Guanitoxin

Guanitoxin
Names
	IUPAC name (5S)-5-[(Dimethylamino)methyl]-1-{[hydroxy(methoxy)phosphoryl]oxy}-4,5-dihydro-1H-imidazol-2-amine
Identifiers
CAS Number	103170-78-1;
3D model (JSmol)	Interactive image;
ChemSpider	102921;
KEGG	C19998;
PubChem CID	114989;
UNII	4258P76E76;
CompTox Dashboard (EPA)	DTXSID20897217 ;
	InChI InChI=1S/C7H17N4O4P/c1-10(2)5-6-4-9-7(8)11(6)15-16(12,13)14-3/h6H,4-5H2,1-3H3,(H2,8,9)(H,12,13)/t6-/m1/s1 Key: FYXHGVMFJYHPFX-ZCFIWIBFSA-N;
	SMILES CN(C)C[C@H]1CN=C(N1OP(=O)(O)OC)N;
Properties
Chemical formula	C7H17N4O4P
Molar mass	252.211 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

Guanitoxin (GNT), formerly known as anatoxin-a(S) "Salivary"^[a],^[1] is a naturally occurring cyanotoxin commonly isolated from cyanobacteria (specifically of the genus Anabaena). It is a potent covalent acetylcholinesterase inhibitor, and thus a potent rapid acting neurotoxin which in cases of severe exposure can lead to death. Guanitoxin was first structurally characterized in 1989, and consists of a cyclic N-hydroxyguanidine organophosphate with a phosphate ester moiety.^[2]

Cite error: There are <ref group=lower-alpha> tags or {{efn}} templates on this page, but the references will not show without a {{reflist|group=lower-alpha}} template or {{notelist}} template (see the help page).

^ Fiore, Marli Fátima; de Lima, Stella Thomaz; Carmichael, Wayne W.; McKinnie, Shaun M.K.; Chekan, Jonathan R.; Moore, Bradley S. (2020). "Guanitoxin, re-naming a cyanobacterial organophosphate toxin". Harmful Algae. 92. Elsevier BV: 101737. doi:10.1016/j.hal.2019.101737. ISSN 1568-9883. PMID 32113603. S2CID 211725815.
^ Matsunaga, Shigeki; Moore, Richard E.; Niemczura, Walter P.; Carmichael, Wayne W. (1989). "Anatoxin-a(s), a potent anticholinesterase from Anabaena flos-aquae". Journal of the American Chemical Society. 111 (20). American Chemical Society (ACS): 8021–8023. doi:10.1021/ja00202a057. ISSN 0002-7863.

[Fiore_de_Lima_Carmichael_McKinnie_2020_p=101737-2] Fiore, Marli Fátima; de Lima, Stella Thomaz; Carmichael, Wayne W.; McKinnie, Shaun M.K.; Chekan, Jonathan R.; Moore, Bradley S. (2020). "Guanitoxin, re-naming a cyanobacterial organophosphate toxin". Harmful Algae. 92. Elsevier BV: 101737. doi:10.1016/j.hal.2019.101737. ISSN 1568-9883. PMID 32113603. S2CID 211725815.

[Matsunaga1989-3] Matsunaga, Shigeki; Moore, Richard E.; Niemczura, Walter P.; Carmichael, Wayne W. (1989). "Anatoxin-a(s), a potent anticholinesterase from Anabaena flos-aquae". Journal of the American Chemical Society. 111 (20). American Chemical Society (ACS): 8021–8023. doi:10.1021/ja00202a057. ISSN 0002-7863.

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