Chemistry:Vinpocetine

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Short description: Chemical compound
Vinpocetine
Vinpocetine.svg
Vinpocetine ball-and-stick.png
Clinical data
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
  • Not recommended[1]
Routes of
administration		Oral, intravenous
ATC code
Legal status
Legal status
  • US: Unapproved "New Drug" (as defined by 21 U.S. Code § 321(p)(1)). Use in dietary supplements, food, or medicine is unlawful; otherwise uncontrolled. [2]
  • EU: Rx-only [citation needed]
Pharmacokinetic data
Bioavailability56.6 ± 8.9%
Metabolismhepatic
Elimination half-life2.54 ± 0.48 hours
Excretionrenal
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC22H26N2O2
Molar mass350.462 g·mol−1
3D model (JSmol)
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Vinpocetine (ethyl apovincaminate) is a synthetic derivative of the vinca alkaloid vincamine, differing by the removal of a hydroxyl group. Vincamine is extracted from either the seeds of Voacanga africana or the leaves of Vinca minor (lesser periwinkle).

Medical uses

Vinpocetine has been used in many Asian and European countries for treatment of cerebrovascular disorders such as stroke and dementia for over three decades.[3]

The FDA has tentatively ruled that vinpocetine, due to its synthetic nature and proposed therapeutic uses, is ineligible to be marketed as dietary supplement under the Federal Food, Drug, and Cosmetic Act.[4][5][6][7] Despite this, vinpocetine remains widely available in dietary supplements often marketed as nootropics.[8][9][10][11]

Vinpocetine does not fully support a benefit in either dementia or stroke.[12][9][13] As of 2003, three controlled clinical trials had tested "older adults with memory problems".[14]

Side effects

Use during pregnancy may harm the baby or result in miscarriage.[1]

Adverse effects of vinpocetine include flushing, nausea, dizziness, dry mouth, transient hypo- and hyper-tension, headaches, heartburn, and decreased blood pressure.[8][15] FDA issued a statement in 2019 warning that "vinpocetine may cause a miscarriage or harm fetal development".[16]

Mechanism of action

Vinpocetine’s mechanism of action has been postulated to involve three potential effects: blockage of sodium channels, reduction of cellular calcium influx, and antioxidant activity.[13] Studies have also suggested that vinpocetine can inhibit PDE-1 in isolated rabbit aorta;[17] inhibit IKK in vitro, preventing IκB degradation and the following translocation of NF-κB to the cell nucleus;[18][19] and increase DOPAC, a metabolic breakdown product of dopamine, in isolated striatal nerve endings of rats.[20]

Dietary supplement

The inclusion of vinpocetine in dietary supplements in the U.S. has come under scrutiny due to the lack of defined dosage parameters, unproven short- and long-term benefits, and risks to human health.[21] In the U.S., vinpocetine supplements are marketed as sports supplements, brain enhancers, and weight loss supplements.[9]

A 2015 analysis of 23 brands of vinpocetine dietary supplements sold at GNC and Vitamin Shoppe retail stores reported widespread labeling errors.[4] Only 6 of the 23 supplement labels (26%) provided consumers with accurate dosages of vinpocetine (ranging from 0.3 to 32 mg per recommended daily serving), while 6 of 23 (26%) contained no vinpocetine at all, despite their labels claiming that the ingredient was in them.[9][8] In total, 9 of the 23 products tested were mislabeled, and 17 of 23 (74%) did not provide any information on the quantity of vinpocetine.[8]

In response to the study, then-senator Claire McCaskill, while at the time serving as the top Democrat on the Senate Special Committee on Aging, urged the FDA to suspend sales of vinpocetine supplements and asked 10 retailers to voluntarily stop selling vinpocetine products. McCaskill stated: "The way we regulate these supplements isn’t working—and it’s putting the lives and well-being of consumers at risk. We’ve seen products with false labels, tainted ingredients, wildly illegal claims, and, now, products containing synthesized ingredients that are classified as prescription drugs in other countries."[11]

