Crystalline N-methyl tryptamine derivatives
Crystalline N-methyl tryptamine derivatives, compositions containing those crystalline forms and their methods of use are disclosed. The crystalline N-methyl tryptamine derivatives according to the invention include crystalline N-methyl-N-propyltryptamine (MPT), crystalline N-methyl-N-isopropyltryptammonium fumarate (MiPT fumarate) and crystalline 4-hydroxy-N-methyl-N-isopropyltryptammonium fumarate monohydrate (HO-MiPT fumarate monohydrate).
1. Crystalline N-methyl-N-propyltryptamine (MPT) characterized by one or more of:
an orthorhombic, Pbca crystal system space group at a temperature of about 200 K;
unit cell dimensions a=13.5715 (11) Å, b=12.4352(10) Å, c=15.1627(12) Å, at a temperature of about 200 K;
or
an x-ray powder diffraction (XRPD) pattern having peaks at 11.7, 13.4 and 19.4° 2θ±0.2° 2θ.
2. Crystalline N-methyl-N-propyltryptamine (MPT) according to claim 1 , further characterized by an x-ray powder diffraction (XRPD) pattern substantially similar to FIG. 3 .
3. A composition comprising crystalline N-methyl-N-propyltryptamine (MPT) according to claim 1 and an excipient.
4. A method of treating a psychological disorder comprising the step of:
administering to a subject in need thereof a therapeutically effective amount of crystalline N-methyl-N-propyltryptamine (MPT) according to claim 1 .
5. A method of treating a psychological disorder comprising the step of:
administering to a subject in need thereof a therapeutically effective amount of crystalline N-methyl-N-propyltryptamine (MPT) according to claim 2 .
6. A method of treating a psychological disorder comprising the step of:
administering to a subject in need thereof a composition according to claim 3 .
7. Crystalline N-methyl-N-isopropyltryptammonium fumarate (MiPT fumarate) characterized by one or more of:
a monoclinic, P2 1 /c crystal system space group at a temperature of about 200 K;
unit cell dimensions a=9.852 (2) Å, b=12.789(2) Å, c=14.875 (3) Å, and β=106.932(7°) at a temperature of about 200 K;
or
an x-ray powder diffraction (XRPD) pattern having peaks at 11.9, 14.9 and 16.9° 2θ±0.2° 2θ.
8. Crystalline N-methyl-N-isopropyltryptammonium fumarate (MiPT fumarate) according to claim 7 , further characterized by an x-ray powder diffraction (XRPD) pattern substantially similar to FIG. 2 .
9. A composition comprising crystalline N-methyl-N-isopropyltryptammonium fumarate (MiPT fumarate) according to claim 7 and an excipient.
10. A method of treating a psychological disorder comprising the step of:
administering to a subject in need thereof a therapeutically effective amount of crystalline N-methyl-N-isopropyltryptammonium fumarate (MiPT fumarate) according to claim 7 .
11. A method of treating a psychological disorder comprising the step of:
administering to a subject in need thereof a therapeutically effective amount of crystalline N-methyl-N-isopropyltryptammonium fumarate (MiPT fumarate) according to claim 8 .
12. A method of treating a psychological disorder comprising the step of:
administering to a subject in need thereof a composition according to claim 9 .
13. Crystalline 4-hydroxy-N-methyl-N-isopropyltryptammonium fumarate monohydrate (HO-MiPT fumarate monohydrate) characterized by one or more of:
a monoclinic, C2/c crystal system space group at a temperature of about 200 K;
unit cell dimensions a=29.507 (3) Å, b=8.7445(8) Å, c=17.3659 (18) Å, and β=123.389(18°) at a temperature of about 200 K;
or
an x-ray powder diffraction (XRPD) pattern having peaks at 7.2, 13.4 and 18.0° 2θ±0.2° 2θ.
14. Crystalline 4-hydroxy-N-methyl-N-isopropyltryptammonium fumarate monohydrate (HO-MiPT fumarate monohydrate) according to claim 13 , further characterized by an x-ray powder diffraction (XRPD) pattern substantially similar to FIG. 11 .
15. A composition comprising crystalline 4-hydroxy-N-methyl-N-isopropyltryptammonium fumarate monohydrate (HO-MiPT fumarate monohydrate) according to claim 13 and an excipient.
16. A method of treating a psychological disorder comprising the step of:
administering to a subject in need thereof a therapeutically effective amount of crystalline 4-hydroxy-N-methyl-N-isopropyltryptammonium fumarate monohydrate (HO-MiPT fumarate monohydrate) according to claim 13 .
17. A method of treating a psychological disorder comprising the step of:
administering to a subject in need thereof a therapeutically effective amount of crystalline 4-hydroxy-N-methyl-N-isopropyltryptammonium fumarate monohydrate (HO-MiPT fumarate monohydrate) according to claim 14 .
18. A method of treating a psychological disorder comprising the step of:
administering to a subject in need thereof a composition according to claim 15 .