COMPOSITIONS, CONTAINERS, AND METHODS RELATED TO FLAVYLIUM EXCIPIENTS

Abstract

Various aspects of this disclosure relate to a composition, comprising a liquid phase that consists of chemical species that comprise tetrahydrocannabinol, one or more flavyliums, and a solvent, wherein each chemical species of the liquid phase has a concentration in the liquid phase; the tetrahydrocannabinol is dissolved in the liquid phase at a concentration of at least 0.1 percent and no greater than 8 percent by mass; each flavylium of the one or more flavyliums is a substituted 2-phenylchromenylium that consists of carbon, hydrogen, and oxygen atoms; the solvent is miscible with water; and the liquid phase comprises the solvent at a greater concentration by mass than any other chemical species of the liquid phase.

Claims

1. A composition, comprising a liquid phase that consists of chemical species that comprise tetrahydrocannabinol, one or more flavyliums, and a solvent, wherein each chemical species of the liquid phase has a concentration in the liquid phase; the tetrahydrocannabinol is dissolved in the liquid phase at a concentration of at least 0.1 percent and no greater than 8 percent by mass; each flavylium of the one or more flavyliums is a substituted 2-phenylchromenylium that consists of carbon, hydrogen, and oxygen atoms; the solvent is miscible with water; and the liquid phase comprises the solvent at a greater concentration by mass than any other chemical species of the liquid phase.

2. The composition of claim 1, wherein each flavylium of the one or more flavyliums is a substituted 2-phenylchromenylium, in which 0, 1, or 2 hydrogen atoms of a 2-phenylchromenylium cation are independently substituted with a sugar such that the flavylium is an aglycoside, 3-O-glycoside, or 3,5-O-diglycoside, respectively; each sugar is selected from 6-O-acetylglucose, 6-O-(para-caffeoyl)glucose, 6-O-(para-coumaroyl)glucose, arabinose, galactose, glucose, rhamnose, and rutinose; and other hydrogen atoms of the 2-phenylchromenylium cation are optionally and independently substituted with hydroxy or methoxy.

3. The composition of claim 1, wherein each flavylium of the one or more flavyliums is a substituted 2-phenylchromenylium selected from 5-desoxymalvidin, 5-desoxypeonidin, 6-hydroxycyanidin, antirrhinin, apigeninidin, aurantinidin, callistephin, capensinidin, chrysanthemin, columnidin, cyanidin, cyanidin 3-O-(6-acetyl)glucoside, cyanidin 3-O-(6-p-coumaroyl)glucoside, cyanin, delphin, delphinidin, delphinidin 3-O-(6-acetyl)glucoside, delphinidin 3-O-(6-p-coumaroyl)glucoside, delphinidin 3-O-rhamnoside, diosmetinidin, europinidin, fisetinidin, gesneridin, guibourtinidin, hirsutidin, ideain, kaempferidinidin, luteolinidin, malvidin, malvidin 3-O-(6-acetyl)glucoside, malvidin 3-O-(6-p-caffeoyl)glucoside, malvidin 3-O-(6-p-coumaroyl)glucoside, malvin, myrtillin, oenin, pelargonidin, pelargonin, peonidin, peonidin acetyl)glucoside, peonidin 3-O-(6-p-caffeoyl)glucoside, peonidin 3-O-(6-p-coumaroyl)glucoside, peonidin 3-O-glucoside, peonin, petunidin, petunidin 3-O-(6-acetyl)galactoside, petunidin 3-O-(6-acetyl)glucoside, petunidin 3-O-(6-p-coumaroyl)glucoside, petunidin 3-O-arabinoside, petunidin 3-O-galactoside, petunidin 3-O-glucoside, petunidin 3-O-rhamnoside, petunidin 3-O-rutinoside, petunin, primulin, pulchellidin, pulchellidin 3-O-glucoside, pulchellidin 3-rhamnoside, robinetinidin, rosinidin, tricetinidin, and tulipanin.

4. The composition of claim 1, wherein the one or more flavyliums comprise one or more substituted 2-phenylchromenyliums, in which 0, 1, or 2 hydrogen atoms of a 2-phenylchromenylium cation are independently substituted with a sugar such that the flavylium is an aglycoside, 3-O-glycoside, or 3,5-O-diglycoside, respectively; each sugar is selected from arabinose, galactose, glucose, rhamnose, and rutinose; and other hydrogen atoms of the 2-phenylchromenylium cation are optionally and independently substituted with hydroxy or methoxy.

5. The composition of claim 1, wherein each flavylium of the one or more flavyliums is a substituted 2-phenylchromenylium selected from 5-desoxymalvidin, 5-desoxypeonidin, 6-hydroxycyanidin, antirrhinin, apigeninidin, aurantinidin, callistephin, capensinidin, chrysanthemin, columnidin, cyanidin, cyanin, delphin, delphinidin, delphinidin 3-O-rhamnoside, diosmetinidin, europinidin, fisetinidin, gesneridin, guibourtinidin, hirsutidin, ideain, kaempferidinidin, luteolinidin, malvidin, malvin, myrtillin, oenin, pelargonidin, pelargonin, peonidin, peonidin 3-O-glucoside, peonin, petunidin, petunidin 3-O-arabinoside, petunidin 3-O-galactoside, petunidin 3-O-glucoside, petunidin 3-O-rhamnoside, petunidin 3-O-rutinoside, petunin, primulin, pulchellidin, pulchellidin 3-O-glucoside, pulchellidin 3-rhamnoside, robinetinidin, rosinidin, tricetinidin, and tulipanin.

