Domoic acid

Domoic acid

Names
IUPAC name (2S,3S,4S)-3-(Carboxymethyl)-4-[(1Z,3E,5R)-6-hydroxy-1,5-dimethyl-6-oxo-hexa-1,3-dienyl]pyrrolidine-2-carboxylic acid
Identifiers
CAS Number	14277-97-5 N
3D model (Jmol)	Interactive image
ChEBI	CHEBI:34727 N
ChemSpider	4445428 Y
ECHA InfoCard	100.159.099
IUPHAR/BPS	4181
PubChem CID	5282253
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 Y Key: VZFRNCSOCOPNDB-AOKDLOFSSA-N Y 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	311.33 g·mol−1
Density	1.273 g/cm3
Vapor pressure	2.62×10−16 mmHg (34.9 fPa)
Hazards
R-phrases	R20 R21 R22
S-phrases	S36 S37
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Domoic acid (DA) is a kainic acid analog neurotoxin that causes amnesic shellfish poisoning (ASP). It is produced by algae and accumulates in shellfish, sardines, and anchovies. When sea lions, otters, cetaceans, humans etc., then eat contaminated animals poisoning may result. Exposure to the biotoxin affects the brain, causing seizures, and possibly death.

There has been little use of domoic acid throughout history except for in Japan, where it has been used as an anthelmintic for centuries. Domoic acid was first isolated in 1959 from a species of red algae, Chondria armata, in Japan; commonly referred to as "doumoi" (in Tokunoshima's dialect word) or "hanayanagi". Poisonings in history have been rare, or undocumented; however, it is thought that the increase in human activities is resulting in an increasing frequency of toxic algal blooms along coastlines in recent years. Consequently, poisonings have been affecting sea animals, birds, and humans.

In 1961, seabirds attacked the Capitola area in California, and though it was never confirmed, they were thought to be under the influence of domoic acid.

In 1987, on Prince Edward Island, Canada, there was a shellfish poisoning resulting in 3 deaths. Blue mussels (Mytulis edulis) contaminated with domoic acid were blamed.

An incident in which domoic acid may have been involved took place on June 22, 2006, when a California brown pelican flew through the windshield of a car on the Pacific Coast Highway.

Domoic acid is a structural analog of kainic acid, proline, and endogenous excitatory neurotransmiter glutamate. Ohfune and Tomita, who wanted to investigate its absolute stereochemistry, were the first and only to synthesize domoic acid in 1982.