Crystalline psilacetin derivatives
The disclosure relates to crystalline psilacetin derivatives, compositions containing those crystalline derivatives, and methods of treatment using them. The crystalline psilacetin derivatives include crystalline 4-acetoxy-N-methyl-N-ethyltryptammonium (4-AcO-MET) hydrofumarate (“crystalline 4-AcO-MET hy-drofumarate”), crystalline 4-acetoxy-N-methyl-N-allyltryptammonium (4-AcO-MALT) hydrofumarate (“crystalline 4-AcO-MALT hydrofumarate”), and crystalline 4-acetoxy-N,N-diallyltryptammonium (4-AcO-DALT) fumarate fumaric acid (“crystalline 4-AcO-DALT fumarate fumaric acid”).
1. A crystalline psilacetin derivative selected from the group consisting of crystalline 4-acetoxy-N-methyl-N-ethyltryptammonium (4-AcO-MET) hydrofumarate, crystalline 4-acetoxy-N-methyl-N-allyltryptammonium (4-AcO-MALT) hydrofumarate, and crystalline 4-acetoxy-N,N-diallyltryptammonium (4-AcO-DALT) fumarate fumaric acid.
2. A composition comprising a crystalline psilacetin derivative according to claim 1 and an excipient.
3. A composition comprising a crystalline psilacetin derivative according to claim 1 and a second component selected from (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) one or two purified cannabinoids and (d) a purified terpene.
4. A method of treating a psychological disorder comprising the step of:
administering to a subject in need thereof a therapeutically effective amount of a crystalline psilacetin derivative according to claim 1 .
5. A method of treating a psychological disorder comprising the step of:
administering to a subject in need thereof a composition according to claim 2 .
6. A method of treating inflammation and/or pain comprising the step of:
administering to a subject in need thereof a therapeutically effective amount of a crystalline psilacetin derivative according to claim 1 .
7. A method of treating inflammation and/or pain comprising the step of:
administering to a subject in need thereof a composition according to claim 2 .
8. A method of treating a psychological disorder comprising the step of:
administering to a subject in need thereof a composition according to claim 3 .
9. A method of treating inflammation and/or pain comprising the step of:
administering to a subject in need thereof a composition according to claim 3 .
10. A composition of claim 2 wherein the crystalline psilacetin derivative is crystalline 4-acetoxy-N-methyl-N-ethyltryptammonium (4-AcO-MET) hydrofumarate.
11. A composition of claim 2 wherein the crystalline psilacetin derivative is crystalline 4-acetoxy-N-methyl-N-allyltryptammonium (4-AcO-MALT) hydrofumarate.
12. A composition of claim 2 wherein the crystalline psilacetin derivative is crystalline 4-acetoxy-N,N-diallyltryptammonium (4-AcO-DALT) fumarate fumaric acid.
13. A composition of claim 3 wherein the crystalline psilacetin derivative is crystalline 4-acetoxy-N-methyl-N-ethyltryptammonium (4-AcO-MET) hydrofumarate.
14. A composition of claim 3 wherein the crystalline psilacetin derivative is crystalline 4-acetoxy-N-methyl-N-allyltryptammonium (4-AcO-MALT) hydrofumarate.
15. A composition of claim 3 wherein the crystalline psilacetin derivative is crystalline 4-acetoxy-N,N-diallyltryptammonium (4-AcO-DALT) fumarate fumaric acid.
16. A crystalline psilacetin derivative of claim 1 wherein the crystalline psilacetin derivative is crystalline 4-acetoxy-N-methyl-N-ethyltryptammonium (4-AcO-MET) hydrofumarate characterized by:
a monoclinic, P2 1 crystal system space group at a temperature of about 200 K,
unit cell dimensions a=7.9555 (4) Å, b=13.3696 (7) Å, c=9.9708 (5) Å, and β=112.874 (2)°,
an XRPD having peaks at 11.7, 16.4, and 20.4°2θ±0.2°2θ, or
an XRPD pattern substantially similar to FIG. 4 .
17. A crystalline psilacetin derivative of claim 1 wherein the crystalline psilacetin derivative is crystalline 4-acetoxy-N-methyl-N-allyltryptammonium (4-AcO-MALT) hydrofumarate characterized by:
a monoclinic, P2 1 crystal system space group at a temperature of about 297 K,
unit cell dimensions a=7.9702 (4) Å, b=14.1788 (7) Å, c=9.8035 (5) Å, and β=113.394 (2)°,
an XRPD having peaks at 11.6, 15.9, and 17.5°2θ±0.2°2θ, or
an XRPD pattern substantially similar to FIG. 8 .
18. A crystalline psilacetin derivative of claim 1 wherein the crystalline psilacetin derivative is crystalline 4-acetoxy-N,N-diallyltryptammonium (4-AcO-DALT) fumarate fumaric acid characterized by:
a monoclinic, P2/c crystal system space group at a temperature of about 297 K,
unit cell dimensions a=23.6642 (19) Å, b=8.4204 (18) Å, c=23.4002 (18) Å, and β=111.614 (6)°,
an XRPD having peaks at 9.1, 14.7, and 19.9°2θ±0.2°2θ, or
an XRPD pattern substantially similar to FIG. 12 .