Lawsuits

Procera AVH is a dietary supplement containing undisclosed amounts of vinpocetine in combination with huperzine A and acetyl-l-carnitine.[22][23] In 2012, manufacturer Brain Research Labs (BRL) agreed to pay $500,000 to settle a class action lawsuit which alleged that the company had falsely marketed Procera AVH as capable of improving brain function, in violation of the Consumer Fraud Act.[24]

In July 2015, the U.S. Federal Trade Commission (FTC) ruled that marketing claims for Procera AVH, which promoted the product as a “solution” to memory loss and cognitive decline, were false, misleading, unsubstantiated, and in violation of the FTC Act.[24][10][25][26] BRL and its affiliated companies Brain Power Partners, Brain Power Founders, and MedHealth Direct (all based in Laguna Beach, California) were fined $91 million. KeyView Labs, the Tampa, Florida-based company that purchased BRL in 2012, was fined $61 million.[24][25][10][26] Also named in the FTC complaint were George Reynolds (aka Josh Reynolds), founder and chief science officer of BRL, and John Arnold, the sole officer and employee of MedHealth. The FTC complaint charged Reynolds with making deceptive expert endorsements for Procera AVH.[22][24][25][10][26] The defendants in the case ultimately agreed to pay $1.4 million to settle the allegations of deceptive advertising brought by the FTC and California law enforcement officials. In addition, a permanent injunction barred the defendants from making similar deceptive claims about Procera AVH in the future and from misrepresenting the existence, results, or conclusions of any scientific study.[25][10]

