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

@article{Radulovi2012ANT,
  title={A novel toxic alkaloid from poison hemlock (Conium maculatum L., Apiaceae): identification, synthesis and antinociceptive activity.},
  author={Niko S. Radulovi{\'c} and Nevenka Dorđevi{\'c} and Marija S Deni{\'c} and Mariana Martins Gomes Pinheiro and Patr{\'i}cia Dias Fernandes and Fabio Boylan},
  journal={Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association},
  year={2012},
  volume={50 2},
  pages={274-9}
}
2-Pentylpiperidine, named conmaculatin, a novel volatile alkaloid related to coniine was identified from the renowned toxic weed Conium maculatum L. (Apiaceae). The structure of conmaculatin was corroborated by synthesis (8 steps starting from cyclohexanol, overall yield 12%). Conmaculatin's strong peripheral and central antinociceptive activity in mice was observed in a narrow dose range (10-20mg/kg). It was found to be lethal in doses higher than 20mg/kg.