Nemertelline

Nemertelline
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 ;
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

^ 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.
^ 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.
^ 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.
^ 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.

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[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.

[pmid181266-4] 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.

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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