A novel toxic alkaloid from poison hemlock (Conium maculatum L., Apiaceae): Identification, synthesis and antinociceptive activity

► 2-Pentylpiperidine, named conmaculatin, was identified from the essential oil of Conium maculatum L. ► The new alkaloid was synthesized in 8 steps from cyclohexanol and in 12% total yield. ► The biosynthesis of the alkaloid should follow the acetate pathway, known for coniine. ► Conmaculatin was found to be lethal to mice in doses higher than 20 mg/kg. ► 2-Pentylpiperidine showed a strong antinociceptive effect in a dose dependent manner.