Cannabis Analysis II: Detection of Cannabinoid Acids that Inhibit COVID-19 Infection in Consumer Products

The cannabis plant (Cannabis Sativa L., aka hemp) produces a variety of compounds covering numerous chemical classes such as cannabinoids, terpenes, and terpenoids. The cannabinoid subclass which produces psychoactive and other pharmacological effects includes chemically neutral and acidic compounds. Cannabinoid acids were recently proven to be effective at binding to the spike protein of the COVID-19 virus and thus inhibited cell entry, replication, and infection. Analysis of these compounds can be performed by numerous techniques including Gas Chromatography-Electron Impact-Mass Spectrometry (GC-EI-MS). We developed a targeted methodology to analyze four of the known acids commonly found in consumer products by GC-EI-MS. Since the cannabinoid acids are prone to decarboxylate at elevated temperatures and revert to their neutral counterparts (ex. CBDA to CBD, THCA to THC), they are found formulated mainly into non-smokable consumer products. The elevated temperatures used in GC-EI-MS analysis necessitated the addition of a protective group to active –OH groups via derivatization. This methodology proved to be effective at overcoming decarboxylation and allowed the acids to survive the analysis

Optimization of GC Assay for 1,3-dimethylamylamine

The subject compound, 1,3-dimethylamylamine (DMAA), is a “natural” stimulant found in nutritional supplements, weight loss, and athletic performance-enhancing products. This amphetamine-like compound is linked to cardiovascular problems such as shortness of breath, arrhythmias, chest tightness, heart attacks, and multiple deaths [ref 1]. DMAA was banned in 2010 by the International Association of Athletics and the International Olympic Committee which both abide by the policies set forth by the World Anti-Doping Agency [ref 2]. Our laboratory recently developed a quantitative method to determine the presence and amount of DMAA in commercial products by GC-FID and GC-MS. The purpose of this project was to optimize the sensitivity of the existing analytical method to quantitate DMAA via derivatization using alkanoic anhydrides of varying molecular weight

Cannabis Analysis III: Improved Separation of Terpenes and Terpenoids

The cannabis plant (Cannabis Sativa L.) produces a variety of compounds covering numerous chemical classes such as cannabinoids, terpenes, and terpenoids. Terpenes and terpenoids are responsible for the aroma characteristics and a variety of purported medical benefits. Terpenes are oligomers of isoprene units, whereas terpenoids are oxidized forms of terpenes. Analysis of these compounds is typically performed by Gas Chromatography (GC) via liquid injection or gas injection (Headspace). Due to the wide boiling point range of these compounds, operational cannabis laboratories most often perform the analysis using liquid injection. However, separation of the numerous and wide variety of compounds in the relatively short period of time needed for high throughput is challenging. We have determined that separation (selectivity) of terpenes and terpenoids commonly found in consumer products was improved by modifying GC column stationary phase chemistry. This improvement in selectivity will ultimately improve identification and quantitation of these compounds

Robustness of VSL Values from Contingent Valuation Surveys

This paper examines factors that may influence the estimates of the Value of a Statistical Life obtained from contingent valuation surveys that elicit the willingness to pay (WTP) for mortality risk reductions. We examine the importance of distributional assumptions, the choice of the welfare statistics of interest, the procedure for computing them, outliers, undesirable response effects, and internal validity of the WTP responses. We illustrate the importance of these factors using dichotomous-choice and open-ended WTP data from four recent contingent valuation surveys

GC-MS Analysis of Pyrogallol and Purpurogallin

Pyrogallol is a polyphenol formed from the decarboxylation of gallic acid found in tannins. Drinks like tea and coffee contain high levels of tannins that are responsible for staining of teeth and other surfaces. Purpurogallin is an oxidation product of pyrogallol. In this work, which was a collaboration with Professor Conrad Naleway’s research group in the Department of Chemistry and Biochemistry, we developed a method to derivatize pyrogallol and purpurogallin and analyze the products by GCMS. The analytical challenge was to derivatize a crowded arrangement of -OH groups on neighboring carbons and get all to accept a derivatizing group, quantitatively

Cannabis Analysis I: What’s in a Cannabis Gummy Bear?

A better question may be “What’s on a Cannabis Gummy Bear?” The widespread legalization of cannabis (Cannabis Sativa L.) in the US at the state level has spawned the production of a wide variety of consumer products containing chemical constituents derived from the cannabis plant. These compounds are typically extracted from the plant by various means and formulated into both edible and non-edible products. The main classes of compounds found in consumer products are cannabinoids, terpenes, and terpenoids. Over time, public acceptance has grown for the use of gelatin-based products (i.e., gummies) as oral delivery vehicles for vitamins, supplements, and drugs. Cannabis gummies are no exception. Cannabis gummies are formulated in two basic ways: infused with cannabis extracts during the compounding process or coated with the extracts in a final step after the gummy has formed. Chemical analysis of any finished product requires analytical laboratories to break down the product matrix to release the compounds which may be bound strongly to matrix components within the product. Since gummies are formulated with water, it is common practice to re-dissolve the gummy in an excess of water and then analyze the aqueous solution directly or extract the solution with a suitable organic solvent. The focus of this work was to determine an efficient means of extracting cannabidiol (CBD) in a variety of gummy products followed by analyses using Gas Chromatography - Electron Impact - Mass Spectrometry (GC-EI-MS). Ultimately, we determined that CBD coated gummies could be extracted directly with organic solvents, without the need for initial dissolution in water