The development of probe molecules that can be used to investigate G protein-coupled receptor (GPCR) pharmacology, trafficking and relationship with other GPCRs is an important and growing area of research. Here, we report the synthesis of analogs of the known selective serotonin (5-HT) 5-HT2C receptor (5-HT2CR) agonist WAY163909 which were designed to allow for the attachment of a second ligand, signaling or reporter molecules as well as immobilization agents to the parent molecule with the maintenance of agonist activity. This goal was accomplished by the synthesis of novel molecules in which sites a–d were modified and resulting compounds were analyzed pharmacologically in vitro.