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Published on: December 4, 2016
Structure elucidation of the tetrahydrocannabinol complex with randomly methylated beta-cyclodextrin
1Department of Pharmacognosy, Leiden University, Institute of Biology, Leiden, The Netherlands. ahazekamp@rocketmail.com
Summary
Randomly methylated beta-cyclodextrin (RAMEB) significantly enhances tetrahydrocannabinol (THC) solubility, overcoming a major hurdle for developing new THC formulations. This cyclodextrin complexation offers a promising avenue for water-based THC delivery systems.
Area of Science:
- Pharmaceutical Sciences
- Drug Delivery
- Medicinal Chemistry
Background:
- Tetrahydrocannabinol (THC) exhibits poor aqueous solubility, limiting its therapeutic applications.
- Developing effective administration routes for cannabinoids like THC is crucial for pharmaceutical advancement.
Purpose of the Study:
- To investigate the potential of various cyclodextrins (CDs) in enhancing the aqueous solubility of tetrahydrocannabinol (THC).
- To characterize the complex formed between THC and the most effective cyclodextrin, RAMEB.
Main Methods:
- Phase-solubility analysis was employed to assess THC solubility with different cyclodextrins.
- (1)H NMR, NOESY, and UV-Vis spectroscopy were used to study the THC/RAMEB complex.
- Complex stability was evaluated under standard laboratory conditions for up to eight weeks.
Main Results:
- Randomly methylated beta-cyclodextrin (RAMEB) significantly increased THC aqueous solubility by four orders of magnitude, reaching approximately 14 mg/ml.
- Complexation studies revealed a 2:1 binding ratio of THC to RAMEB, with evidence of non-inclusion interactions for the second THC molecule.
- The THC/RAMEB complex demonstrated stability over an 8-week period.
Conclusions:
- RAMEB is highly effective in solubilizing THC, presenting a viable strategy for overcoming solubility challenges.
- The characterized THC/RAMEB complex provides insights into its structure and binding interactions.
- Complexation with RAMEB shows significant promise for the development of novel, water-based THC formulations.
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