Chemistry:Nemertelline

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Nemertelline
Nemertelline skeletal structure
Names
Preferred IUPAC name
13,22:23,34:32,43-Quaterpyridine
Identifiers
3D model (JSmol)
ChemSpider
KEGG
MeSH Nemertelline
UNII
Properties
C20H14N4
Molar mass 310.360 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

Nemertelline is a neurotoxic tetra-pyridine compound originally found in the marine ribbon worm Amphiporus angulatus.[1] These worms produce a variety of toxins which are used both in hunting their prey and in defending themselves from predators.[2] Interest in potential application of this compound as an antifouling agent for boats and other marine installations has led to attempts to produce it synthetically by convenient routes.[3] Its toxicity is similar to nicotine in crustaceans but has no mammalian toxicity. It is similar to nicotelline in structure.[4]

References

  1. "Hoplonemertine worms -- a new source of pyridine neurotoxins". Experientia 32 (6): 684–6. June 1976. doi:10.1007/BF01919831. PMID 181266. 
  2. "Inhibition of barnacle larval settlement and crustacean toxicity of some hoplonemertine pyridyl alkaloids". Biomolecular Engineering 20 (4-6): 355–61. July 2003. doi:10.1016/S1389-0344(03)00049-2. PMID 12919820. 
  3. "An efficient two-step total synthesis of the quaterpyridine nemertelline". The Journal of Organic Chemistry 68 (26): 10178–80. December 2003. doi:10.1021/jo034805b. PMID 14682721. 
  4. "Hoplonemertine worms -- a new source of pyridine neurotoxins". Experientia 32 (6): 684–6. June 1976. doi:10.1007/BF01919831. PMID 181266.