LSD derivatives, synthesis and method for treatment of diseases and disorders
LSD derivative compounds and polymorphs thereof, methods for their synthesis, compositions and treatment of diseases and disorders are described herein, the compounds having the structure of Formula I: including pharmaceutically acceptable salts, hydrates, solvates, tautomers, enantiomers, diastereomers, racemates, polymorphs or combinations thereof; wherein: R 1 to R 14 are each independently selected from H, or a substituted or unsubstituted hydrocarbon group and X is selected from a halo group.
1. A substantially pure crystalline form of a compound selected from:
wherein the compound has a Powder X-ray Diffraction (PXRD) pattern comprising a peak at 10.3°±0.2° (2θ).
2. The substantially pure crystalline form of the compound of claim 1 , wherein stereocenters of the compound are 5R and 8R.
3. The substantially pure crystalline form of the compound of claim 1 , wherein stereocenters of the compound are 5R and 8S.
4. The substantially pure crystalline form of the compound of claim 1 , wherein the compound is 2-bromo-LSD tartrate salt.
5. The substantially pure crystalline form of the compound of claim 4 , wherein the compound is (5R, 8R) 2-bromo-LSD hemi-D-tartrate salt.
6. The substantially pure crystalline form of the compound of claim 1 , wherein the compound is a substantially pure polymorph of (5R, 8R) 2-bromo-LSD hemi-D-tartrate salt.
7. The substantially pure crystalline form of the compound of claim 6 , wherein the PXRD pattern of the compound further comprises peaks at 4.7°±0.2° (2θ), 9.4°±0.2° (2θ), and 20.1°=0.2° (2θ).
8. The substantially pure crystalline form of the compound of claim 7 , wherein the compound has an optical rotation of about 0.30° to about 0.40°.
9. The substantially pure crystalline form of the compound of claim 6 , wherein the compound is substantially non-hallucinogenic.
10. The substantially pure crystalline form of the compound of claim 9 , wherein the compound promotes neural plasticity in neurons.
11. The substantially pure crystalline form of the compound of claim 9 , wherein the compound exhibits one or more of:
i) does not induce tolerance to the compound in a subject;
ii) is a moderate to potent pan-agonist across 5-HT1 receptor subtypes;
iiii) is a potent 5-HT6 receptor partial agonist;
iv) is a partial agonist at 5-HT2A and 5-HT1A receptor subtypes;
v) is not an agonist or is an antagonist if 5-HT2B receptor; and
vi) exhibits agonism at D2-like receptors.
12. A composition comprising one or more of the substantially pure crystalline form of the compound(s) of claim 1 .
13. A formulation comprising the composition of claim 12 and a pharmaceutically acceptable carrier, diluent or excipient.
14. The substantially pure crystalline form of the compound of claim 1 , wherein the compound is at least 98% pure.
15. The substantially pure crystalline form of the compound of claim 1 , wherein the compound is at least 99% pure.
16. The substantially pure crystalline form of the compound of claim 1 , wherein the compound is 100% pure.
17. A substantially pure crystalline form of a compound selected from:
wherein the compound has a Powder X-ray Diffraction (PXRD) pattern comprising a peak at 10.3°±0.2° (2θ) and another peak at one or more of 4.7°±0.2° (2θ), 9.4°±0.2° (2θ), and 20.1°±0.2° (2θ).
18. A substantially pure crystalline form of a compound selected from:
wherein the compound has a peak at 10.3°±0.2° (2θ) and d value of about 8.6 Å, optionally, another peak at one or more of 4.7°±0.2° (2θ) and d value of about 18.8 Å, and 9.4°±0.2° (2θ) and d value of about 9.4 Å.
19. A substantially pure crystalline form of a compound selected from:
wherein the compound comprising a Powder X-ray Diffraction (PXRD) pattern comprising one or more peaks at 10.3°±0.2° (2θ), 4.7°±0.2° (2θ), 9.4°±0.2° (2θ), and 20.1°±0.2° (2θ).