WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 329646
Description: Vinpocetine, also known as AY-27,255, is a synthetic derivative of the vinca alkaloid vincamine (sometimes described as "a synthetic ethyl ester of apovincamine"), an extract from the lesser periwinkle plant. Vinpocetine has been reported to have cerebral blood-flow enhancing and neuroprotective effects, and has been used as a drug in Eastern Europe for the treatment of cerebrovascular disorders and age-related memory impairment. Vinpocetine acts as a phosphodiesterase (PDE) type-1 inhibitor in isolated rabbit aorta, Independent of vinpocetine's action on PDE, vinpocetine inhibits IKK preventing IκB degradation and the following translocation of NF-κB to the cell nucleus.
MedKoo Cat#: 329646
Chemical Formula: C22H26N2O2
Exact Mass: 350.1994
Molecular Weight: 350.462
Elemental Analysis: C, 75.40; H, 7.48; N, 7.99; O, 9.13
Synonym: Vinpocetine, apovincaminic acid ethyl ester, ethyl apovincaminate, AY 27,255, AY-27,255, RGH 4405, RGH4405, RGH-4405, TCV-3B, TCV 3B, TCV3B, Cavinton, Intelectol
IUPAC/Chemical 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
InChi Key: DDNCQMVWWZOMLN-IRLDBZIGSA-N
InChi Code: 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
SMILES Code: O=C(C1=C[C@@](CCC2)(CC)[C@]3([H])N2CCC4=C3N1C5=C4C=CC=C5)OCC
Appearance: White to off-white crystalline powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 350.462 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
|Concentration / Solvent Volume / Mass||1 mg||5 mg||10 mg|
|1 mM||1.15 mL||5.76 mL||11.51 mL|
|5 mM||0.23 mL||1.15 mL||2.3 mL|
|10 mM||0.12 mL||0.58 mL||1.15 mL|
|50 mM||0.02 mL||0.12 mL||0.23 mL|
1: Feng X, Wang Y, Hao Y, Ma Q, Dai J, Liang Z, Liu Y, Li X, Song Y, Si C. Vinpocetine Inhibited the CpG Oligodeoxynucleotide-induced Immune Response in Plasmacytoid Dendritic Cells. Immunol Invest. 2017 Apr;46(3):263-273. doi: 10.1080/08820139.2016.1248561. Epub 2016 Dec 14. PubMed PMID: 27967259.
2: Sönmez MF, Ozdemir Ş, Guzel M, Kaymak E. The ameliorative effects of vinpocetine on apoptosis and HSP-70 expression in testicular torsion in rats. Biotech Histochem. 2017;92(2):92-99. doi: 10.1080/10520295.2016.1259499. Epub 2017 Feb 26. PubMed PMID: 28296551.
3: Bora S, Erdogan MA, Armagan G, Sevgili E, Dagcı T. Vinpocetine and Vasoactive Intestinal Peptide Attenuate Manganese-Induced Toxicity in NE-4C Cells. Biol Trace Elem Res. 2016 Dec;174(2):410-418. Epub 2016 May 20. Erratum in: Biol Trace Elem Res. 2017 Jan;175(1):236. PubMed PMID: 27206668.
4: Avula B, Chittiboyina AG, Sagi S, Wang YH, Wang M, Khan IA, Cohen PA. Identification and quantification of vinpocetine and picamilon in dietary supplements sold in the United States. Drug Test Anal. 2016 Mar-Apr;8(3-4):334-43. doi: 10.1002/dta.1853. Epub 2015 Oct 1. PubMed PMID: 26426301.
5: Zhang W, Huang Y, Li Y, Tan L, Nao J, Hu H, Zhang J, Li C, Kong Y, Song Y. Efficacy and Safety of Vinpocetine as Part of Treatment for Acute Cerebral Infarction: A Randomized, Open-Label, Controlled, Multicenter CAVIN (Chinese Assessment for Vinpocetine in Neurology) Trial. Clin Drug Investig. 2016 Sep;36(9):697-704. doi: 10.1007/s40261-016-0415-x. PubMed PMID: 27283947.
6: Nivison-Smith L, O'Brien BJ, Truong M, Guo CX, Kalloniatis M, Acosta ML. Vinpocetine modulates metabolic activity and function during retinal ischemia. Am J Physiol Cell Physiol. 2015 May 1;308(9):C737-49. doi: 10.1152/ajpcell.00291.2014. Epub 2015 Feb 18. PubMed PMID: 25696811.
7: Wu MP, Zhang YS, Xu X, Zhou Q, Li JD, Yan C. Vinpocetine Attenuates Pathological Cardiac Remodeling by Inhibiting Cardiac Hypertrophy and Fibrosis. Cardiovasc Drugs Ther. 2017 Mar 20. doi: 10.1007/s10557-017-6719-0. [Epub ahead of print] PubMed PMID: 28321644.
8: Shang Y, Wang L, Li Y, Gu PF. Vinpocetine Improves Scopolamine Induced Learning and Memory Dysfunction in C57 BL/6J Mice. Biol Pharm Bull. 2016 Sep 1;39(9):1412-8. doi: 10.1248/bpb.b15-00881. Epub 2016 Jun 21. PubMed PMID: 27334578.
9: Ruiz-Miyazawa KW, Pinho-Ribeiro FA, Zarpelon AC, Staurengo-Ferrari L, Silva RL, Alves-Filho JC, Cunha TM, Cunha FQ, Casagrande R, Verri WA Jr. Vinpocetine reduces lipopolysaccharide-induced inflammatory pain and neutrophil recruitment in mice by targeting oxidative stress, cytokines and NF-κB. Chem Biol Interact. 2015 Jul 25;237:9-17. doi: 10.1016/j.cbi.2015.05.007. Epub 2015 May 14. PubMed PMID: 25980587.
