Is Angelo Lisi’s “Studies of methylhexaneamine in supplements and geranium oil” the WEAKEST Study Ever Published?

This is part five of a six page series researching whether DMAA (1,3 dimethylamylamine) is a natural constituent of geranium flowers. All six parts are linked from our main DMAA Geranium page.

Angelo Lisi Australia DMAA Geranium Study

Regardless of what side of the DMAA argument you are on, you cannot possibly take this paper seriously.

In our previous article, we explored how the FDA wasted $2.3 million dollars on a study where researchers Mahmoud ElSohly and Ikhlas Khan did not publish their complete findings. While their failure to disclose the minute amounts of DMAA they found in geranium was not as egregious as Daniel Armstrong’s DMAA Debacle, it was funded by American taxpayers, adding another layer of crookedness to the entire debate on DMAA.

But it’s not just the Americans who were robbed by their government — the Australians got in the act as well. And in this case, there wasn’t even an attempt to make it look like a legitimate study.

In 2011, the Australian Government paid for their own DMAA study through the Anti-Doping Research Program of the Department of Prime Minister.

Sound familiar?

Well here we go again.

Was Angelo Lisi’s government-funded Geranium ‘study’ the most half-assed research ever performed?

Angelo Lisi, an Australian government employee (given his email address shown on Wiley’s site[45]) published a paper that tested five commercially available geranium oils and determined that “These studies as well as closer scrutiny of the original publication by Ping et al. show that geranium oils do not contain methylhexaneamine”.

Conveniently, the geranium oils were from Egypt, France, and New Zealand — not China — so we find it quite telling that they are trying to throw Ping under the bus while not even attempting to replicate his work or his source materials.

Used a known-inferior extraction method

Even more convenient, three of these five samples used steam distillation methodology to extract the geranium, even though the paper itself states that

“It should be noted that methylhexaneamine is a volatile substance and is likely to have been lost through a steam distillation extraction, so cold-pressed material had the best chance of retaining this compound”

Yet with the above knowledge in mind, they still used this extraction method on the majority of samples in the study! Why in the hell would you do that if you were really trying to discover the truth?

And why would you use different techniques on different oils? Shouldn’t there be standards involved? Shouldn’t you use the same method(s) on every sample?

Was DMAA still discovered and not published?

What’s even wilder is that even with the above extraction methodology, some researchers argue that 1,3 Dimethylamylamine was still found in this study. Thomas Gauthier states this in his paper “Evidence for the Presence of 1,3-Dimethylamylamine (1,3-DMAA) in Geranium Plant Materials”, published in Analytical Chemistry Insights:[18]

Separation of the 1,3-DMAA derivative was performed using an Agilent HP Ultra 2 column. Semi-quantitative analysis was based on selected ion monitoring at m/z 238. Separation of both 1,3-DMAA diastereomers was achieved using this method, although the authors incorrectly refer to the two peaks as representing enantiomers.

The authors report that 1,3-DMAA was not found in any of the five geranium oils, however no detection limits were reported and no standard concentrations or calibration data are presented.[18]

Angelo Lisi  DMAA Geranium Enantiometer vs Diastereomers

The section and chart in question by Gauthier. Why did Lisi gloss over this enantiometer finding so briefly? Are you sure those aren’t actually diastereomers?

So what Gauthier is implying is that Lisi did find two peaks in the geranium oil that correspond to real deal DMAA, yet they were “mislabeled” as enantiomers… thus allowing for the claim that there’s no DMAA. But who’s right?

Objections to this study:

Given the

  • Politically-driven source of funding,
  • Lack of detection limits,
  • Vacancy of research data, standardizations, and calibration data
  • Usage of a known-ineffective extraction technique,
  • Acquisition of oils from obscure parts of the world not in dispute, and
  • Finding and potential mislabeling of DMAA’s diastereomers as enantiomers,

this “study” is one giant shameful turd that should never be taken seriously, no matter what side of the DMAA argument you are on.

Yet with all that said, there’s still a very serious chance that even these non-Chinese geranium oils contained the compound!

At least with the original USADA-funded DMAA ‘study’ (also by Khan and ElSohly), taxpayers likely didn’t foot much (or any) of the bill. Australians couldn’t be so lucky in this situation, but then again, at least they didn’t get scammed for $2.3 million either.

