Synthesis of Psilocin, Psilocybin and 5‐MeO‐DMT Succinate, All Labelled With Carbon‐14 at the Indole 2‐Position
Journal of Labelled Compounds and Radiopharmaceuticals July 1, 2025 Rodney D. Brown, Niall M. Hamilton, Connor Mallon et al. 1 citation
Three new radiolabelled versions of the psychedelic compounds psilocin, psilocybin, and 5-MeO-DMT were synthesized, each with carbon-14 at the 2-position of the indole ring. The synthesis used a common route: attaching the dimethylaminoethyl side chain to substituted indole intermediates via oxalyl chloride, dimethylamine, and lithium aluminium hydride reduction. Psilocybin-2-14C at 234 μCi/mg showed limited stability, but a 5.5-fold dilution with unlabelled psilocybin maintained >97.5% radiochemical purity after one month at ≤−70°C. 5-MeO-DMT-2-14C succinate at 173 μCi/mg remained 98.0% pure after six months at ≤−70°C, supporting long-term studies. These labelled compounds enable in vivo pharmacokinetic and metabolic studies of psychedelic tryptamines, aiding ADME and mass balance research for potential regulatory approval in treating depression, anxiety, and PTSD.