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Vinpocetine

Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy category	not recommended
Routes of administration	oral, intravenous
ATC code	N06BX18 (WHO)
Legal status
Legal status	In general: Over-the-counter (OTC)
Pharmacokinetic data
Bioavailability	56.6 +/- 8.9%
Metabolism	hepatic
Elimination half-life	2.54 +/- 0.48 hours
Excretion	renal
Identifiers
IUPAC name (3α,16α)-Eburnamenine-14-carboxylic acid ethyl ester
CAS Number	42971-09-5
PubChem CID	443955
ChemSpider	392007
UNII	543512OBTC
KEGG	D01371
ChEMBL	ChEMBL71752
CompTox Dashboard (EPA)	DTXSID5023740
ECHA InfoCard	100.050.917
Chemical and physical data
Formula	C22H26N2O2
Molar mass	350.454 g/mol g·mol
3D model (JSmol)	Interactive image
SMILES O=C(OCC)C=4n1c3c(c2ccccc12)CCN53(C=4)(CCC5)CC
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 Key:DDNCQMVWWZOMLN-IRLDBZIGSA-N
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Vinpocetine (brand names: Cavinton, Intelectol; chemical name: ethyl apovincaminate) is a semisynthetic derivative alkaloid of vincamine (sometimes described as "a synthetic ethyl ester of apovincamine"), an extract from the periwinkle plant.

Vinpocetine is reported to have cerebral blood-flow enhancing and neuroprotective effects, and is used as a drug in Eastern Europe for the treatment of cerebrovascular disorders and age-related memory impairment.

Vinpocetine is widely marketed as a supplement for vasodilation and as a nootropic for the improvement of memory. In other words, Vinpocetine may help support brain functions such as concentration and memory by activating cerebral metabolism. A small subset of users report uncomfortable, adverse reactions to vinpocetine. A low initial dosage is ordinarily recommended.

Vinpocetine has been identified as a potent anti-inflammatory agent that might have a potential role in the treatment of Parkinson's disease and Alzheimer’s disease.

Controlled clinical trials

As of 2003 only three controlled clinical trials had tested "older adults with memory problems," and these studies had promising results, in which a 2003 Cochrane review decided that the results were inconclusive.

Prior to 2003, a different study from 1985 had tested young, healthy adults, but this study had 12 subjects and used a short treatment period.

Use as a vasodilator

Vinpocetine is widely used in the body building community as a vasodilator. Although no studies have been conducted on the effectiveness of vinpocetine on performance enhancement during exercise, in trial both beneficial and adverse effects have been reported on body building forums.

Anti-inflammatory action

Vinpocetine has been identified as a novel anti-inflammatory agent. Vinpocetine inhibits the up-regulation of NF-κB by TNFα in various cell tests. Reverse transcription polymerase chain reaction also shows that it reduced the TNFα-induced expression of the mRNA of proinflammatory molecules such as interleukin-1 beta, monocyte chemoattractant protein-1 (MCP-1), and vascular cell adhesion molecule-1 (VCAM-1). In mice, vinpocetine reduced lipopolysaccharide inoculation induced polymorphonuclear neutrophil infiltration into the lung. Neuroinflammatory processes can result in neuronal death in Parkinson's disease (PD) and Alzheimer’s disease (AD). It has been suggested that "it would be interesting to test whether vinpocetine’s antiinflammatory properties would have a protective effect in models of neurodegenerative conditions such as AD and PD."

Mechanism of action

Vinpocetine has been shown to selectively inhibit voltage-sensitive Na+ channels, resulting in a dose-dependent decrease in evoked extracellular Ca+ ions in striatal nerve endings. The Na+ channel inhibiting properties of vinpocetine are thought to contribute to a general neuroprotective effect through blockade of excitotoxicity and attenuation of neuronal damage induced by cerebral ischemia/reperfusion.