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References

The following is a list of references from all sources cited in this entire series of articles:

  1. Ping Z, Jun Q, Qing L; “A study on the chemical constituents of geranium oil” (with corrections); Guizhou Inst Technol 25(1):82-85; 1996;  https://blog.priceplow.com/wp-content/uploads/hi-tech-vs-fda-20161230-wenik-exhibit-53-ping-study-translated.pdf
  2. Ping Z, Jun Q, Qing L; “A study on the chemical constituents of geranium oil” (with original parts); Guizhou Inst Technol 25(1):82-85; 1996; https://blog.priceplow.com/wp-content/uploads/ping-chemical-constituents-of-geranium-oil-1996-original-parts.pdf
  3. USPLabs; “First Response Letter to Warning Letter No. 285519”; May 15, 2012; https://blog.priceplow.com/wp-content/uploads/usplabs-fda-warning-letter-response-1-20120515.pdf
  4. Hi-Tech Pharmaceuticals; Exhibit 6: Email from Robert Moore to Amy Eichner; November 29, 2010; https://blog.priceplow.com/wp-content/uploads/hi-tech-vs-fda-20161230-wenik-exhibit-06-robert-moore-fda-email-geranium-dmaa.pdf
  5. Thomas, Jennifer A; “Response Letter to USP Labs LLC Concerning DMAA”; Division of Enforcement, Office of Compliance, Center for Food Safety and Applied Nutrition, Food and Drug Administration; April 18, 2013; https://www.fda.gov/AboutFDA/CentersOffices/OfficeofFoods/CFSAN/CFSANFOIAElectronicReadingRoom/ucm350199.htm
  6. Li, J.S., M. Chen, and Z.C. Li. “Identification and Quantification of Dimethylamylamine in Geranium by Liquid Chromatography Tandem Mass Spectrometry.” Analytical Chemistry Insights 7 (2012): 47–58; https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3422085/
  7. Fleming, Heather L., Patricia L. Ranaivo, and Paul S. Simone. “Analysis and Confirmation of 1,3-DMAA and 1,4-DMAA in Geranium Plants Using High Performance Liquid Chromatography with Tandem Mass Spectrometry at Ng/g Concentrations.” Analytical Chemistry Insights 7 (2012): 59–78; https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3512447/
  8. Roosevelt, Michael W; “Warning Letter to USPLabs”; Office of Compliance, Center for Food Safety and Applied Nutrition, Food and Drug Administration; April 24, 2012; https://www.fda.gov/ICECI/EnforcementActions/WarningLetters/2012/ucm302167.htm
  9. Mahmoud A. ElSohly, Waseem Gul, Kareem M. ElSohly, Timothy P. Murphy, Aroona Weerasooriya, Amar G. Chittiboyina, Bharathi Avula, Ikhlas Khan, Amy Eichner, Larry D Bowers; “Pelargonium Oil and Methyl Hexaneamine (MHA): Analytical Approaches Supporting the Absence of MHA in Authenticated Pelargonium graveolens Plant Material and Oil”; J Anal Toxicol (2012) 36 (7): 457-471; June 25, 2012; https://academic.oup.com/jat/article/36/7/457/828772/Pelargonium-Oil-and-Methyl-Hexaneamine-MHA (PDF available at https://blog.priceplow.com/wp-content/uploads/study-where-dmaa-was-detected-in-the-ppb-range-but-not-published-with-that-information-20120625.pdf)
  10. Hi-Tech Pharmaceuticals; “Statement of Undisputed Material Facts”; Hi-Tech Pharmaceuticals vs. FDA; December 30, 2016; https://blog.priceplow.com/wp-content/uploads/hi-tech-vs-fda-20161230-hi-tech-pharma-statement-of-undisputed-material-facts.pdf
  11. Hi-Tech Pharmaceuticals; Exhibit 8: Email Correspondence Between Amy Eichner (USADA – US Anti Doping Agency), Dan Fabricant (FDA), ; April 13, 2011; https://blog.priceplow.com/wp-content/uploads/hi-tech-vs-fda-20161230-wenik-exhibit-08-amy-eichner-dan-fabricant-robert-moore-email.pdf
