∆8-THC, THC-O Acetates and CBD-di-O Acetate: Emerging Synthetic Cannabinoids Found in Commercially Sold Plant Material and Gummy Edibles

Abstract

Presented is the analysis of four cannabinoid-based products. These products were part of a case involving visual and auditory hallucinations that precipitated the commission of a felony and subsequent arrest. The products were labeled to contain ∆8-tetrahydrocannabinol (∆8-THC) or THC acetate (THC-O-A). Primary reference materials were not available for ∆8-THC-O-A, ∆10-THC-O-A, cannabidiol di-acetate (CBD-di-O-A) or respective deuterated internal standards. THC-O-A and CBD-di-O-A standards were prepared by derivatizing ∆8-THC, ∆9-THC, ∆10-THC, CBD, ∆9-THC-d3 and CBD-d3 using acetic anhydride. The cannabinoid-based products were determined to contain ∆8-THC, ∆8-THC-O-A, ∆9-THC-O-A and CBD-di-O-A and/or other phytocannabinoids using three different analytical techniques. Direct analysis in real-time-time-of-flight mass spectrometry was used for identifying exact masses. A gas chromatograph-mass spectrometer was used for the identification of compounds and to quantitate THC-O-As in the products. A liquid chromatograph-tandem mass spectrometer was used to identify and quantitate phytocannabinoids and CBD-di-O-A in the products. To the authors' knowledge, this is the first case report involving the identification of THC-O-As and CBD-di-O-A in commercially available products. Minimal clinical/pharmacological data is available for these emerging synthetic cannabinoids/novel psychoactive substances.

Figure 1.

Product characterization results for Ouachita Farms “Hawaiian Haze CBD flower”. Top: DART–MS spectrum. Bottom: Total ion chromatogram. Bottom insert: quantitative results of targeted analyses.

Figure 2.

Product characterization results for Moon Men “Alien Cookies Delta 8 Flower”. Top: DART–MS spectrum. Bottom: GC--MS Total ion chromatogram. Bottom insert: quantitative results of targeted analyses.

Figure 3.

Product characterization results for Elysian “Delta 8 Flower”. Top: DART–MS spectrum. Bottom: Total ion chromatogram. Bottom insert: quantitative results of targeted analyses.

Figure 4.

Product characterization results for Palm Treez Gummy Squares. Top: DART–MS spectrum. Bottom: GC--MS Total ion chromatogram. Bottom insert: quantitative results of targeted analyses.

Figure 5.

Separation of cannabinoids and cannabinoid acetate derivatives by gas chromatography–mass spectrometry, with acetate structures and mass spectrums.