5-Halotryptamines

5-Bromo-DMT, or 5-Br-DMT, also known as '5-bromo-N,N-dimethyltryptamine or by informal names like sea DMT or SpongeBob DMT', is a psychedelic drug and brominated indole alkaloid of the tryptamine family related to dimethyltryptamine (DMT). It is the 5-bromo derivative of DMT. The drug is naturally occurring in the sponges Smenospongia aurea and Smenospongia echina, as well as in Verongula rigida (0.00142% dry weight) alongside 5,6-dibromo-DMT (0.35% dry weight) and seven other alkaloids. It has been encountered as a novel designer drug.

Cipargamin (also known as KAE609 or NITD609) is a synthetic antimalarial compound belonging to the novel spiroindolone drug class. Developed by Novartis Institute for Tropical Diseases in Singapore, through a collaboration with the Genomics Institute of the Novartis Research Foundation (GNF), the Biomedical Primate Research Centre and the Swiss Tropical Institute, cipargamin represents a promising next-generation antimalarial drug currently undergoing Phase II clinical trials with a particular focus on safety evaluation. Cipargamin was awarded MMV Project of the Year 2009.

5-Fluoro-DMT, or 5-F-DMT, also known as '5-fluoro-N,N-dimethyltryptamine', is a psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT) and to other psychedelic tryptamines like 5-chloro-DMT and 5-bromo-DMT.

Flucindole (, ; developmental code name WIN-35150) is an antipsychotic of the tetrahydrocarbazolamine family with a tricyclic cyclized tryptamine structure that was never marketed. It is the 6,8-difluoro derivative of ciclindole. The drug is about 5 to 10times more potent than ciclindole both in vitro and in vivo.