  12. Hi-Tech Pharmaceuticals; Exhibit 12: Consulting Contract Between Mahmoud ElSohly (Phytochemical Services Incorporated) and Amy Eichner (USADA – US Anti Doping Agency); April 22, 2011; https://blog.priceplow.com/wp-content/uploads/hi-tech-vs-fda-20161230-wenik-exhibit-12-amy-eichner-elsohly-email-consulting-contract.pdf
  13. Hi-Tech Pharmaceuticals; Exhibit 4: Deposition of Amy Eichner (USADA – US Anti Doping Agency); December 14, 2016; https://blog.priceplow.com/wp-content/uploads/hi-tech-vs-fda-20161230-wenik-exhibit-04-amy-eichner-deposition.pdf
  14. Hi-Tech Pharmaceuticals; Exhibit 11: Deposition of Ikhlas Khan; October 26, 2016; https://blog.priceplow.com/wp-content/uploads/hi-tech-vs-fda-20161230-wenik-exhibit-11-ikhlas-khan-deposition-20161026.pdf
  15. Hi-Tech Pharmaceuticals; Exhibit 9; Email Correspondence between Amy Eichner (USADA – US Anti Doping Agency) and Dan Levy (NSF); December 1, 2010; https://blog.priceplow.com/wp-content/uploads/hi-tech-vs-fda-20161230-wenik-exhibit-09-amy-eichner-dan_levy-NSF-email-20101201.pdf
  16. Hi-Tech Pharmaceuticals; Exhibit 13; Email Correspondence between Mahmood ElSohly, Amy Eichner (USADA – US Anti Doping Agency), Larry Bowers (USADA), Ikhlas Khan, and Waseem Gul; May 27, 2011; https://blog.priceplow.com/wp-content/uploads/hi-tech-vs-fda-20161230-wenik-exhibit-13-mahmood-elsohly-finds-dmaa-in-geranium-emails-20110527.pdf
  17. Hi-Tech Pharmaceuticals; Exhibit 14; Email Correspondence between Mahmood ElSohly, Amy Eichner (USADA – US Anti Doping Agency), Larry Bowers (USADA), Ikhlas Khan, and Waseem Gul; https://blog.priceplow.com/wp-content/uploads/hi-tech-vs-fda-20161230-wenik-exhibit-14-mahmood-el-sohly-change-dmaa-detection-limits-20110601.pdf
  18. Gauthier, Thomas D. “Evidence for the Presence of 1,3-Dimethylamylamine (1,3-DMAA) in Geranium Plant Materials.” Analytical Chemistry Insights 8 (2013): 29–40; https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3682735/
  19. Ying Zhang, Ross M. Woods, Zachary S. Breitbach, Daniel W. Armstrong; “1,3-Dimethylamylamine (DMAA) in supplements and geranium products: natural or synthetic?”; Drug Testing and Analysis; Volume 4, Issue 12, pages 986–990; December 2012; http://onlinelibrary.wiley.com/doi/10.1002/dta.1368/abstract (full-text available at next citation)
  20. Hi-Tech Pharmaceuticals; Exhibit 18; Ying Zhang, Ross M. Woods, Zachary S. Breitbach, Daniel W. Armstrong; “1,3-Dimethylamylamine (DMAA) in supplements and geranium products: natural or synthetic?” – Published version with Markup; Drug Testing and Analysis; Volume 4, Issue 12, pages 986–990; December 2012; https://blog.priceplow.com/wp-content/uploads/hi-tech-vs-fda-20161230-wenik-exhibit-18-daniel_armstrong_study-published-version-marked.pdf
  21. Hi-Tech Pharmaceuticals; Exhibit 17; Ying Zhang, Ross M. Woods, Zachary S. Breitbach, Daniel W. Armstrong; “1,3-Dimethylamylamine (DMAA) in supplements and geranium products: natural or synthetic?” – UNPUBLISHED version; https://blog.priceplow.com/wp-content/uploads/hi-tech-vs-fda-20161230-wenik-exhibit-17-daniel_armstrong_study-unpublished-version-unmarked.pdf
  22. Hi-Tech Pharmaceuticals; Exhibit 17; Ying Zhang, Ross M. Woods, Zachary S. Breitbach, Daniel W. Armstrong; “1,3-Dimethylamylamine (DMAA) in supplements and geranium products: natural or synthetic?” – UNPUBLISHED version with markup; https://blog.priceplow.com/wp-content/uploads/hi-tech-vs-fda-20161230-wenik-exhibit-17-daniel_armstrong_study-unpublished-version-marked.pdf
