IP Library › Granted Patent US 10,959,961
Granted Patent B2
US 10,959,961 · App. 16/440,889 · Granted Mar 30, 2021

Methods of administering anionic cannabinoid molecules dissolved in water

Inventor: Douglas G. Metcalf (Erie, CO)
Assignee: Natural Extraction Systems, LLC
A61K31/05A61J1/00A61K9/0095A61K47/02A61K47/10
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Quick Facts
Patent No.
US 10,959,961
App. No.
16/440,889
Granted
Mar 30, 2021
Kind
B2
Abstract

Various aspects of this patent document relate to methods to administer compositions comprising anionic cannabinoid molecules.

Claims (76)

1. A method of consuming a cannabinoid, comprising:

providing a composition comprising an anionic cannabinoid molecule dissolved in water, in which the composition has a color;

contacting the composition with a Brønsted acid, in which contacting the composition with the Brønsted acid changes the color to either a different color or no color; and

consuming the composition after contacting the composition with the Brønsted acid, in which a human being consumes the composition by drinking it,

wherein the anionic cannabinoid molecule is selected from the group consisting of:

2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-3-hydroxy-5-pentylphenolate;

2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-3-en-1-yl]-3-hydroxy-5-pentylphenolate;

2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-5-pentyl-1,4-benzoquinone-3-oxide;

3-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-6-pentyl-1,2-benzoquinone-4-oxide;

2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-3-en-1-yl]-5-pentyl-1,4-benzoquinone-3-oxide;

3-[(1R,6R)-6-isopropenyl-3-methylcyclohex-3-en-1-yl]-6-pentyl-1,2-benzoquinone-4-oxide;

(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-oxide;

(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-1-oxide;

2-[(2E)-3,7-dimethylocta-2,6-dienyl]-3-hydroxy-5-pentylphenolate;

2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-3-hydroxy-5-propylphenolate;

2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-3-en-1-yl]-3-hydroxy-5-propylphenolate;

2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-5-propyl-1,4-benzoquinone-3-oxide;

3-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-6-propyl-1,2-benzoquinone-4-oxide;

2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-3-en-1-yl]-5-propyl-1,4-benzoquinone-3-oxide;

3-(1R,6R)-6-isopropenyl-3-methylcyclohex-3-en-1-yl]-6-propyl-1,2-benzoquinone-4-oxide;

(6aR,10aR)-6,6,9-trimethyl-3-propyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-oxide;

(6aR,10aR)-6,6,9-trimethyl-3-propyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-1-oxide; and

2-[(2E)-3,7-dimethylocta-2,6-dienyl]-3-hydroxy-5-propylphenolate.

2. The method of claim 1 , in which the anionic cannabinoid molecule is 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-3-hydroxy-5-pentylphenolate.

3. The method of claim 1 , comprising providing a hermetically-sealed container that contains the composition and unsealing the container to provide the composition.

4. The method of claim 3 , in which the hermetically-sealed container contains 25 milliliters to 800 milliliters of the composition.

5. The method of claim 3 , in which the composition comprises 50 micrograms to 500 milligrams of the anionic cannabinoid molecule.

6. The method of claim 3 , in which the hermetically-sealed container is a glass bottle, plastic bottle, or aluminum can.

7. The method of claim 3 , in which:

the hermetically-sealed container is physically associated with a label;

the label comprises an image of a reference color; and

the method comprises comparing the color of the anionic cannabinoid molecule dissolved in water to the reference color to either confirm the identity of the anionic cannabinoid molecule or confirm the approximate concentration of the anionic cannabinoid molecule in the composition.

8. The method of claim 1 , in which the color is purple.

9. The method of claim 1 , in which the composition has a pH, and the pH is 8.5 to 10.5.

10. The method of claim 1 , in which the composition comprises ethanol at a concentration of 5 parts per million to 500 parts per million by weight.

11. The method of claim 1 , in which the composition comprises a concentration of molecular oxygen, and the concentration of molecular oxygen is less than 50 micromolar.

12. The method of claim 11 , in which the composition comprises a concentration of molecular nitrogen, and the concentration of molecular nitrogen is less than 100 micromolar.