Vinpocetine is also a phosphodiesterase (PDE) type-1 inhibitor, (with an IC₅₀ of approximately 10 M.) leading to increases in intracellular levels of cyclic guanosine 3'5'-monophosphate (cGMP), an action that causes the vasorelaxant effects of vinpocetine on cerebral smooth muscle tissue.

Independent of vinpocetine's action on PDE, vinpocetine inhibits IKK preventing IκB degradation and the following translocation of NF-κB to the cell nucleus.

Increases in neuronal levels of DOPAC, a metabolic breakdown product of dopamine, have been shown to occur in striatal isolated nerve endings as a result of exposure to vinpocetine. Such an effect is consistent with the biogenic pharmacology of reserpine, a structural relative of vinpocetine, which depletes catecholamine levels and causes depression as a side effect of the cardiovascular and anti-psychotic effects. However, this effect tends to be reversible upon cessation of Vinpocetine administration, with full remission typically occurring within 3–4 weeks.

Side effects

Vinpocetine is generally tolerated well and without many cases of adverse reaction reported. No serious side effects have been reported in any clinical trials, although none of these trials have been long-term. According to a Dr. Wollschlaeger, "a critical review of the literature has reported no adverse effects. Vinpocetine appears to be safe, without any adverse affects. The only reported side effect, in a very small number of cases, was a slightly upset stomach, which is almost always a side effect for some people taking herbs. We have not seen any adverse effects or drug-herb interactions, and it seems safe to take with other drugs, including diabetes drugs, and blood thinners like Coumadin."

The safety of vinpocetine in pregnant women has not been evaluated.

Vinpocetine has been implicated in one case to induce agranulocytosis, a condition in which granulocytes are markedly decreased. Some people have anecdotally noted that their continued use of vinpocetine reduces immune function. Commission E warned that vinpocetine reduced immune function and could cause apoptosis in the long term.

Other alkaloids extracted from the periwinkle family, including Vincristine and Vinblastine are powerful chemotherapeutic agents which impair formation of microtubules and thus growth of related cancers, intestinal epithelium and bone marrow.

Dosage

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It is recommended that first-time users ingest only 2–5 mg of vinpocetine with meals to make sure they are not hypersensitive to it. Users may then increase the dosage to 10–40 mg a day (which may, although very rarely, cause some light side effects).

External links

• Erowid Vinpocetine Vault
• Vinpocetine article from PDRhealth
• Vinpocetine for cognitive impairment and dementia - Cochrane review
• Information about Vinpocetine

