5-methoxy-N,N-dimethyltryptamine crystalline forms
Described herein are crystalline fumarate salts having a Formula I, pharmaceutical formulations comprising the same, methods for their production, and uses thereof, Formula I comprising: wherein each R 1 is independently selected from protium and deuterium; each R 2 is independently selected from protium and deuterium; each R 3 is independently selected from protium and deuterium; and each R 4 is independently selected from protium and deuterium; and wherein the compound has a PXRD pattern comprising characteristic peaks at 19.2±0.2 and 24.7±0.2 degrees 2-theta.
1. A crystalline fumarate salt of a compound having a Formula I :
wherein:
each R 1 is independently selected from protium and deuterium;
each R 2 is independently selected from protium and deuterium;
each R 3 is independently selected from protium and deuterium; and
each R 4 is independently selected from protium and deuterium; and
wherein the crystalline fumarate salt has a PXRD pattern comprising characteristic peaks at 19.2±0.2 and 24.7±0.2 degrees 2-theta.
2. The crystalline fumarate salt of claim 1 , wherein the compound has a PXRD pattern further comprising characteristic peaks at 18.2±0.2 degrees 2-theta.
3. The crystalline fumarate salt of claim 1 , wherein one or more R 1 is deuterium.
4. The crystalline fumarate salt of claim 1 , wherein each R 1 is deuterium.
5. The crystalline fumarate salt of claim 1 , wherein one or more R 2 is deuterium.
6. The crystalline fumarate salt of claim 1 , wherein each R 2 is deuterium.
7. The crystalline fumarate salt of claim 1 , wherein one or more R 3 is protium.
8. The crystalline fumarate salt of claim 1 , wherein each R 3 is protium.
9. The crystalline fumarate salt of claim 1 , wherein one or more R 4 is protium.
10. The crystalline fumarate salt of claim 1 , wherein each R 4 is protium.
11. The crystalline fumarate salt of claim 1 , wherein each R 1 is protium, each R 2 is protium, each R 3 is protium, and each R 4 is protium.
12. The crystalline fumarate salt of claim 1 , wherein each R 1 is protium, one R 2 is protium and one R 2 is deuterium, each R 3 is protium, and each R 4 is protium.
13. The crystalline fumarate salt of claim 1 , wherein each R 1 is protium, each R 2 is deuterium, each R 3 is protium, and each R 4 is protium.
14. The crystalline fumarate salt of claim 1 , wherein each R 1 is deuterium, each R 2 is protium, each R 3 is protium, and each R 4 is protium.
15. The crystalline fumarate salt of claim 1 , wherein each R 1 is deuterium, each R 2 is deuterium, each R 3 is protium, and each R 4 is protium.
16. A method of producing the crystalline fumarate salt of claim 1 , comprising:
forming an ethanolic solution of a compound having Formula I;
contacting the ethanolic solution with fumaric acid to form a mixture;
stirring the mixture for between about 15 and about 45 minutes; and
cooling the mixture to between about 5° C. and about 0° C.
17. The method of claim 16 , further comprising adding seed crystals of the crystalline fumarate salt of claim 1 .
18. A method of treating a psychiatric or neurological disorder which is major depressive disorder or treatment resistant depression comprising administering to a patient in need thereof a pharmaceutically acceptable formulation comprising the crystalline fumarate salt of claim 1 .
19. The method of claim 18 , wherein:
each R 1 is protium, each R 2 is protium, each R 3 is protium, and each R 4 is protium;
each R 1 is protium, one R 2 is protium and one R 2 is deuterium, each R 3 is protium, and each R 4 is protium;
each R 1 is protium, each R 2 is deuterium, each R 3 is protium, and each R 4 is protium;
each R 1 is deuterium, each R 2 is protium, each R 3 is protium, and each R 4 is protium; or
each R 1 is deuterium, each R 2 is deuterium, each R 3 is protium, and each R 4 is protium.