IP Library Granted Patent US 12,419,855
Granted Patent B2
US 12,419,855 · App. 17/638,701 · Granted Sep 23, 2025

Compositions comprising cannabinoid ions that are dissolved in glycerol

Inventor: Douglas G. Metcalf (Boulder, CO)
Assignee: Natural Extraction Systems, LLC
A61K31/352A61K9/0014A61K9/0053A61K47/10C07D311/80
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Quick Facts
Patent No.
US 12,419,855
App. No.
17/638,701
Granted
Sep 23, 2025
Kind
B2
Abstract

Various aspects of this patent document relate to cannabinoid ions that are dissolved in glycerol, in which the cannabinoid ions are not carboxylates.

Claims (20)

1. A composition, comprising a liquid phase that comprises a solute and a solvent, wherein the solute is a cannabinoid ion; the cannabinoid ion is 3-(3,7-dimethylocta-2,6-diene-1-yl)-6-pentyl-1,2-benzoquinone-4-oxide; the solvent is glycerol; and the cannabinoid ion is dissolved in the glycerol.

2. The composition of claim 1 , comprising the glycerol at a concentration of at least 50 percent by weight.

3. The composition of claim 1 , comprising ethanol.

4. The composition of claim 1 , comprising water.

5. The composition of claim 1 , comprising a metal cation.

6. The composition of claim 5 , wherein the metal cation is sodium cation (“Na+”).

7. The composition of claim 5 , wherein the metal cation is potassium cation (“K+”).

8. The composition of claim 5 , comprising the metal cation and the cannabinoid ion at a molar ratio of at least 1:1 and no greater than 5:4.

9. The composition of claim 1 , comprising a concentration of the cannabinoid ion that is dissolved in the glycerol, wherein the cannabinoid ion has a conjugate acid that has a solubility in the liquid phase that is less than the concentration of the cannabinoid ion that is dissolved in the glycerol.

10. The composition of claim 1 , comprising a molecule and the cannabinoid ion at a molar ratio of at least 1:1,000,000 and less than 1:1, wherein the cannabinoid ion has a conjugate acid; and the molecule is the conjugate acid of the cannabinoid ion.

11. The composition of claim 1 , comprising the cannabinoid ion at a concentration of at least 1 gram per liter.

12. The composition of claim 1 , wherein the composition is formulated for oral administration to a human or an animal.

13. The composition of claim 1 , wherein the composition is formulated for topical administration to a human or an animal.

14. A medicament, comprising a composition according to claim 1 .

15. A method to administer a composition to a subject, comprising orally administering a composition according to claim 1 to the subject, wherein the subject is a human or an animal.

16. A method to administer a composition to a subject, comprising topically administering a composition according to claim 1 to the subject, wherein the subject is a human or an animal.

17. A composition, comprising a liquid phase that comprises a solute and a solvent, wherein the solute is a cannabinoid ion; the cannabinoid ion is 2-(3,7-dimethylocta-2,6-diene-1-yl)-3-hydroxy-5-pentylbenzene-1-oxide; the solvent is glycerol; and the cannabinoid ion is dissolved in the glycerol.

18. A method to administer a composition to a subject, comprising topically administering a composition according to claim 17 to the subject, wherein the subject is a human.

19. A composition, comprising a liquid phase that comprises a solute and a solvent, wherein the solute is a cannabinoid ion; the cannabinoid ion is 2-(3,7-dimethylocta-2,6-diene-1-yl)-5-pentyl-1,4-benzoquinone-3-oxide; the solvent is glycerol; and the cannabinoid ion is dissolved in the glycerol.

20. A method to administer a composition to a subject, comprising topically administering a composition according to claim 19 to the subject, wherein the subject is a human.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 25, 2025
From: METCALF, DOUGLAS G.
To: NATURAL EXTRACTION SYSTEMS, LLC
Reel/Frame 072922/0007 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 29, 2025
From: METCALF, DOUGLAS G.
To: NATURAL EXTRACTION SYSTEMS, LLC
Reel/Frame 072754/0804 →
Continuity (7)
Provisional Application 62971795 · Feb 7, 2020
Provisional Application 62950811 · Dec 19, 2019
Provisional Application 62935487 · Nov 14, 2019
Provisional Application 62928949 · Oct 31, 2019
Provisional Application 62923410 · Oct 18, 2019
Provisional Application 62892925 · Aug 28, 2019
Related Publication 20230000817A1 · Jan 5, 2023
References Cited (3)
EP 3351242A1 · 2018 [cited by applicant]
WO WO2017216362A1 · 2017 [cited by examiner]
WO 2019036243A1 · 2019 [cited by applicant]