Domoic acid

Domoic acid
Names
	Preferred IUPAC name (2S,3S,4S)-4-[(2Z,4E,6R)-6-Carboxyhepta-2,4-dien-2-yl]-3-(carboxymethyl)pyrrolidine-2-carboxylic acid
Identifiers
CAS Number	14277-97-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:34727 ;
ChEMBL	ChEMBL1232313 ;
ChemSpider	4445428 ;
ECHA InfoCard	100.159.099
EC Number	630-802-1;
IUPHAR/BPS	4181;
PubChem CID	5282253;
UNII	M02525818H ;
CompTox Dashboard (EPA)	DTXSID20274180 ;
	InChI InChI=1S/C15H21NO6/c1-8(4-3-5-9(2)14(19)20)11-7-16-13(15(21)22)10(11)6-12(17)18/h3-5,9-11,13,16H,6-7H2,1-2H3,(H,17,18)(H,19,20)(H,21,22)/b5-3+,8-4-/t9-,10+,11-,13+/m1/s1 Key: VZFRNCSOCOPNDB-AOKDLOFSSA-N ; InChI=1/C15H21NO6/c1-8(4-3-5-9(2)14(19)20)11-7-16-13(15(21)22)10(11)6-12(17)18/h3-5,9-11,13,16H,6-7H2,1-2H3,(H,17,18)(H,19,20)(H,21,22)/b5-3+,8-4-/t9-,10+,11-,13+/m1/s1 Key: VZFRNCSOCOPNDB-AOKDLOFSBM;
	SMILES O=C(O)[C@H]1NC[C@H](/C(=C\C=C\[C@H](C(=O)O)C)C)[C@@H]1CC(=O)O;
Properties
Chemical formula	C15H21NO6
Molar mass	311.334 g·mol−1
Density	1.273 g/cm3
Vapor pressure	2.62×10−16 mmHg (34.9 fPa)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H312, H332
Precautionary statements	P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Domoic acid (DA) is a kainic acid-type neurotoxin that causes amnesic shellfish poisoning (ASP).^[1] It is produced by algae and accumulates in shellfish, sardines, and anchovies. When sea lions, otters, cetaceans, humans, and other predators eat contaminated animals, poisoning may result. Exposure to this compound affects the brain, causing seizures, delirium and possibly death.^[2]

^ Clayden J, Read B, Hebditch KR (2005). "Chemistry of domoic acid, isodomoic acids, and their analogues". Tetrahedron. 24 (61): 5713–24. doi:10.1016/j.tet.2005.04.003.
^ "Domoic Acid Toxicity". The Marine Mammal Center. Retrieved 2 April 2015.

[Clayden_2005-1] Clayden J, Read B, Hebditch KR (2005). "Chemistry of domoic acid, isodomoic acids, and their analogues". Tetrahedron. 24 (61): 5713–24. doi:10.1016/j.tet.2005.04.003.

[2] "Domoic Acid Toxicity". The Marine Mammal Center. Retrieved 2 April 2015.

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