References

  1. ↑ 1.0 1.1 Office of the Commissioner (3 June 2019). "Statement on warning for women of childbearing age about possible safety risks of dietary supplements containing vinpocetine" (in en). https://www.fda.gov/news-events/press-announcements/statement-warning-women-childbearing-age-about-possible-safety-risks-dietary-supplements-containing. 
  2. ↑ "Vinpocetine in Dietary Supplements". February 22, 2023. https://www.fda.gov/food/dietary-supplement-ingredient-directory/vinpocetine-dietary-supplements. 
  3. ↑ "An update on vinpocetine: New discoveries and clinical implications". European Journal of Pharmacology 819: 30–34. January 2018. doi:10.1016/j.ejphar.2017.11.041. PMID 29183836. 
  4. ↑ 4.0 4.1 "Marketers exploit the aged with unproven brain-health claims". Newsweek. January 12, 2017. http://www.newsweek.com/marketers-exploit-aged-unproven-brain-health-claims-541709?rx=us. Retrieved January 18, 2016. 
  5. ↑ "FDA rules vinpocetine not a legal dietary ingredient despite successful NDI filings". William Reed Business Media, England. http://www.nutraingredients-usa.com/Regulation/FDA-rules-vinpocetine-not-a-legal-dietary-ingredient-despite-successful-NDI-filings. 
  6. ↑ "FDA Concludes Vinpocetine Ineligible as a Dietary Ingredient". Rodman Media. September 20, 2016. http://www.nutraceuticalsworld.com/contents/view_online-exclusives/2016-09-20/fda-concludes-vinpocetine-ineligible-as-a-dietary-ingredient. 
  7. ↑ "Dubious doses". Newsweek. February 3, 2017. https://www.pressreader.com/usa/newsweek/20170203/282071981620035. Retrieved September 24, 2017. 
  8. ↑ 8.0 8.1 8.2 8.3 "Identification and quantification of vinpocetine and picamilon in dietary supplements sold in the United States". Drug Testing and Analysis 8 (3-4): 334–343. March 2016. doi:10.1002/dta.1853. PMID 26426301. 
  9. ↑ 9.0 9.1 9.2 9.3 "Vinpocetine: An Unapproved Drug Sold as a Dietary Supplement". Mayo Clinic Proceedings 90 (10): 1455. October 2015. doi:10.1016/j.mayocp.2015.07.008. PMID 26434971. 
  10. ↑ 10.0 10.1 10.2 10.3 10.4 "Supplement Marketers Will Relinquish $1.4 Million to Settle FTC Deceptive Advertising Charges". U.S. Federal Trade Commission. July 8, 2015. https://www.ftc.gov/news-events/press-releases/2015/07/supplement-marketers-will-relinquish-14-million-settle-ftc. 
  11. ↑ 11.0 11.1 "Vinpocetine: drug or dietary supplement?". Chemical & Engineering News 94 (43): 16–17. October 31, 2016. ISSN 0009-2347. https://cen.acs.org/content/cen/articles/94/i43/Vinpocetine-drug-dietary-supplement.html. Retrieved December 28, 2018. 
  12. ↑ "Vinpocetine for cognitive impairment and dementia". The Cochrane Database of Systematic Reviews 2003 (1): CD003119. 2003. doi:10.1002/14651858.CD003119. PMID 12535455. 
  13. ↑ 13.0 13.1 "Vinpocetine for acute ischaemic stroke". The Cochrane Database of Systematic Reviews 2008 (1): CD000480. January 2008. doi:10.1002/14651858.CD000480.pub2. PMID 18253980. 
  14. ↑ ""Brain-specific" nutrients: a memory cure?". Nutrition 19 (11-12): 957–975. 2003. doi:10.1016/S0899-9007(03)00024-8. PMID 14624946. 
  15. ↑ "Chemical Information Review Document for Vinpocetine (CAS No. 42971-09-5)". U.S. Department of Health and Human Services. September 2013. https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/vinpocetine091613_508.pdf. 
  16. ↑ Office of the Commissioner (2019-06-03). "Statement on warning for women of childbearing age about possible safety risks of dietary supplements containing vinpocetine" (in en). https://www.fda.gov/news-events/press-announcements/statement-warning-women-childbearing-age-about-possible-safety-risks-dietary-supplements-containing. 
  17. ↑ "Effects of vinpocetine on cyclic nucleotide metabolism in vascular smooth muscle". Biochemical Pharmacology 33 (3): 453–457. February 1984. doi:10.1016/0006-2952(84)90240-5. PMID 6322804. 
  18. ↑ "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): 9795–9800. May 2010. doi:10.1073/pnas.0914414107. PMID 20448200. 
  19. ↑ "Vinpocetine as a potent antiinflammatory agent". Proceedings of the National Academy of Sciences of the United States of America 107 (22): 9921–9922. June 2010. doi:10.1073/pnas.1005138107. PMID 20495091. Bibcode: 2010PNAS..107.9921M. 
  20. ↑ "Characterization of vinpocetine effects on DA and DOPAC release in striatal isolated nerve endings". Brain Research 909 (1-2): 59–67. August 2001. doi:10.1016/S0006-8993(01)02621-X. PMID 11478921. 
  21. ↑ "Quantitative Determination of Vinpocetine in Dietary Supplements". Natural Product Communications 11 (5): 607–609. May 2016. PMID 27319129. 
  22. ↑ 22.0 22.1 "Tampa diet supplement firm pays $1.4 million settlement over 'brain power' pill claims". Tampa Bay Times. July 9, 2015. https://www.tampabay.com/news/health/tampa-distributor-related-companies-face-14-million-penalty-for-brain/2236830. 
  23. ↑ "Procera AVH: A Pill to Restore Memory". September 18, 2012. https://sciencebasedmedicine.org/procera-avh-a-pill-to-restore-memory/. 
  24. ↑ 24.0 24.1 24.2 24.3 "False claims for brain supplement draw $152 million penalty from FTC". Orange County Register. July 6, 2015. https://www.ocregister.com/2015/07/06/false-claims-for-brain-supplement-draw-152-million-penalty-from-ftc/. 
  25. ↑ 25.0 25.1 25.2 25.3 "Procera AVH Marketers Can Forget About Claiming to Reverse Memory Loss". National Law Review. July 30, 2015. https://www.natlawreview.com/article/procera-avh-marketers-can-forget-about-claiming-to-reverse-memory-loss. Retrieved 1 January 2019. 
  26. ↑ 26.0 26.1 26.2 "Memory Supplement Marketers Settle FTC Case for $150M". July 8, 2015. https://www.naturalproductsinsider.com/claims/memory-supplement-marketers-settle-ftc-case-150m. 



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