Vinpocetine
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Vinpocetine
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| Systematic (IUPAC) name | |
| (3α,16α)-Eburnamenine-14-carboxylic acid ethyl ester | |
| Identifiers | |
| CAS number | |
| ATC code | N06 |
| PubChem | |
| Chemical data | |
| Formula | C22H26N2O2 |
| Mol. mass | 350.454 g/mol |
| Pharmacokinetic data | |
| Bioavailability | 56.6 +/- 8.9% |
| Metabolism | hepatic |
| Half life | 2.54 +/- 0.48 hours |
| Excretion | renal |
| Therapeutic considerations | |
| Pregnancy cat. |
not recommended |
| Legal status |
OTC |
| Routes | oral, intravenous |
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"),[1] an extract from the periwinkle (plant) Vinca minor.
Vinpocetine is reported to have cerebral blood-flow enhancing[2] and neuroprotective effects,[3] and is used as a drug in Eastern Europe for the treatment of cerebrovascular disorders and age-related memory impairment.[4]
Vinpocetine is widely marketed as a supplement for vasodilation and as a nootropic for the improvement of memory. In other words, Vinpocetine helps support brain function such as enhancing concentration and memory by activating cerebral metabolism. There exists anecdotal report of uncomfortable adverse reactions to vinpocetine in a small subset of users. A low initial dosage is often recommended.
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[edit] Possible Nootropic Properties
A number of studies on healthy volunteers have demonstrated vinpocetine may elicit improvement on some aspects of memory. [5] [6] The degree which the nootropic effects of vinpocetine are mediated by mechanisms beyond vasodilation is currently unknown.
[edit] Use as a Vasodilator
Vinpocetine widely used in the body building community as an vasodilator. However, no studies have been conducted on the effectiveness of vinpocetine on performance enhancement during exercise.
[edit] 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.[7] 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.[8]
Vinpocetine is also a phosphodiesterase (PDE) type-1 inhibitor,[9] (with an IC50 of approximately 10-5 M.) leading to increases in intracellular levels of cyclic guanosine 3'5'-monophosphate (cGMP), an action that has been attributed to the vasorelaxant effects of vinpocetine on cerebral smooth muscle tissue.[10][11]
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.[12] Such an effect is consistent with the biogenic pharmacology of reserpine, a structural relative of vinpocetine, which depletes catecholamine levels and may cause depression as a side-effect of the cardiovascular and anti-psychotic effects.[13]
[edit] Side-effects
Side effects of vinpocetine may include indigestion, nausea, dizziness, anxiety, facial flushing, insomnia, headache, drowsiness and dry mouth. Vinpocetine may also cause a temporary drop in blood pressure. [14]
The safety of vinpocetine in pregnant women has not been evaluated.
Vinpocetine has been implicated in one case to induce agranulocytosis,[15] a condition in which granulocytyes - an important type of white blood cell, 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. [16]
Other Vinca alkaloids Vincristine and Vinblastine are powerful chemotherapeutic agents which impair formation of microtubules. This means Vinpocetine which may have similar effects needs further testing in the minds of many physicians before it should be used for any particular purpose, and the case of agranulocytosis mentioned above is very concerning from a clinician's standpoint.
[edit] Dosage
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).
[edit] External links
- Erowid Vinpocetine Vault
- Vinpocetine article from PDRhealth
- Vinpocetine for cognitive impairment and dementia - Cochrane review
[edit] References
- ^ Lörincz C, Szász K, Kisfaludy L. "The synthesis of ethyl apovincaminate." Arzneimittel-forschung 1976;26(10a):1907. PMID: 1037211.
- ^ Szilágyi G, Nagy Z, Balkay L, Boros I, Emri M, Lehel S, Márián T, Molnár T, Szakáll S, Trón L, Bereczki D, Csiba L, Fekete I, Kerényi L, Galuska L, Varga J, Bönöczk P, Vas A, Gulyás B. "Effects of vinpocetine on the redistribution of cerebral blood flow and glucose metabolism in chronic ischemic stroke patients: a PET study." Journal of Neurological Sciences 2005 Mar 15;229-230:275-84. Epub 2005 Jan 8. PMID: 15760651.
- ^ Dézsi L, Kis-Varga I, Nagy J, Komlódi Z, Kárpáti E. "[Neuroprotective effects of vinpocetine in vivo and in vitro. Apovincaminic acid derivatives as potential therapeutic tools in ischemic stroke]." Acta Pharmaceutica Hungarica 2002;72(2):84-91. 12498034
- ^ "Vinpocetine. Monograph." Alternative Medicine Review 2002 Jun;7(3):240-3, pp. 240. PMID: 12126465.
- ^ Psychopharmacological effects of vinpocetine in normal healthy volunteers [1].
- ^ Possible memory-enhancing properties of vinpocetine[2].
- ^ Sitges M, Galván E, Nekrassov V. "Vinpocetine blockade of sodium channels inhibits the rise in sodium and calcium induced by 4-aminopyridine in synaptosomes." Neurochemistry International 2005 Jun;46(7):533-40. PMID: 15843047.
- ^ Adám-Vizi V. "[Neuroprotective effect of sodium channel blockers in ischemia: the pathomechanism of early ischemic dysfunction]." Orvosi Hetilap 2000 Jun 4;141(23):1279-86. PMID: 10905082
- ^ Hagiwara M, Endo T, Hidaka H. "Effects of vinpocetine on cyclic nucleotide metabolism in vascular smooth muscle." Biochemical Pharmacology 1984 Feb 1;33(3):453-7. PMID: 6322804.
- ^ Truss MC, Uckert S, Stief CG, Forssmann WG, Jonas U. "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 1996;24(3):129-34. PMID: 8839479.
- ^ Gurkovskaia AV, Gokina NI, Buryĭ VA, Shuba MF. "[Electrophysiological analysis of the action of kavinton on the smooth muscles]." Biull Eksp Biol Med. 1987 Jan;103(1):68-71. PMID: 3801654.
- ^ Trejo F, Nekrassov V, Sitges M. "Characterization of vinpocetine effects on DA and DOPAC release in striatal isolated nerve endings." Brain Research 2001 Aug 3;909(1-2):59-67. PMID: 11478921.
- ^ Ibid.
- ^ http://altmedicine.about.com/od/herbsupplementguide/a/vinpocetine.htm
- ^ Shimizu Y, Saitoh K, Nakayama M, et al. Agranulocytosis induced by vinpocetine. Medicine Online [serial online]. Available at: http://www.priory.com/med/vinpocetine.htm. Accessed March 08, 2008.
- ^ 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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