  23. Unverified Unpublished Supplementary Materials in “1,3-Dimethylamylamine (DMAA) in supplements and geranium products: natural or synthetic?”; https://blog.priceplow.com/wp-content/uploads/armstrong-dmaa-study-original_supplementary_materials.docx
  24. Cawley, Adam; John Wiley & Sons Ltd; “Special Issue: Stable isotope ratio analysis in sports anti-doping”; December 2012; Volume 4, Issue 12; Pages 891–1039; http://onlinelibrary.wiley.com/doi/10.1002/dta.v4.12/issuetoc
  25. Watson, Elaine; “USPLabs promises new data that ‘definitively’ proves presence of DMAA in geranium”; NutraIngredients-USA.com; July 16, 2012; http://www.nutraingredients-usa.com/Research/USPLabs-promises-new-data-that-definitively-proves-presence-of-DMAA-in-geranium
  26. Hi-Tech Pharmaceuticals; Exhibit 16; Deposition of Cara Welch (FDA Senior Advisor); November 29, 2016; https://blog.priceplow.com/wp-content/uploads/hi-tech-vs-fda-20161230-exhibit-35-deposition-of-cara-welch-20161129.pdf
  27. Hi-Tech Pharmaceuticals; Exhibit 16; Communications between Elaine Watson (NutraIngredients-USA), Lori Bestervelt (NSF), Amy Eichner (USADA), and Mahmoud ElSohly Regarding Embargoed Armstrong Study; May 22-23, 2012; https://blog.priceplow.com/wp-content/uploads/hi-tech-vs-fda-20161230-wenik-exhibit-16-embargoed-armstrong-study-shared-to-researchers-20120523.pdf
  28. John Wiley & Sons Ltd; “Strictly Embargoed Until 00.01 Hours (EDT), Wednesday, May 30th, 2012”; Physical Science Newsletter; May 22, 2012;  https://blog.priceplow.com/wp-content/uploads/armstrong-dmaa-study-original-press-release-20120522.docx
  29. Watson, Elaine; “USPLabs promises new data that ‘definitively’ proves presence of DMAA in geranium”; NutraIngredients-USA; July 16, 2012;  http://www.nutraingredients-usa.com/Research/USPLabs-promises-new-data-that-definitively-proves-presence-of-DMAA-in-geranium
  30. USPLabs; “Second Response Letter to Warning Letter No. 285519”; September 28, 2012; http://dmaaresearch.com/docs/FDA%20Warning%20Letter%20DMAA%20September%2028%202012%202nd%20Response.pdf (archived at https://blog.priceplow.com/wp-content/uploads/usplabs-fda-warning-letter-response-2-20120928.pdf)
  31. Thomas, Jennifer A; “Response Letter to USP Labs LLC Concerning DMAA”; Division of Enforcement, Office of Compliance, Center for Food Safety and Applied Nutrition, Food and Drug Administration; April 18, 2013;  https://www.fda.gov/aboutfda/centersoffices/officeoffoods/cfsan/cfsanfoiaelectronicreadingroom/ucm350199.htm
  32. PricePlow Blog; “$8 Million Worth of Jack3d and OxyELITE Pro… Down the Drain”; July 17, 2013;  https://blog.priceplow.com/jack3d-oxyelite-pro-destroyed
  33. Schultz, Hank; “FDA seizes another $2 million worth of DMAA products”; November 19, 2013; http://www.nutraingredients-usa.com/Regulation/FDA-seizes-another-2-million-worth-of-DMAA-products
  34. Morton, Lakisha N; US Food and Drug Administration; United States Department of Health and Human Services; “United States of America v Undetermined quantities of all articles of finished and in-process foods, raw ingredients (bulk powders, bulk capsules) listed below, with any lot number, size, or type container, whether labeled or unlabeled: et al.”; November 7, 2013; https://blog.priceplow.com/wp-content/uploads/hi-tech-vs-fda-20131107-fda-original-complaint.pdf
