Provided herein are cannabinoid analogs, including halogenated cannabinoid analogs, hydroxylated cannabinoid analogs, deuterated cannabinoid analogs, and tritiated cannabinoid analogs. The cannabinoid analogs can be prepared by partial or total expression in modified host cells, such as recombinantly modified yeast cells, optionally in combination with chemical synthetic steps.

Disclosed are methods for separating, recovering, and purifying tetrahydrocannabinolic acid (THCA) salts from an organic solvent solution comprising a mixture of cannabinoids. The methods comprise solubilizing the mixture of cannabinoids in a selected C5-C7 hydrocarbon solvent, adding thereto a selected amine to thereby precipitate a THCA-amine salt therefrom, dissolving the recovered THCA-amine salt in a selected solvent and then adding thereto a selected antisolvent to thereby recrystallize a purified THCA-amine salt therefrom. The recrystallized THCA-amine salt may be decarboxylated to form a mixture of Δ9-tetrahydrocannabinol (Δ9-THC) and amine. The Δ9-THC amine mixture may be acidified to separate the amine from Δ9-THC. The recovered Δ9-THC may be concentrated to produce a highly purified Δ9-THC. Also disclosed are THCA-amine salts produced with amines selected from groups of diamines, amino alcohols, and tertiary amines.

Disclosed are methods for separating, recovering, and purifying tetrahydrocannabinolic acid (THCA) salts from an organic solvent solution comprising a mixture of cannabinoids. The methods comprise solubilizing the mixture of cannabinoids in a selected C5-C7 hydrocarbon solvent, adding thereto a selected amine to thereby precipitate a THCA-amine salt therefrom, dissolving the recovered THCA-amine salt in a selected solvent and then adding thereto a selected antisolvent to thereby recrystallize a purified THCA-amine salt therefrom. The recrystallized THCA-amine salt may be decarboxylated to form a mixture of Δ9-tetrahydrocannabinol (Δ9-THC) and amine. The Δ9-THC amine mixture may be acidified to separate the amine from Δ9-THC. The recovered Δ9-THC may be concentrated to produce a highly purified Δ9-THC. Also disclosed are THCA-amine salts produced with amines selected from groups of diamines, amino alcohols, and tertiary amines.

Disclosed is a method for preparing cannabidiol and analogues thereof; the method is implemented by means of reacting a resorcinol derivative with menthyl-2,8-dien-1-ol or a derivative thereof. The method of the present invention has advantages of such as high chemical reaction selectivity and simple operation.

Disclosed is a method for preparing cannabidiol and analogues thereof; the method is implemented by means of reacting a resorcinol derivative with menthyl-2,8-dien-1-ol or a derivative thereof. The method of the present invention has advantages of such as high chemical reaction selectivity and simple operation.

A method of removing THC and/or THCA from a mixture, the mixture including THC and/or THCA and at least one cannabinoid is provided. The method comprises passing a first feedstock stream through a first chromatographic resin arranged in a simulated moving bed (SMB) chromatography configuration to provide a primary raffinate stream, preparing a second feedstock stream, the second feedstock stream comprising the primary raffinate stream or a concentrated primary raffinate stream, and passing the second feedstock stream through a second chromatographic resin to provide an eluate stream, the eluate stream having less than 0.3 wt % THC on a solvent free basis. The cannabinoid products can be used in various pharmaceutical and nutraceutical applications.

A method of removing THC and/or THCA from a mixture, the mixture including THC and/or THCA and at least one cannabinoid is provided. The method comprises passing a first feedstock stream through a first chromatographic resin arranged in a simulated moving bed (SMB) chromatography configuration to provide a primary raffinate stream, preparing a second feedstock stream, the second feedstock stream comprising the primary raffinate stream or a concentrated primary raffinate stream, and passing the second feedstock stream through a second chromatographic resin to provide an eluate stream, the eluate stream having less than 0.3 wt % THC on a solvent free basis. The cannabinoid products can be used in various pharmaceutical and nutraceutical applications.

A method for chemical separation of cannabinoids includes: (i) providing a starting organic solvent solution that contains a mixture of cannabinoid acids, (ii) using an aqueous basic solution to remove a portion of the cannabinoid acids from the mixture of cannabinoid acids in the starting organic solvent solution by converting the portion of the cannabinoid acids to cannabinoid carboxylate salts that solubilize in the an aqueous basic solution, (iii) separating the aqueous basic solution in (ii) from the starting organic solvent, (iv) combining the aqueous solution from (iii) with new organic solvent to produce a combined solution, (v) acidifying the combined solution to extract the cannabinoid acids from the aqueous solution to the organic solvent, (vi) separating the organic solvent of (v) from the aqueous solution, and (vii) evaporating the organic solvent of (vi) to leave product cannabinoid acids.

A method for chemical separation of cannabinoids includes: (i) providing a starting organic solvent solution that contains a mixture of cannabinoid acids, (ii) using an aqueous basic solution to remove a portion of the cannabinoid acids from the mixture of cannabinoid acids in the starting organic solvent solution by converting the portion of the cannabinoid acids to cannabinoid carboxylate salts that solubilize in the an aqueous basic solution, (iii) separating the aqueous basic solution in (ii) from the starting organic solvent, (iv) combining the aqueous solution from (iii) with new organic solvent to produce a combined solution, (v) acidifying the combined solution to extract the cannabinoid acids from the aqueous solution to the organic solvent, (vi) separating the organic solvent of (v) from the aqueous solution, and (vii) evaporating the organic solvent of (vi) to leave product cannabinoid acids.

Disclosed are compounds that can modulate DDAH and the amount of asymmetric dimethylarginine (ADMA) in a subject. Also provided are pharmaceutical compositions comprising these compounds, as well as methods of using these compositions to treat and/or prevent diseases associated with elevated or low levels of DDAH and ADMA.