title: A novel toxic alkaloid from poison hemlock (Conium maculatum L., Apiaceae): identification, synthesis and antinociceptive activity.
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.
authors: Department of Chemistry, Faculty of Science and Mathematics, University of Niš, Višegradska 33, 18000 Niš, Serbia. nikoradulovic@yahoo.com
authors: Niko
authors: N
authors: Radulović
authors: Nevenka
authors: N
authors: Dorđević
authors: Marija
authors: M
authors: Denić
authors: Mariana Martins Gomes
authors: MM
authors: Pinheiro
authors: Patricia Dias
authors: PD
authors: Fernandes
authors: Fabio
authors: F
authors: Boylan
mesh_terms: D000109:Acetylcholine / Q000633:toxicity; D000470:Alkaloids / Q000008:administration & dosage / Q000737:chemistry* / Q000494:pharmacology / Q000633:toxicity*; D000700:Analgesics / Q000008:administration & dosage / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity; D000818:Animals; D029982:Conium / Q000737:chemistry*; D004305:Dose-Response Relationship, Drug; D006358:Hot Temperature / Q000009:adverse effects; D008297:Male; D051379:Mice; D015394:Molecular Structure; D010146:Pain / Q000139:chemically induced / Q000188:drug therapy*; D010880:Piperidines / Q000008:administration & dosage / Q000737:chemistry* / Q000494:pharmacology / Q000633:toxicity*
chemical_list: C572623:2-pentylpiperidine; D000470:Alkaloids; D000700:Analgesics; D010880:Piperidines; D000109:Acetylcholine