  35. Hi-Tech Pharmaceuticals; “Answer and Jury Demand on Behalf of Claimants Hi-Tech Pharmaceuticals, Inc. and Jared Wheat”; January 7, 2014;  https://blog.priceplow.com/wp-content/uploads/hi-tech-vs-fda-20140107-hi-tech-answer-to-original-complaint.pdf
  36. Mahmoud A. ElSohly, Waseem Gul, Candice Tolbert, Kareem M. ElSohly, Timothy P. Murphy, Bharathi Avula, Amar G. Chittiboyina, Mei Wang, Ikhlas A. Khan, Min Yang, Dean Guo, Wei-Dong Zhang, Juan Su; “Methylhexanamine is not detectable in Pelargonium or Geranium species and their essential oils: A multi-centre investigation”; Drug Testing and Analysis; Volume 7, Issue 7; July 2015; Pages 645–654; http://onlinelibrary.wiley.com/doi/10.1002/dta.1726/abstract
  37. Hi-Tech Pharmaceuticals; Exhibit 25; “Methylhexanamine is not detectable in Pelargonium or Geranium species and their essential oils: A multi-centre investigation”; August 29, 2014; https://blog.priceplow.com/wp-content/uploads/hi-tech-vs-fda-20161230-wenik-exhibit-25-multi-center-study.pdf
  38. Hi-Tech Pharmaceuticals; Exhibit 26; Email Exchange between Min Yang, Ikhlas Khan, and Mahmoud ElSohly; March 30, 2013 – April 4, 2013; https://blog.priceplow.com/wp-content/uploads/hi-tech-vs-fda-20161230-wenik-exhibit-26-email-exchange-dmaa-found-multi-center-geranium-study-20130404.pdf
  39. Hi-Tech Pharmaceuticals; Exhibit 5; Deposition of Daniel Fabricant (FDA); November 21, 2016; https://blog.priceplow.com/wp-content/uploads/hi-tech-vs-fda-20161230-wenik-exhibit-05-daniel-fabricant-deposition.pdf
  40. Easley, Jonathan; “Obama says his is ‘most transparent administration’ ever”; February 14, 2013; https://web.archive.org/web/20170707182633/http://thehill.com/blogs/blog-briefing-room/news/283335-obama-this-is-the-most-transparent-administration-in-history
  41. James Akrong Shawn Shirazi Vincent Scalisi Jason Peters; US Patent Application 20120225144A1: “Herbal Supplement Prepared From Geranium”; March 2, 2011; https://patents.google.com/patent/US20120225144A1/en
  42. Canada Intellectual Property Office; “Patent 2734231 Summary: HERBAL SUPPLEMENT PREPARED FROM GERANIUM”; December 18, 2012; http://www.ic.gc.ca/opic-cipo/cpd/eng/patent/2734231/summary.html
  43. Hi-Tech Pharmaceuticals; Exhibit 54; Deposition of Daniel Fabricant (FDA); November 18, 2016; https://blog.priceplow.com/wp-content/uploads/hi-tech-vs-fda-20161230-exhibit-54-daniel-kababick-deposition-20161118.pdf
  44. Hi-Tech Pharmaceuticals; Exhibit 52; Deposition of Dr. Paul Simone; November 7, 2016; https://blog.priceplow.com/wp-content/uploads/hi-tech-vs-fda-20161230-wenik-exhibit-52-deposition-of-dr-paul-simone-20161107.pdf
  45. Angelo Lisi, Nicole J. Hasick, Ray Kazlauskas, Catrin Goebel; “Studies of methylhexaneamine in supplements and geranium oil”; Drug Testing and Analysis; Volume 3, Issue 11-12; November-December 2011 ; Pages 873–876; http://onlinelibrary.wiley.com/doi/10.1002/dta.392/abstract (full-text available at https://www.docdroid.net and https://www.webcitation.org/6sFt9cZbM)
  46. ChemistryViews; “Sports Supplement Origin: Synthetic vs. Natural – Isotope Study Reveals Origin of Sports Suppliment”; May 30, 2012; Archived at archives of the original press release
  47. ChemistryViews; “Sports Supplement Origin: Synthetic vs. Natural – Isotope Study Reveals Origin of Sports Suppliment”; July 13, 2012; Archived at web.archive.org
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