10: Sharma S, Deshmukh R. Vinpocetine attenuates MPTP-induced motor deficit and biochemical abnormalities in Wistar rats. Neuroscience. 2015 Feb 12;286:393-403. doi: 10.1016/j.neuroscience.2014.12.008. Epub 2014 Dec 13. PubMed PMID: 25514048.
11: Nivison-Smith L, Khoo P, Acosta ML, Kalloniatis M. Pre-treatment with vinpocetine protects against retinal ischemia. Exp Eye Res. 2017 Jan;154:126-138. doi: 10.1016/j.exer.2016.11.018. Epub 2016 Nov 27. PubMed PMID: 27899287.
12: Ruiz-Miyazawa KW, Zarpelon AC, Pinho-Ribeiro FA, Pavão-de-Souza GF, Casagrande R, Verri WA Jr. Vinpocetine reduces carrageenan-induced inflammatory hyperalgesia in mice by inhibiting oxidative stress, cytokine production and NF-κB activation in the paw and spinal cord. PLoS One. 2015 Mar 30;10(3):e0118942. doi: 10.1371/journal.pone.0118942. eCollection 2015. PubMed PMID: 25822523; PubMed Central PMCID: PMC4379066.
13: Fattori V, Borghi SM, Guazelli CFS, Giroldo AC, Crespigio J, Bussmann AJC, Coelho-Silva L, Ludwig NG, Mazzuco TL, Casagrande R, Verri WA Jr. Vinpocetine reduces diclofenac-induced acute kidney injury through inhibition of oxidative stress, apoptosis, cytokine production, and NF-κB activation in mice. Pharmacol Res. 2017 Mar 14;120:10-22. doi: 10.1016/j.phrs.2016.12.039. [Epub ahead of print] PubMed PMID: 28315429.
14: Liu RT, Wang A, To E, Gao J, Cao S, Cui JZ, Matsubara JA. Vinpocetine inhibits amyloid-beta induced activation of NF-κB, NLRP3 inflammasome and cytokine production in retinal pigment epithelial cells. Exp Eye Res. 2014 Oct;127:49-58. doi: 10.1016/j.exer.2014.07.003. Epub 2014 Jul 17. PubMed PMID: 25041941; PubMed Central PMCID: PMC4461375.
15: Wang K, Wen L, Peng W, Li H, Zhuang J, Lu Y, Liu B, Li X, Li W, Xu Y. Vinpocetine attenuates neointimal hyperplasia in diabetic rat carotid arteries after balloon injury. PLoS One. 2014 May 12;9(5):e96894. doi: 10.1371/journal.pone.0096894. eCollection 2014. PubMed PMID: 24819198; PubMed Central PMCID: PMC4018422.
16: Swart PC, Currin CB, Russell VA, Dimatelis JJ. Early ethanol exposure and vinpocetine treatment alter learning- and memory-related proteins in the rat hippocampus and prefrontal cortex. J Neurosci Res. 2017 May;95(5):1204-1215. doi: 10.1002/jnr.23894. Epub 2016 Sep 10. PubMed PMID: 27614144.
17: Zhuang J, Peng W, Li H, Lu Y, Wang K, Fan F, Li S, Xu Y. Inhibitory effects of vinpocetine on the progression of atherosclerosis are mediated by Akt/NF-κB dependent mechanisms in apoE-/- mice. PLoS One. 2013 Dec 9;8(12):e82509. doi: 10.1371/journal.pone.0082509. eCollection 2013. PubMed PMID: 24349299; PubMed Central PMCID: PMC3857260.
18: Elkady EF, Tammam MH, Mohamed AA. Development and Validation of an RP-HPLC Method for the Determination of Vinpocetine and Folic Acid in the Presence of a Vinpocetine Alkaline Degradation Product in Bulk and in Capsule Form. J AOAC Int. 2017 Jan 11. doi: 10.5740/jaoacint.16-0239. [Epub ahead of print] PubMed PMID: 28074742.
19: Nivison-Smith L, Acosta ML, Misra S, O'Brien BJ, Kalloniatis M. Vinpocetine regulates cation channel permeability of inner retinal neurons in the ischaemic retina. Neurochem Int. 2014 Jan;66:1-14. doi: 10.1016/j.neuint.2014.01.003. Epub 2014 Jan 9. PubMed PMID: 24412512.
20: Ma YY, Sun L, Chen XJ, Wang N, Yi PF, Song M, Zhang B, Wang YZ, Liang QH. Vinpocetine Attenuates the Osteoblastic Differentiation of Vascular Smooth Muscle Cells. PLoS One. 2016 Sep 2;11(9):e0162295. doi: 10.1371/journal.pone.0162295. eCollection 2016. PubMed PMID: 27589055; PubMed Central PMCID: PMC5010196.
Vinpocetine was first isolated from the plant in 1975 by the Hungarian chemist Csaba Szántay. The mass production of the synthetic compound was started in 1978 by the Hungarian pharmaceutical company Richter Gedeon.
Vinpocetine is not FDA approved in the United States for therapeutic use. The U.S. Food & Drug Administration (FDA) has ruled that vinpocetine, due to its synthetic nature and proposed therapeutic uses, was ineligible to be marketed as dietary supplement under the Federal Food, Drug, and Cosmetic Act (FDCA).