Synthesis and Biological Evaluation of 4‑Bromo-<i>N,N-</i>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-<i>N,N</i>-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-<i>N</i>,<i>N</i>-dimethyltryptamine (psilocin) and nonring-substituted analog, <i>N</i>,<i>N</i>-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.
Topics & conditions
Detected automatically by Psychedelic Commons from the title and abstract, not labels from the source. They may be incomplete.
Psychedelic Commons aggregates metadata from open sources and links back to the original. Rights remain with the authors and publishers. Something wrong with this record? Report a problem.