Decarboxylation Study of Acidic Cannabinoids: A Novel Approach Using Ultra-High-Performance Supercritical Fluid Chromatography/Photodiode Array-Mass Spectrometry

• Published in: Cannabis and cannabinoid research 2016-12, Vol.1 (1), p.262-271
• Main Authors: Wang, Mei, Wang, Yan-Hong, Avula, Bharathi, Radwan, Mohamed M, Wanas, Amira S, van Antwerp, John, Parcher, Jon F, ElSohly, Mahmoud A, Khan, Ikhlas A
• Format: Article
• Language: English
• Subjects: Acids; Chromatography; Kinetics; Marijuana; Mass spectrometry; Medical research; Original Research; Oxidation; Scientific imaging; Studies
• ISSN: 2378-8763; 2578-5125; 2378-8763
• DOI: 10.1089/can.2016.0020

Decarboxylation is an important step for efficient production of the major active components in cannabis, for example, Δ -tetrahydrocannabinol (Δ -THC), cannabidiol (CBD), and cannabigerol (CBG). These cannabinoids do not occur in significant concentrations in cannabis but can be formed by decarboxylation of their corresponding acids, the predominant cannabinoids in the plant. Study of the kinetics of decarboxylation is of importance for phytocannabinoid isolation and dosage formulation for medical use. Efficient analytical methods are essential for simultaneous detection of both neutral and acidic cannabinoids. extracts were used for the studies. Decarboxylation conditions were examined at 80°C, 95°C, 110°C, 130°C, and 145°C for different times up to 60 min in a vacuum oven. An ultra-high performance supercritical fluid chromatography/photodiode array-mass spectrometry (UHPSFC/PDA-MS) method was used for the analysis of acidic and neutral cannabinoids before and after decarboxylation. Decarboxylation at different temperatures displayed an exponential relationship between concentration and time indicating a first-order or -first-order reaction. The rate constants for Δ -tetrahydrocannabinolic acid-A (THCA-A) were twice those of the cannabidiolic acid (CBDA) and cannabigerolic acid (CBGA). Decarboxylation of THCA-A was forthright with no side reactions or by-products. Decarboxylation of CBDA and CBGA was not as straightforward due to the unexplained loss of reactants or products. The reported UHPSFC/PDA-MS method provided consistent and sensitive analysis of phytocannabinoids and their decarboxylation products and degradants. The rate of change of acidic cannabinoid concentrations over time allowed for determination of rate constants. Variations of rate constants with temperature yielded values for reaction energy.