Synthesis of Fluorinated Cannabinoids

Enhancing the Bioavailability of Cannabinoids with Therapeutic Benefits

At a Glance

Researchers at Colorado State University have developed a method to synthesize fluorinated cannabinoids using cannabinol (CBN). Eight novel fluorinated compounds have been synthesized, and the methods optimized.

Background

Cannabis compounds such as cannabinoids offer a wide range of therapeutic benefits. For instance, cannabinoids have applications in pain, multiple sclerosis, nausea, posttraumatic stress disorder, cancer, epilepsy, cachexia, glaucoma, HIV/AIDS, and degenerative neurological illnesses. However, most cannabinoids, including cannabidiol (CBD), have a complicated pharmacokinetic profile due to their high lipophilicity, poor solubility, and first-pass metabolism. All these characteristics contribute to a low bioavailability, the rate at which a chemical is absorbed by the bloodstream.

Tetrahydrocannabinol (THC) and CBD have been extensively studied as they occur in greater amounts in the cannabis plant, whereas cannabinol (CBN) must be converted from CBD or THC. However, there are distinct advantages of CBN compared to CBD, including enhanced bioavailability. Therefore, there exists a need to develop cannabinoids, particularly CBN derivatives, that provide benefits such as enhanced bioavailability.

Overview

Accordingly, CSU Researchers have developed the synthetic methods of fluorinating cannabinoids with the aim of providing cannabinoid compositions with enhanced bioavailability. Four novel fluorinated cannabinoids have been synthesized, isolated, and characterized. Characterization data has not yet been published but can be provided upon request. Fluorinated cannabinoids are of interest for medical applications in treating a variety of diseases. The research team plans to obtain bioavailability and toxicity data soon.

Fluorination of compounds can provide enhanced pharmacokinetic and physicochemical characteristics, and therefore, can in turn increase the bioavailability of the resulting compound. Furthermore, this innovative method of making the novel fluorinated cannabinoids is less energy and time-consuming compared to traditional pathways. Thus, a lower energy input and time may be advantageous in providing higher yields and novel cannabinoid compositions.

Benefits

  • Uses less energy than traditional methods of fluorination.
  • Quicker than traditional methods of fluorination.
  • High Yielding synthesis and isolation methods.

Applications

  • Cancer treatment.
  • Pain and nausea management.
  • Epilepsy, cachexia, glaucoma, HIV/AIDS, and degenerative neurological illnesses therapies.
  • Use in combination with other effective drugs.
Last Updated: May 2024
Opportunity

Available for Exclusive Licensing
TRL: 3

IP Status

US Provisional Patent

Inventors

Ken Olejar Jr.
Urvashi
John Hatfield
Melvin Druelinger

Reference Number
2023-098 and 2024-065
Licensing Manager

Jessy McGowan
Jessy.McGowan@colostate.edu
970-491-7100