A method of increasing the cannabinoid levels in a genetically modified Cannabis sativa plant includes genetically modifying the plant to induce the overexpression of the gene that controls the expression of tetrahydrocannabinolic acid (THCA) synthase and/or cannabidiolic acid (CBDA) synthase. The overexpression of THCA synthase and CBDA synthase catalyzes an increased synthesis of cannabigerolic acid to tetrahydrocannabinolic acid and cannabidiolic acid, as well as the cannabinoids (3aR)-2,4,4-trimethyl-7-pentyl-3,3a,4,9b-tetrahydrocyclopenta[c]chromen-9-ol and 2-((1R,5R)-3-methyl-5-(prop-1-en-2-yl)cyclopent-2-en-1-yl)-5-pentylbenzene-1,3-diol. Pharmaceutical compositions comprising the modified cannabinoids produced by the transgenic Cannabis sativa plant or prepared synthetically are used to treat various diseases and conditions.

The present disclosure provides processes for the preparation of a compound of formula: ##STR00001##
which is useful as an antiviral agent. The disclosure also provides compounds that are synthetic intermediates.

The present disclosure provides processes for the preparation of a compound of formula: ##STR00001##
which is useful as an antiviral agent. The disclosure also provides compounds that are synthetic intermediates.

The present invention relates to novel cannabinoids 1 and 2, synthesized from simple starting materials using a cascade sequence of allylic rearrangement, aromatization and, for tetracyclic cannabinoids, further highly stereoselective and regioselective cyclization. These synthesized cannabinoids can more easily be obtained at high purity levels than cannabinoids isolated or synthesized via known methods. The cannabinoids 2 are obtained containing very low levels of isomeric cannabinoids such as the undesirable Δ8-tetrahydrocannabinol. The analogues with variation in aromatic ring substituents, whilst easily synthesized with the new methodology, would be much more difficult to make from any of the components of cannabis oil. Novel compounds of the formulas 3, 4, 5 and 6, as intermediates for the synthesis of the cannabinoids of the formulas 1 and 2 are also disclosed.

The present invention relates to novel cannabinoids 1 and 2, synthesized from simple starting materials using a cascade sequence of allylic rearrangement, aromatization and, for tetracyclic cannabinoids, further highly stereoselective and regioselective cyclization. These synthesized cannabinoids can more easily be obtained at high purity levels than cannabinoids isolated or synthesized via known methods. The cannabinoids 2 are obtained containing very low levels of isomeric cannabinoids such as the undesirable Δ8-tetrahydrocannabinol. The analogues with variation in aromatic ring substituents, whilst easily synthesized with the new methodology, would be much more difficult to make from any of the components of cannabis oil. Novel compounds of the formulas 3, 4, 5 and 6, as intermediates for the synthesis of the cannabinoids of the formulas 1 and 2 are also disclosed.

A cannabis processing system comprises a grinding apparatus and a cell disruption apparatus. The grinding apparatus is configured to grind wet cannabis cuttings to from a ground, wet cannabis material comprising wet cannabis particles having an average particle size within a range of from about 1 mm to about 3 mm. The cell disruption apparatus is downstream of the grinding apparatus and is configured to disrupt cell walls of plant cells of the wet cannabis particles through one or more of flash freezing, a cellulose solvent, applied negative pressure, and vacuum distillation to facilitate removal of one or more cannabinoids within the plant cells of the wet cannabis particles. Methods of processing cannabis are also described.

A cannabis processing system comprises a grinding apparatus and a cell disruption apparatus. The grinding apparatus is configured to grind wet cannabis cuttings to from a ground, wet cannabis material comprising wet cannabis particles having an average particle size within a range of from about 1 mm to about 3 mm. The cell disruption apparatus is downstream of the grinding apparatus and is configured to disrupt cell walls of plant cells of the wet cannabis particles through one or more of flash freezing, a cellulose solvent, applied negative pressure, and vacuum distillation to facilitate removal of one or more cannabinoids within the plant cells of the wet cannabis particles. Methods of processing cannabis are also described.

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.

Provided herein are methods for converting CBD to a product mixture comprising Δ.sup.8-THC, Δ.sup.9-THC, or a combination thereof. The methods provided herein may comprise one or more of (1) a contacting step wherein a starting material comprising CBD, a catalyst comprising a zeolite, and optionally a solvent are added to a reaction vessel, thereby forming a reaction mixture; (2) a conversion step wherein at least a portion of the CBD is converted to THC, thereby forming a product mixture; and (3) optionally, a separation step wherein at least a portion of the catalyst is removed from the product mixture. Advantageously, the methods do not require the use of catalysts or other reagents that are hazardous to human health.