Deuterated Cannabinoid Derivatives for Metabolic Stability
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Solution Overview
Problem
Cannabinoids obtained from natural plant sources are costly and may contain impurities, and existing methods do not effectively address metabolic issues of cannabinoids.
Innovation Solution
Development of 8,9-dihydrocannabinoid, deuterated, and tritiated derivatives, along with pharmaceutical compositions and synthesis methods using homogeneous and heterogeneous catalysts to improve bioavailability and metabolic stability.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If cannabinoids are obtained by isolation from natural plant sources, then the compounds can be obtained, but the cost is high and impurities are present
Solution Approach 1:
The patent extracts only the necessary cannabinoid structures from complex plant sources and reproduces them through synthetic chemistry. By taking out the active pharmacophore and synthesizing it de novo, the method eliminates impurities inherent in plant extraction while reducing costs through efficient synthetic routes.
Solution Approach 2:
The patent creates synthetic copies of natural cannabinoids through chemical synthesis. These copied molecules have identical or improved pharmacological properties but are free from plant-derived impurities and can be produced more cost-effectively through scalable synthetic methods.
2Reliability
If deuterated cannabinoids are used, then bioavailability is improved and metabolism is slowed, but the complexity of preparation increases
Solution Approach 1:
The patent changes the isotopic parameter of hydrogen atoms to deuterium at specific positions in the cannabinoid structure. This parameter change slows metabolic C-H bond cleavage, improving metabolic stability and bioavailability while maintaining the molecule's overall structure and pharmacological activity.
3Stability of the object's composition
If 8,9-dihydrocannabinoid derivatives are synthesized, then metabolic stability is improved, but the synthesis process becomes more complex
Solution Approach 1:
The patent changes the saturation parameter at the 8,9-position of the cannabinoid ring system, converting the double bond to a single bond. This structural parameter change improves metabolic stability by eliminating a site susceptible to oxidative metabolism, while the synthesis complexity is managed through efficient hydrogenation steps.
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
Enhances bioavailability and metabolic stability of cannabinoids, potentially improving therapeutic efficacy and reducing impurities.
Implementation Method 1
synthesis methods using homogeneous and heterogeneous catalysts
Implementation Method 2
The preparation and use of deuterated cannabinoids can improve bioavailability and slow metabolism in relation to counterpart non-deuterated cannabinoids
Data Source
AI summary
This disclosure provides 8,9-dihydrocannabinoid derivatives, deuterated cannabinoid derivatives, and tritiated cannabinoid derivatives. The disclosure also provides compositions, methods of use, and processes of preparation of the foregoing derivatives.