A novel toxic alkaloid from poison hemlock (Conium maculatum L., Apiaceae): identification, synthesis and antinociceptive activity |
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| Authors: | Niko Radulović Nevenka Đorđević Marija Denić Mariana Martins Gomes Pinheiro Patricia Dias Fernandes Fabio Boylan |
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| Affiliation: | 1. Department of Chemistry, Faculty of Science and Mathematics, University of Niš, Višegradska 33, 18000 Niš, Serbia;2. Laboratório de Farmacologia da Inflamação e do Óxido Nítrico, Instituto de Ciências Biomédicas, Universidade Federal do Rio de Janeiro, Avenida Carlos Chagas, 373-bl. K, Rio de Janeiro, RJ, Brazil;3. Panoz Institute, School of Pharmacy and Pharmaceutical Sciences, Trinity College Dublin 23, Westland Row, Dublin 2, Ireland |
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| Abstract: | 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. |
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| Keywords: | Conium maculatum L. 2-Pentylpiperidine Volatile alkaloid Synthesis Antinociceptive activity Toxicity |
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