Nonpsychotropic Synthetic Cannabinoids

Abstract

Unlike natural cannabinoids which belong to the 6aR - trans series, the synthetic dexanabinol (HU-211), a 6aS-trans enantiomer, does not have affinity toward cannabinoid receptors and is devoid of cannabimimetic activity. On the other hand, dexanabinol demonstrated significant neuroprotective properties which prompted its development as a therapeutic agent. We now present the extension of a series of 6aS-trans cannabinoids with novel derivatives, including water soluble derivatives and congeners of dexanabinol.

Ionic Liquids as Fragrance Precursors: Smart Delivery Systems for Volatile Compounds

“…As can be seen in Figure , [Cho]­[Ger-Succ] was observed to be more stable under acidic conditions (pH 3), while considerably faster hydrolysis was observed under basic conditions (pH 9) with complete cleavage in 250 min. This behavior has been previously reported for ester prodrugs, where base-catalyzed hydrolysis was observed for cannabinoid ester prodrugs, while stability increased at acidic pH. , …”

“…This behavior has been previously reported for ester prodrugs, where base-catalyzed hydrolysis was observed for cannabinoid ester prodrugs, while stability increased at acidic pH. 45,46 The synthetic strategy of making a hemisuccinate fragrance used for the synthesis of [Cho][Ger-Succ] also allows one to include a second active cation to form a dual functional IL. To test this hypothesis, Ger-hemisuccinate (Scheme 2) was reacted with the permanent cationic tetrabutylphosphonim and benzethonium hydroxides ( This profragrance approach demonstrates that one can choose a complementary cation that allows one to modify the physical properties of the profragrance liquid without modification of the active ingredient.…”

Chemical stabilization of a Δ9-tetrahydrocannabinol prodrug in polymeric matrix systems produced by a hot-melt method: Role of microenvironment pH

“…26,27 The ester prodrugs of a synthetic cannabinoid, dexanabinol, hydrolyzed rapidly at basic pH (9.0), while stability increased considerably at an acidic pH (1.2). 6 The base-catalyzed hydrolysis was much faster than that of the acid-catalyzed reaction.…”

“…Thus, various cannabinoids with nonpsychotropic activity were synthesized, such as dexanabinol and its derivatives (including prodrugs) with increased solubility in water. 6 To overcome the pharmacokinetic limitations associated with THC, ElSohly et al 7,8 explored the utility of various ester prodrugs in suppository formulations as alternatives for effecting the systemic delivery of THC. Studies using the hemisuccinate ester (THC-HS) in a lipophilic base in dogs exhibited ~64% bioavailability.…”