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Solid delta9-tetrahydrocannabinol (delta9-thc) compositions

a technology of delta9 and tetrahydrocannabinol, which is applied in the direction of lyophilised delivery, medical preparations, granular delivery, etc., can solve the problems of inability to store the pharmaceutical formulation in the refrigerator, the inability to manufacture, and the inability to adapt to the use of sup>9/sup>-th

Inactive Publication Date: 2022-01-20
CANNA CHEMISTRIES LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The invention is about creating a solid Δ9-THC composition that can be used for therapeutic or nutritional purposes. This composition is made by combining Δ9-THC with a powder former like adenine, aspartame, caffeine, lactose, or valine. The powder former helps to create a flowable powder that can be easily used for various applications like pharmaceutical or nutraceutical use. The solid Δ9-THC composition can also be used in food and beverage products. The technical effect of this invention is that it provides a convenient and flexible way to utilize Δ9-THC for therapeutic or nutritional purposes.

Problems solved by technology

The disadvantage is that in this formulation Δ9-THC is not stable.
The low stability of a compound and the need to store the pharmaceutical formulation in the refrigerator is a serious drawback for a pharmaceutical product.
Accordingly, Δ9-THC is extremely difficult to formulate and is not readily adapted for incorporation into standard dosage forms that are typically available for other, solid pharmaceutical compounds.

Method used

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  • Solid delta9-tetrahydrocannabinol (delta9-thc) compositions
  • Solid delta9-tetrahydrocannabinol (delta9-thc) compositions
  • Solid delta9-tetrahydrocannabinol (delta9-thc) compositions

Examples

Experimental program
Comparison scheme
Effect test

example 1

up>9-THC Compositions by Freeze-Drying (Lyophilization)

[0095]A commercially available Δ9-THC-acetonitrile solution (Cayman Chemical), approximately 50 mg Δ9-THC per mL, was used. The actual concentration was determined gravimetrically by taring a vial and recording its weight, adding 1 mL of solution, evaporating the solution, vacuum drying the sample at room temperature for 12 hours and reweighing the vial. The actual concentration was determined to be 51 mg / mL. Into 1 dram vials, 300 μl of the Δ9-THC acetonitrile solution was dispensed and allowed to evaporate at room temperature resulting in each vial containing ca. 15.3 mg of Δ9-THC.

[0096]Δ9-THC (ca. 15.3 mg) was dissolved in dioxane (3 mL solvent used) and transferred into a 25 mL round bottom flask. The powder former (amount based on 1:1, 1:2 or 1:4 molar Δ9-THC:powder former ratio) was dissolved in H2O (2 mL) and, if needed, dioxane (2 mL) was added to form a solution. The powder former solution was added to the Δ9-THC soluti...

example 2

up>9-THC Compositions by Evaporation

[0100]Δ9-THC (ca. 15.3 mg, prepared as in Example 1) was dissolved in methanol (MeOH) (1 mL). A powder former (amount based on a 1:1 Δ9-THC:powder former molar ratio) was added to the solution. If needed, additional MeOH (1-3 mL) was added until solids dissolved completely. The vial was left uncapped for fast evaporation (FE) at ambient temperature. The powder formers used were aspartame, caffeine, histidine, lactose and L-pipecolic acid. The Δ9-THC / histidine mixture resulted in a gel after evaporation. The other Δ9-THC / powder former mixtures were flowable powders and remained flowable powders when left at ambient temperature. The XRPD patterns were obtained for the Δ9-THC / aspartame powder (FIG. 21), Δ9-THC / caffeine powder (FIG. 22), and Δ9-THC / L-pipecolic acid powder (FIG. 23). Each XRPD pattern showed the presence of some crystalline powder former and an amorphous halo.

example 3

up>9-THC Compositions by Physical Mixing

[0101]Δ9-THC (ca. 15.3 mg, prepared as in Example 1) and a powder former (amount based on 1:1 Δ9-THC:powder former molar ratio) were placed in a 1 dram vial. The solids were mixed with a glass stir rod and metal spatula. The powder formers used were aspartame, caffeine, histidine, lactose and L-pipecolic acid. The resulting material was a powder. The resulting materials were flowable powders and remained flowable powders when left at ambient temperature. The Δ9-THC / histidine mixture resulted in a tacky solid. The XRPD patterns were obtained for the Δ9-THC / aspartame powder (FIG. 24), the Δ9-THC / caffeine powder (FIG. 25), the Δ9-THC / lactose powder (FIG. 26), and the Δ9-THC / L-pipecolic acid powder (FIG. 27). The XRPD patterns showed the presence of some crystalline powder former and an amorphous halo.

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Abstract

The invention relates to a solid Δ9-THC composition containing Δ9-THC and a powder former and having a molar ratio of Δ9-THC to powder former to form a flowable Δ9-THC powder. The powder former is selected from the group consisting of adenine, aspartame, caffeine, lactose, mannitol, nicotinamide, β-nicotinamide adenine dinucleotide, pipecolic acid, saccharin, aspartic acid, glutamic acid, glutamine, histidine, leucine, methionine, phenylalanine, proline, serine, tryptophan, valine, Epigallocatechin Gallate (EGCG), 2-Hydroxypropyl-beta-cyclodextrin (HPbCD), and Trimethyl-beta-cyclodextrin (TOMBC) and mixtures thereof. The invention also relates to methods of making a solid Δ9-THC composition of the invention. The Δ9-THC may be synthetic Δ9-THC or may be extracted Δ9-THC. The invention provides pharmaceutical or nutraceutical composition containing a solid Δ9-THC composition of the invention and a pharmaceutically- or nutraceutically-acceptable carrier where Δ9-THC is present in a pharmaceutically or nutraceutically effective amount. The invention also provides methods of treating a disease, disorder, or condition by administering to a patient in need thereof a therapeutically effective amount of a solid Δ9-THC composition. A solid Δ9-THC composition of the invention may also be incorporated into food and beverage products.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application claims priority to U.S. patent application 63 / 053,205, filed Jul. 17, 2020; to U.S. patent application 63 / 154,151, filed Feb. 26, 2021; and to U.S. patent application 63 / 154,153, filed Feb. 26, 2021. The disclosure of each application is incorporated herein by reference.BACKGROUND[0002]Cannabis has been a traditional drug and remedy in many cultures and for a long time. Cannabis was used for the treatment of various disorders ranging from asthma to migraine until the early 20th century. For an overview of natural cannabinoid compounds see David T. Brown ed., Cannabis, Hardwood Academic Publishers 1998, ISBN 90-5702-291-5. Tetrahydrocannabinol (THC), more specifically (−)-trans-Δ9-tetrahydrocannabinol (Δ9-THC) and its isomers, is the psychoactive component in cannabis. Recently, though it is a controlled substance, Δ9-THC has found therapeutic use as an appetite stimulant and an antiemetic. An example of a marketed Δ9-THC ...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/352A61K9/16A23L33/105A23L27/30
CPCA61K31/352A61K9/1617A23V2002/00A23L27/33A23L33/105A23L27/32A61K9/145A61K9/19A61K31/658A61K36/3482
Inventor RIGSBEE, EMILYJONAITIS, DAVID T.SCHULTHEISS, NATHAN
Owner CANNA CHEMISTRIES LLC
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