Cannabidiol revisited

Abstract

The crystal structure of cannabidiol, C21H30O2, {systematic name: 2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-enyl]-5-pentylbenzene-1,3-diol}, was determined earlier by Joneset al.[(1977).Acta Cryst.B33, 3211–3214] and Ottersen & Rosenqvist [(1977).Acta Chem. Scand.B31, 749–755]. In both investigations, the absolute configuration is given asR,R, referring to Mechoulamet al.[(1967.J. Am. Chem. Soc.89, 4552–4554]. In the latter, the absolute configuration was identified by chemical means. Using the advantages of modern single-crystal X-ray diffractometers such as area detectors and high-intensity radiation sources, a high-quality structure determination including the absolute configuration was possible and is shown in this work. Furthermore, the rather uncommon CuKβ wavelength radiation was applied for the structure determination, which confirmed the absolute structure to beR,R.

Towards Better Delivery of Cannabidiol (CBD)

“…As stated by the FDA’s guidance document “polymorphism can affect the quality, safety, and efficacy of the drug product”; so controlling polymorphism from the drug substance can provide an easier development with regards to regulatory approval [ 50 ]. CBD has been shown to be present as two or more inherent crystalline forms which have potential effects on drug absorption and bioavailability due to different physicochemical properties [ 6 ]. To date, no studies have assessed how different crystalline forms may impact the pharmacokinetic profile of CBD, which may have implications for CBD being developed as solid-state forms.…”

“…In order to be successfully utilised as a medicine, it is paramount to identify and overcome the inherent challenges that face CBD’s effective delivery, particularly through the oral route, which is the most preferred route for drug delivery by patients and drug developers. Some of the most significant issues with oral CBD include poor bioavailability, variable pharmacokinetics profiles, and possible polymorphisms [ 6 ], which may have unintended consequences of less predictable efficacy, increased side effects and drug–drug interactions with higher doses. This review will outline some of the current issues with CBD pharmaceutics, the novel CBD formulations under development and under clinical investigation, and the strategies to improve CBD delivery and efficacy.…”

Untitled

“…The unique Cu Kf3 wavelength radiation determined that the absolute structure was R,R-the same as the Cannabidiol structure represented by Mechoulam. We found an identical crystal structure to CBD from cannabis sativa (Mayr, Grassl, Korber, Christoffel & Bodensteiner, 2017).…”

Nanotechnology to deliver cannabinoids in dermatology

“…In addition, multiple inherent crystalline structures for many cannabinoid compounds further complicate formulation as these polymorphisms can lead to changes in molecular conformations that can also influence solubility and degradation. 8,35 Drug delivery vehicles that can adequately maintain the intended drug dose in solute form while ensuring the physical stability of the preparation are crucial for the dermatologic utility of cannabinoids.…”