesterase (PDE), improving hematological flow properties and inhibiting thrombocyte aggregation. The cognitive enhancement function of vinpocetine comes from its inhibition of PDE type 1, which leads to an increase in cAMP and cGMP levels. These cyclic nucleotides can in turn activate a series of kinases that phosphorylate the transcription factors cAMP response element binding protein (CREB) and serum response factor (SRF), leading to the expression of plasticity- related genes. Recently, it has been shown that vinpocetine inhibits IKK, preventing I-kappaB degradation and the consequent translocation of NF-kappaB to the nucleus, and is independent of vinpocetine action on PDE1. Vinpocetine also appears to provide direct neuroprotective effects under in vitro and in vivo conditions. These effects appear to be related to the inhibition of voltage-dependent neuronal sodium channels, indirect inhibition of some molecular cascades initiated by the rise of intracellular calcium levels and to a lesser extent, inhibition of adenosine reuptake. These neuroprotective effects might also be enhanced by vinpocetine 's selective inhibition of calcium calmodulin-dependent cGMP-PDE. This inhibition may enhance intracellular cGMP levels in vascular smooth muscle, leading to reduced cerebrovascular resistance and increased cerebral blood flow.

REFERENCES
[1]Patyar, Sazal; Prakash, Ajay; Modi, Manish; Medhi, Bikash: Role of Vinpocetine in cerebrovascular diseases. Pharmacological Reports (2011), 63(3), 618-628.
[2] Bereczki, D.; Fekete, I.: A systematic review of Vinpocetine therapy in acute ischemic stroke. European Journal of Clinical Pharmacology (1999), 55(5), 349-352.
[3] Medina, Alexandre E.: Vinpocetine as a potent antiinflammatory agent. Proceedings of the National Academy of Sciences of the United States of America (2010), 107(22), 9921-9922.
[4] Jeon KI, Xu X, Aizawa T, Lim JH, Jono H, Kwon DS, Abe J, Berk BC, Li JD, Yan C. Vinpocetine inhibits NF-kappaB dependent inflammation via an IKK-dependent but PDE-independent mechanism. Proc Natl Acad Sci USA (2010), 107:9795-9800.

GHS

Pictograms

Signal Word
Warning

Hazard Statements
H302

Precautionary Statements
P264; P270; P301+P312; P330; P501


Current as of April 29, 2017


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CATEGORIES

 APIs and Bioactives > Alkaloids


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