References

1. Lörincz C, Szász K, Kisfaludy L (1976). "The synthesis of ethyl apovincaminate". Arzneimittel-Forschung. 26 (10a): 1907. PMID 1037211.{{cite journal}}: CS1 maint: multiple names: authors list (link)
2. Szilágyi G, Nagy Z, Balkay L; et al. (2005). "Effects of vinpocetine on the redistribution of cerebral blood flow and glucose metabolism in chronic ischemic stroke patients: a PET study". Journal of the Neurological Sciences. 229–230: 275–84. doi:10.1016/j.jns.2004.11.053. PMID 15760651. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)
3. Dézsi L, Kis-Varga I, Nagy J, Komlódi Z, Kárpáti E (2002). "". Acta Pharmaceutica Hungarica (in Hungarian). 72 (2): 84–91. PMID 12498034.{{cite journal}}: CS1 maint: multiple names: authors list (link)
4. "Vinpocetine. Monograph" (PDF). Alternative Medicine Review. 7 (3): 240–3. 2002. PMID 12126465.
5. ^ Jeon, KI; Xu, X; Aizawa, T; Lim, JH; Jono, H; Kwon, DS; Abe, J; Berk, BC; Li, JD (2010). "Vinpocetine inhibits NF-kappaB-dependent inflammation via an IKK-dependent but PDE-independent mechanism". Proceedings of the National Academy of Sciences of the United States of America. 107 (21): 9795–800. doi:10.1073/pnas.0914414107. PMC 2906898. PMID 20448200.
6. ^ Medina, AE (2010). "Vinpocetine as a potent antiinflammatory agent". Proceedings of the National Academy of Sciences of the United States of America. 107 (22): 9921–2. doi:10.1073/pnas.1005138107. PMC 2890434. PMID 20495091.
7. ^ McDaniel MA, Maier SF, Einstein GO (2003). "'Brain-specific' nutrients: a memory cure?". Nutrition. 19 (11–12): 957–75. doi:10.1016/S0899-9007(03)00024-8. PMID 14624946.{{cite journal}}: CS1 maint: multiple names: authors list (link)
8. ^ Szatmari SZ, Whitehouse PJ (2003). Szatmári, Szabolcs (ed.). "Vinpocetine for cognitive impairment and dementia". Cochrane Database of Systematic Reviews (1): CD003119. doi:10.1002/14651858.CD003119. PMID 12535455.
9. Subhan Z, Hindmarch I (1985). "Psychopharmacological effects of vinpocetine in normal healthy volunteers". European Journal of Clinical Pharmacology. 28 (5): 567–71. doi:10.1007/BF00544068. PMID 3899677.
10. Sitges M, Galván E, Nekrassov V (2005). "Vinpocetine blockade of sodium channels inhibits the rise in sodium and calcium induced by 4-aminopyridine in synaptosomes". Neurochemistry International. 46 (7): 533–40. doi:10.1016/j.neuint.2005.02.001. PMID 15843047.{{cite journal}}: CS1 maint: multiple names: authors list (link)
11. Adám-Vizi V (2000). "". Orvosi Hetilap (in Hungarian). 141 (23): 1279–86. PMID 10905082.
12. Hagiwara M, Endo T, Hidaka H (1984). "Effects of vinpocetine on cyclic nucleotide metabolism in vascular smooth muscle". Biochemical Pharmacology. 33 (3): 453–7. doi:10.1016/0006-2952(84)90240-5. PMID 6322804.{{cite journal}}: CS1 maint: multiple names: authors list (link)
13. Truss MC, Uckert S, Stief CG, Forssmann WG, Jonas U (1996). "Cyclic nucleotide phosphodiesterase (PDE) isoenzymes in the human detrusor smooth muscle. II. Effect of various PDE inhibitors on smooth muscle tone and cyclic nucleotide levels in vitro". Urological Research. 24 (3): 129–34. PMID 8839479.{{cite journal}}: CS1 maint: multiple names: authors list (link)
14. Gurkovskaia AV, Gokina NI, Buryĭ VA, Shuba MF (1987). "". Biulleten' Eksperimental'noĭ Biologii I Meditsiny (in Russian). 103 (1): 68–71. PMID 3801654.{{cite journal}}: CS1 maint: multiple names: authors list (link)
15. ^ Trejo F, Nekrassov V, Sitges M (2001). "Characterization of vinpocetine effects on DA and DOPAC release in striatal isolated nerve endings". Brain Research. 909 (1–2): 59–67. doi:10.1016/S0006-8993(01)02621-X. PMID 11478921.{{cite journal}}: CS1 maint: multiple names: authors list (link)
16. "Is Vinpocetine the Answer to Brain Fog, Cognitive and Memory Problems?". about.com. Retrieved 2011-06-30.
17. "Vinpocetine Side Effects and Warnings". foundhealth. Retrieved 2011-07-02.
18. "Is Vinpocetine the Answer to Brain Fog, Cognitive and Memory Problems?". about.com. Retrieved 2011-06-30.
19. Shimizu Y, Saitoh K, Nakayama M, et al. Agranulocytosis induced by vinpocetine. Medicine Online, Retrieved March 08, 2008.
20. The Complete German Commission E Monographs, Therapeutic Guide to Herbal Medicines, 1st ed. 1998, Integrative Medicine Communications, pub; Bk&CD-Rom edition, 1999.

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• PDE1 inhibitors
• Vasodilators
• Ethyl esters
• Nitrogen heterocycles