6. The composition of claim 1, wherein each flavylium of the one or more flavyliums is a substituted 2-phenylchromenylium selected from callistephin, chrysanthemin, myrtillin, oenin, peonidin 3-O-glucoside, petunidin 3-O-glucoside, and pulchellidin 3-O-glucoside.

7. The composition of claim 1, wherein each flavylium of the one or more flavyliums is a substituted 2-phenylchromenylium selected from 3-deoxyanthocyanidin, 5-desoxymalvidin, 5-desoxypeonidin, 6-hydroxycyanidin, apigeninidin, aurantinidin, capensinidin, columnidin, cyanidin, delphinidin, diosmetinidin, europinidin, fisetinidin, gesneridin, guibourtinidin, hirsutidin, kaempferidinidin, luteolinidin, malvidin, pelargonidin, peonidin, petunidin, pulchellidin, robinetinidin, rosinidin, and tricetinidin.

8. The composition of claim 1, wherein the liquid phase comprises glycerol at a concentration of at least 20 percent and no greater than 93 percent by mass.

9. The composition a of claim 1, wherein the liquid phase comprises ethanol at a concentration of at least 5 percent and no greater than 40 percent by mass.

10. The composition of claim 1, wherein the liquid phase comprises water at a concentration of at least 0.5 percent and no greater than 20 percent by mass.

11. The composition of claim 1, comprising tart cherry powder, wherein at least one flavylium of the one or more flavyliums is derived from the tart cherry powder.

12. The composition of claim 1, wherein each flavylium of the one or more flavyliums has a concentration in the liquid phase; the one or more flavyliums have a combined concentration in the liquid phase that is equal to the sum of the concentrations of each flavylium in the liquid phase; and the liquid phase has a ratio by mass of the combined concentration of the one or more flavyliums to the concentration of the tetrahydrocannabinol that is greater than 1:1 (flavyliums:tetrahydrocannabinol).

13. The composition of claim 1, wherein the composition is formulated for human consumption; the composition is formulated for oral administration; and the liquid phase comprises at least 4 kilocalories and no greater than 5 kilocalories of nutritional energy per gram.

14. The composition of claim 1, wherein the liquid phase comprises a concentration of ethyl oxonium and a concentration of ethoxide at a ratio of at least 100:1 and no greater than 10,000:1 by mole.

15. The composition of claim 1, wherein the composition is formulated for human consumption; the composition is formulated for oral administration; and the composition if formulated such that a portion of the tetrahydrocannabinol of the composition is absorbed into the epithelial lining of the gastrointestinal tract of a human following oral administration by the human before the composition enters the stomach of the human.

16. The composition of claim 1, wherein the composition is formulated for human consumption; the composition is formulated for oral administration; the composition comprises an oral bioavailability of at least 10 percent; and the oral bioavailability is a percentage of the tetrahydrocannabinol of the composition that would be expected to enter the blood of a human following oral administration by the human to the human.

17. The composition of claim 1, wherein the composition is formulated for human consumption; the composition is formulated for oral administration; the composition comprises a Tmax that is no greater than 30 minutes; and the Tmax is the time to achieve a maximum blood concentration of tetrahydrocannabinol in a human following oral administration.

18. The composition of claim 1, wherein the composition is a spray; and the spray comprises at least 800 micrograms and no greater than 1.2 milligrams of the tetrahydrocannabinol.

19. The composition of claim 1, wherein the composition is a spray; and the spray comprises at least 80 microliters and no greater than 190 microliters of the liquid phase.

20. The composition of claim 1, wherein the composition is an aerosol spray.

Description

EXEMPLIFICATION

[0243] The following example illustrates a commercially-relevant embodiment, and the example does not limit the disclosure or any patent claim that matures from this disclosure.

[0244] The Example. The manufacture of an oral tetrahydrocannabinol spray comprising flavylium excipients.

[0245] 3.4 grams of marijuana distillate and 18 grams of tart cherry powder (BulkSupplements.com, Nevada, United States) were dissolved in 116 grams of 190 proof ethanol and 47 grams of propylene glycol. The marijuana distillate contained 82 percent tetrahydrocannabinol, and the tart cherry powder contained about 2 percent flavyliums derived Prunus cerasus fruit. 263 grams of glycerol was then added to the solution, and the solution was mixed for 10 minutes.

[0246] The solution described in the preceding paragraph was loaded into 15 milliliter spray bottles for oral administration. Each spray bottle produced a spray containing approximately 150 microliters of a liquid phase in which each 150 microliter spray contained approximately 1 milligram of tetrahydrocannabinol.