Synthesis and Biological Evaluation of 4‑Bromo-N,N-dimethyltryptamine (4-Br-DMT): A Synthetic Building Block for Future Analog Development
Abstract
The ongoing psychedelic renaissance has prompted a renewed search for novel drugs based on modifying existing psychedelic motifs. In this study, a synthesis of 4-bromo-N,N-dimethyltryptamine (4-Br-DMT) was achieved and used as a late-stage intermediate for analog development. Specifically, we were able to synthesize and access novel molecules by forming carbon-carbon bonds at the C4 position using palladium cross-coupling reactions. Using the synthetic route described here will facilitate the rapid development of a library of tryptamines with novel 4-position substitutions to investigate structure-activity relationships (SARs) with serotonergic targets. Furthermore, the pharmacological target profile and biological effects of 4-Br-DMT were compared to the 4-hydroxy-N,N-dimethyltryptamine (psilocin) and nonring-substituted analog, N,N-dimethyltryptamine (DMT). Overall, the data indicate that 4-Br-DMT has a serotonergic profile without psychedelic-like effects in mice but has a reduced safety profile compared to psilocin and DMT.
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