Syntheses and Purification of Cannabinoid Derivatives
Location
Culp Center Ballroom
Start Date
4-25-2023 9:00 AM
End Date
4-25-2023 11:00 AM
Poster Number
117
Faculty Sponsor’s Department
Chemistry
Name of Project's Faculty Sponsor
Abbas Shilabin
Competition Type
Competitive
Type
Poster Presentation
Project's Category
Biochemistry
Abstract or Artist's Statement
Synthetic cannabinoids such as Δ8-Tetrahydrocannabinol (Δ8) are becoming increasingly popular. Δ8 was once studied for medicinal value and showed promise as an antiemetic. The typical synthesis of Δ8 includes a Cannabidiol (CBD) dissolved in a nonpolar solvent then reacted with a strong acid and washed in a basic solution to remove contaminants. We investigated the effects of varying the acid and solvent along with the washing method used in synthesizing Δ8 to produce novel synthetic cannabinoids and increase purity of Δ8. CBD was reacted with p-Toluenesulfonic acid monohydrate or Phosphotungstic acid dissolved in Toluene, Cyclohexene, or Cyclohexane. Samples were either washed with sodium bicarbonate or extracted from the non-polar layer when added to a biphasic solution of cyclohexane and either acetonitrile or ethanol. Samples were taken at 1-, 24-, 72-, 96-, 168-, and 288-hour increments. Samples were diluted with DCM and analyzed via GCMS. Notable cannabinoids synthesized include CBC, CBN, isomers of CBD, and unknown hydrated cannabinoids. Through comparative GCMS analysis cyclohexane was discovered to be the commercial solvent of choice. Residual cyclohexane (<4%) was identified in all similar samples and poses unknown toxicity. The biphasic extraction and wash produced samples with greater purity while also reducing byproduct contamination when compared to commercial samples. This work will be useful in identifying cannabinoid byproducts in the production of Δ8 from which future drugs may be developed. This work will also be key in highlighting hidden toxic compounds related to of unregulated synthetic cannabinoid production.
Syntheses and Purification of Cannabinoid Derivatives
Culp Center Ballroom
Synthetic cannabinoids such as Δ8-Tetrahydrocannabinol (Δ8) are becoming increasingly popular. Δ8 was once studied for medicinal value and showed promise as an antiemetic. The typical synthesis of Δ8 includes a Cannabidiol (CBD) dissolved in a nonpolar solvent then reacted with a strong acid and washed in a basic solution to remove contaminants. We investigated the effects of varying the acid and solvent along with the washing method used in synthesizing Δ8 to produce novel synthetic cannabinoids and increase purity of Δ8. CBD was reacted with p-Toluenesulfonic acid monohydrate or Phosphotungstic acid dissolved in Toluene, Cyclohexene, or Cyclohexane. Samples were either washed with sodium bicarbonate or extracted from the non-polar layer when added to a biphasic solution of cyclohexane and either acetonitrile or ethanol. Samples were taken at 1-, 24-, 72-, 96-, 168-, and 288-hour increments. Samples were diluted with DCM and analyzed via GCMS. Notable cannabinoids synthesized include CBC, CBN, isomers of CBD, and unknown hydrated cannabinoids. Through comparative GCMS analysis cyclohexane was discovered to be the commercial solvent of choice. Residual cyclohexane (<4%) was identified in all similar samples and poses unknown toxicity. The biphasic extraction and wash produced samples with greater purity while also reducing byproduct contamination when compared to commercial samples. This work will be useful in identifying cannabinoid byproducts in the production of Δ8 from which future drugs may be developed. This work will also be key in highlighting hidden toxic compounds related to of unregulated synthetic cannabinoid production.