Crystalline forms of nicotinamide riboside chloride

1. A method for preparing a crystalline form of a compound having the structure of formula (I):

comprising:

(a) providing a mixture of a compound of formula (I) in a first organic solvent; and

(b) crystallizing the compound of formula (I) from the mixture of a compound of formula (I) in a first organic solvent;

wherein the crystalline form is characterized by 20 values of 20.9±0.1, 21.6±0.1, 21.8±0.1, 23.6±0.1, and 24.4±0.1;

wherein the first organic solvent is methanol.

2. The method of claim 1 , wherein the mixture comprising the compound of formula (I) is a solution, and the step of crystallizing the compound of formula (I) from the mixture comprises bringing the solution to supersaturation to cause the compound of formula (I) to precipitate out of solution.

3. The method of claim 1 , further comprising isolating the crystalline form.

4. The method of claim 3 , wherein isolating the crystalline form comprises filtering the crystalline form from the mixture.

5. The method of claim 3 , further comprising washing the crystalline form with a second organic solvent.

6. The method of claim 5 , wherein the second organic solvent is selected from ethanol, acetone, and methyl tert-butyl ether.

7. The method of claim 3 , further comprising drying the crystalline form.

8. A method of improving cellular health, improving sleep quality, stimulating or increasing REM sleep, improving fertility, inducing ovulation, increasing sperm count, increasing lactation, or treating insomnia, desynchronosis, a circadian rhythm sleep disorder, or infertility in a subject, comprising administering to the subject a therapeutically effective amount of a crystalline form of a compound having the structure of formula (I):

wherein the crystalline form is characterized by 20 values of 20.9±0.1, 21.6±0.1, 21.8±0.1, 23.6±0.1, and 24.4±0.1.

9. A method of treating a motor neuron disease or ALS, or slowing or reversing the progression of motor neuron degeneration in a subject, comprising administering to the subject a therapeutically effective amount of a crystalline form of a compound having the structure of formula (I):

wherein the crystalline form is characterized by 20 values of 20.9±0.1, 21.6±0.1, 21.8±0.1, 23.6±0.1, and 24.4±0.1.

10. A method of treating kidney damage, acute kidney injury, or kidney disease, or increasing blood flow to the kidneys, comprising administering to the subject a therapeutically effective amount of a crystalline form of a compound having the structure of formula (I):

wherein the crystalline form is characterized by 20 values of 20.9±0.1, 21.6±0.1, 21.8±0.1, 23.6±0.1, and 24.4±0.1.

11. A method of treating liver damage or fatty liver, or decreasing the serum level of alanine transaminase (ALT) or aspartate transaminase (AST) in a subject, comprising administering to the subject a therapeutically effective amount of a crystalline form of a compound having the structure of formula (I):

wherein the crystalline form is characterized by 20 values of 20.9±0.1, 21.6±0.1, 21.8±0.1, 23.6±0.1, and 24.4±0.1.

12. The method of claim 1 , wherein the crystalline form is characterized by 20 values of 9.9±0.1, 18.4±0.1, 20.9±0.1, 21.6±0.1, 21.8±0.1, 23.6±0.1, 24.4±0.1, 29.4±0.1, 29.9±0.1, 30.5±0.1, and 33.5±0.1.

13. The method of claim 12 , wherein the crystalline form is characterized by 20 values of 9.9±0.1, 18.4±0.1, 20.9±0.1, 21.6±0.1, 21.8±0.1, 22.9±0.1, 23.6±0.1, 24.4±0.1, 25.2±0.1, 29.4±0.1, 29.9±0.1, 30.5±0.1, 31.9±0.1, 32.1±0.1, 33.5±0.1, 34.1±0.1, and 37.4±0.1.

14. The method of claim 13 , wherein the crystalline form is characterized by 20 values of 9.9±0.1, 15.6±0.1, 18.4±0.1, 18.5±0.1, 19.0±0.1, 20.9±0.1, 21.6±0.1, 21.8±0.1, 22.9±0.1, 23.6±0.1, 24.4±0.1, 25.2±0.1, 29.4±0.1, 29.9±0.1, 30.5±0.1, 31.5±0.1, 31.9±0.1, 32.1±0.1, 33.5±0.1, 34.0±0.1, 34.1±0.1, 36.5±0.1, and 37.4±0.1.

15. The method of claim 1 , wherein the crystalline form is characterized by 20 values of 20.87±0.10, 21.55±0.10, 21.79±0.10, 23.63±0.10, and 24.44±0.10.

16. The method of claim 15 , wherein the crystalline form is characterized by 20 values of 9.87±0.10, 18.36±0.10, 20.87±0.10, 21.55±0.10, 21.79±0.10, 23.63±0.10, 24.44±0.10, 29.35±0.10, 29.93±0.10, 30.47±0.10, and 33.51±0.10.

17. The method of claim 16 , wherein the crystalline form is characterized by 20 values of 9.87±0.10, 18.36±0.10, 20.87±0.10, 21.55±0.10, 21.79±0.10, 22.87±0.10, 23.63±0.10, 24.44±0.10, 25.25±0.10, 29.35±0.10, 29.93±0.10, 30.47±0.10, 31.87±0.10, 32.08±0.10, 33.51±0.10, 34.15±0.10, and 37.38±0.10.

18. The method of claim 17 , wherein the crystalline form is characterized by 20 values 9.87±0.10, 15.61±0.10, 18.36±0.10, 18.49±0.10, 19.01±0.10, 20.87±0.10, 21.55±0.10, 21.79±0.10, 22.87±0.10, 23.63±0.10, 24.44±0.10, 25.25±0.10, 29.35±0.10, 29.93±0.10, 30.47±0.10, 31.46±0.10, 31.87±0.10, 32.08±0.10, 33.51±0.10, 34.00±0.10, 34.15±0.10, 36.53±0.10, and 37.38±0.10.

19. The method of claim 1 , wherein the crystalline form has an XRD spectrum substantially as shown in FIG. 1 .

20. The method of claim 1 , wherein the purity of the crystalline form is 95%, 96%, 97%, 98%, 99%, 99.2%, 99.4%, 99.6%, 99.8% or higher.