Therapeutic phenethylamine compositions and methods of use
There are disclosed deuterated 2C—X phenethylamine compounds, the use of such compounds in the treatment of diseases associated with a serotonin 5-HT 2 receptor, pharmaceutical compositions such as tablet compositions and kits containing the compounds, methods of delivering the compounds in a mist via inhalation, and methods of treating diseases or disorders associated with a serotonin 5-HT 2 receptor, such as central nervous system (CNS) disorders or psychological disorders with the compounds of the invention.
1. A compound having a structure of formula (I):
or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof,
wherein:
X 1 and X 2 are independently hydrogen or deuterium;
Y 1 and Y 2 are independently hydrogen or deuterium;
R 3 is hydrogen or deuterium,
R 4 is —SCF 3 ; and
each R a is independently a substituted or unsubstituted C 1 -C 6 alkyl,
wherein any position in the compound indicated as having deuterium has a minimum deuterium incorporation of at least 10 atom % at the site of deuteration.
2. The compound of claim 1 , wherein Y 1 and Y 2 are hydrogen.
3. The compound of claim 1 , wherein R 3 is hydrogen.
4. The compound of claim 1 , wherein X 1 and X 2 are hydrogen.
5. The compound of claim 1 , wherein X 1 and X 2 are deuterium.
6. The compound of claim 1 , wherein each R a is —CH 3 or —CD 3 .
7. The compound of claim 1 , having a structure of formula (II):
or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof,
wherein:
X 1 and X 2 are independently hydrogen or deuterium;
Y 1 and Y 2 are independently hydrogen or deuterium; and
R 4 is —SCF 3 .
8. The compound of claim 7 , wherein X 1 and X 2 are hydrogen.
9. The compound of claim 1 , having a structure of formula (IV):
or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof,
wherein:
Y 1 and Y 2 are independently hydrogen or deuterium;
R 4 is —SCF 3 ; and
each R a is independently a substituted or unsubstituted C 1 -C 6 alkyl.
10. The compound of claim 1 , which is selected from the group consisting of
or a pharmaceutically acceptable salt or solvate thereof.
11. A pharmaceutical composition, comprising the compound of claim 1 and a pharmaceutically acceptable excipient.
12. The pharmaceutical composition of claim 11 , which is formulated for oral administration.
13. The pharmaceutical composition of claim 11 , which is formulated for administration via inhalation.