Fluorinated empathogens
View Patent ↗Provided are fluorinated analogs of MDMA, including fluorinated 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 fluorinated empathogens and pharmaceutical compositions comprising the same. Methods of using the fluorinated empathogens, alone or in combination with other therapeutic agents, are provided. In some embodiments, fluorinated empathogens are used to treat CNS disorders, such as mental health conditions and neurodegenerative disorders.
1. A compound of any of Formulas (IIIA), (IIIC), (IIID), (IIIE), (IIIF), (IVA), (IVB), (IVC), (IVD), (IVE), or (IVF):
wherein each Y is independently protium (H) or fluorine (F), and
wherein at least one Y is fluorine (F) and the remaining Ys are protium (H);
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof;
provided that the compound is not
(3,4-methylenedioxy-N-trifluoroethylamphetamine, MDTFEA).
2. The compound of claim 1 , wherein the compound is any of Formulas (IIIA), (IIIC), (IIID), (IIIE), or (IIIF):
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.
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 (IIIC) 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 (IIID) 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), (IVC), (IVD), (IVE), or (IVF):
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.
9. The compound of claim 8 , 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 8 , 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 8 , which is a compound of Formula (IVC) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.
12. The compound of claim 8 , which is a compound of Formula (IVD) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.
13. The compound of claim 8 , which is a compound of Formula (IVE) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.
14. The compound of claim 8 , which is a compound of Formula (IVF) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.
15. A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 1 , and a pharmaceutically acceptable carrier, diluent, or excipient.