Deuterated empathogens
View Patent ↗Provided are deuterated analogs of MDMA, including deuterated empathogens. In some embodiments, such compounds are monoamine releasers or inhibit monoamine transporters. In some aspects, features of the compounds provide stability, such as metabolic stability, and efficacy. Also provided are methods for the preparation of deuterated empathogens and pharmaceutical compositions comprising the same. Methods of using the deuterated empathogens, alone or in combination with other therapeutic agents, are provided. In some embodiments, deuterated empathogens are used to treat CNS disorders, such as mental health conditions and neurodegenerative disorders.
1. A compound of any of Formulas (IIIA), (IIIB), (IIIC), (IIIE), (IIIF), (IVA), (IVB), or (IVC):
wherein each Y is independently protium (H) or deuterium (D), and
wherein at least one Y is deuterium (D) and the remaining Ys are protium (H);
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof;
provided that the compound is not
2. The compound of claim 1 , wherein the compound is any of Formulas (IIIA), (IIIB), (IIIC), (IIIE), or (IIIF):
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof;
provided that the compound is not
3. The compound of claim 2 , which is a compound of Formula (IIIA) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.
4. The compound of claim 2 , which is a compound of Formula (IIIB) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.
5. The compound of claim 2 , which is a compound of Formula (IIIC) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.
6. The compound of claim 2 , which is a compound of Formula (IIIE) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.
7. The compound of claim 2 , which is a compound of Formula (IIIF) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.
8. The compound of claim 1 , wherein the compound is any of Formulas (IVA), (IVB), or (IVC):
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof, provided that the compound is not
9. The compound of claim 2 , which is a compound of Formula (IVA) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.
10. The compound of claim 2 , which is a compound of Formula (IVB) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.
11. The compound of claim 4 , which is a compound of Formula (IVC) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.
12. A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 1 , and a pharmaceutically acceptable carrier, diluent, or excipient.
13. The pharmaceutical composition of claim 12 , wherein the compound is either of
14. The pharmaceutical composition of claim 12 , wherein the compound is either of