Nemertelline

Nemertelline

Nemertelline skeletal structure
Names
Preferred IUPAC name 13,22:23,34:32,43-Quaterpyridine
Identifiers
CAS Number	59697-14-2
3D model (JSmol)	Interactive image
ChemSpider	2305572
KEGG	C17016
MeSH	Nemertelline
PubChem CID	3042423
UNII	45M2T55WTP  Y
CompTox Dashboard (EPA)	DTXSID80208401
InChI InChI=1S/C20H14N4/c1-4-16(13-21-8-1)19-12-15(7-11-23-19)18-6-3-10-24-20(18)17-5-2-9-22-14-17/h1-14H Key: SWWRILUGNLIYGG-UHFFFAOYSA-N
SMILES C1=CN=CC(=C1)C1=CC(=CC=N1)C1=C(N=CC=C1)C1=CC=CN=C1
Properties
Chemical formula	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

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. Kem WR, Scott KN, Duncan JH (June 1976). "Hoplonemertine worms -- a new source of pyridine neurotoxins". Experientia. 32 (6): 684–6. doi:10.1007/BF01919831. PMID   181266.
2. Kem WR, Soti F, Rittschof D (July 2003). "Inhibition of barnacle larval settlement and crustacean toxicity of some hoplonemertine pyridyl alkaloids". Biomolecular Engineering. 20 (4–6): 355–61. doi:10.1016/S1389-0344(03)00049-2. PMID   12919820.
3. Bouillon A, Voisin AS, Robic A, Lancelot JC, Collot V, Rault S (December 2003). "An efficient two-step total synthesis of the quaterpyridine nemertelline". The Journal of Organic Chemistry. 68 (26): 10178–80. doi:10.1021/jo034805b. PMID   14682721.
4. Kem WR, Scott KN, Duncan JH (June 1976). "Hoplonemertine worms -- a new source of pyridine neurotoxins". Experientia . 32 (6): 684–6. doi:10.1007/BF01919831. PMID   181266.