13. The method of claim 1 , comprising providing a hermetically-sealed container containing the composition and unsealing the container to provide the composition, in which:

the hermetically-sealed container is a glass bottle, plastic bottle, or aluminum can;

the container contains 25 milliliters to 800 milliliters of the composition;

the composition comprises 50 micrograms to 500 milligrams of the anionic cannabinoid molecule;

the composition has a pH; and

the pH of the composition is 8.5 to 10.5.

14. A method of consuming a cannabinoid, comprising:

providing a hermetically-sealed container that contains a composition, in which:

the hermetically-sealed container is a glass bottle, plastic bottle, or aluminum can; the container contains 25 milliliters to 800 milliliters of the composition; the composition comprises water and 50 micrograms to 500 milligrams of an anionic cannabinoid molecule; the anionic cannabinoid molecule is dissolved in the water; and the composition has a color;

unsealing the container;

contacting the composition with a Brønsted acid, in which contacting the composition with the Brønsted acid changes the color to either a different color or no color; and

consuming the composition after contacting the composition with the Brønsted acid, in which a human being consumes the composition by drinking it,

wherein the anionic cannabinoid molecule is selected from the group consisting of:

2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-3-hydroxy-5-pentylphenolate;

2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-3-en-1-yl]-3-hydroxy-5-pentylphenolate;

2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-5-pentyl-1,4-benzoquinone-3-oxide;

3-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-6-pentyl-1,2-benzoquinone-4-oxide;

2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-3-en-1-yl]-5-pentyl-1,4-benzoquinone-3-oxide;

3-[(1R,6R)-6-isopropenyl-3-methylcyclohex-3-en-1-yl]-6-pentyl-1,2-benzoquinone-4-oxide;

(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-oxide;

(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-1-oxide;

2-[(2E)-3,7-dimethylocta-2,6-dienyl]-3-hydroxy-5-pentylphenolate;

2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-3-hydroxy-5-propylphenolate;

2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-3-en-1-yl]-3-hydroxy-5-propylphenolate;

2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-5-propyl-1,4-benzoquinone-3-oxide;

3-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-6-propyl-1,2-benzoquinone-4-oxide;

2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-3-en-1-yl]-5-propyl-1,4-benzoquinone-3-oxide;

3-(1R,6R)-6-isopropenyl-3-methylcyclohex-3-en-1-yl]-6-propyl-1,2-benzoquinone-4-oxide;

(6aR,10aR)-6,6,9-trimethyl-3-propyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-oxide;

(6aR,10aR)-6,6,9-trimethyl-3-propyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-1-oxide; and

2-[(2E)-3,7-dimethylocta-2,6-dienyl]-3-hydroxy-5-propylphenolate.

15. The method of claim 14 , in which the anionic cannabinoid molecule is 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-3-hydroxy-5-pentylphenolate.

16. The method of claim 14 , in which the color is purple.

17. The method of claim 14 , in which the anionic cannabinoid molecule is 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-3-hydroxy-5-pentylphenolate; and the color is purple.

18. A method to change the color of a composition, comprising:

providing a container that contains a composition, in which: the composition comprises an anionic cannabinoid molecule dissolved in water; the anionic cannabinoid molecule is 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-3-hydroxy-5-pentylphenolate; the composition has a color; and the color is purple; and

contacting the composition with a Brønsted acid, in which contacting the composition with the Brønsted acid changes the color from purple to either a different color or no color.

19. The method of claim 18 , in which the Brønsted acid is hydronium, carbonic acid, or citric acid.

20. The method of claim 13 , in which the anionic cannabinoid molecule is 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-3-hydroxy-5-pentylphenolate.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 20, 2019
From: METCALF, DOUGLAS G.
To: NATURAL EXTRACTION SYSTEMS, LLC
Reel/Frame 050107/0553 →
Continuity (4)
Provisional Application 62780178 · Dec 14, 2018
Provisional Application 62787722 · Jan 2, 2019
Provisional Application 62812849 · Mar 1, 2019
Related Publication 20200188321A1 · Jun 18, 2020
Cited By (2)
US 12,349,706 US 12,484,606