SEP-225,289 is an antidepressant drug derived from the active enantiomer of sibutramine, which was being developed by Sepracor. It is a so-called triple reuptake inhibitor (TRI).[1][2][3]

Similarity to Sibutramine

As can be seen by analyzing the molecular structure, SEP-225289 is a single isomer of sibutramine that has been N-dimethylated to yield a primary amine compound. According to one source, makes the compound stronger as a catecholaminergic relative to its actions on serotonin.[4] Apparently, both isomers of sibutramine are active but it is the R enantiomer that is held accountable for its anorectic action.


Further reading

Original Sibutramine patents
  • U.S. Patent 4,746,680
  • U.S. Patent 4,806,570
Liming Shao Patent
  • US application 2007203111, Shao L, Wang F, Malcolm SC, Hewitt MC, Bush LR, Ma J, Varney MA, Campbell U, Engel SR, Hardy LW, Koch P, Campbell JE, "Cycloalkylamines as monoamine reuptake inhibitors", published 2007-08-30, assigned to Sepracor Inc. 
Asymmetry Patent
  • US patent 7129378, Han X, Krishnamurthy D, Senanayake CH, Lu Z-H, "Method of preparing amine stereoisomers", published 2005-07-28, assigned to Apsinterm LLC