Domoic acid

Domoic acid
Identifiers
CAS number	14277-97-5 N
PubChem	5282253
ChemSpider	4445428 Y
ChEMBL	CHEMBL420720 N
Jmol-3D images	Image 1
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
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
Properties
Molecular formula	C15H21NO6
Molar mass	311.3303 g/mol
Density	1.273 g/cm3
Boiling point	607.2 degrees Celsius at 760 mmHg (101.3 kPa)
Vapor pressure	2.62×10−16 mmHg (34.9 fPa) at 25 °C
Hazards
R-phrases	R20 R21 R22
S-phrases	S36 S37
Flash point	321°C
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Domoic acid (DA), the neurotoxin that causes amnesic shellfish poisoning (ASP), also known as zombie acid, is a kainic acid analog, heterocyclic amino acid associated with certain harmful algal blooms.

Occurrence

In 1958, domoic acid was originally isolated from the red alga called "doumoi" or "hanayanagi" (Chondria armata) in Japan. "Doumoi" is used as an anthelmintic in Tokunoshima, Kagoshima. Domoic acid is also produced by diatoms of the genus Pseudo-nitzschia and the species Nitzschia navis-varingica.

Pseudo-nitzschia multiseries loses most of its ability to produce domoic acid when it is cultured axenically. However, domoic acid production recovers when bacteria from the original culture are reintroduced to axenic cultures, indicating a bacterial association with domoic acid production in this species.

The increasing frequency and geographic extent of toxic algal blooms along populated coastlines is generally attributed to human activities.

Chemistry

Domoic acid is a structural analog of kainic acid and proline.

Toxicology

Considerable recent research has been carried out by the Marine Mammal Center and other scientific centers on the association of domoic acid-producing harmful algal blooms and neurological damage in marine mammals of the Pacific Ocean.

Domoic acid can bioaccumulate in marine organisms such as shellfish, anchovies, and sardines that feed on the phytoplankton known to produce this toxin. DA can accumulate in high concentrations in the tissues of these plankton feeders when the toxic phytoplankton itself is high in concentration in the surrounding waters.

In mammals, including humans, domoic acid acts as a neurotoxin, causing short-term memory loss, brain damage and, in severe cases, death. DA-producing algal blooms are associated with the phenomenon of amnesic shellfish poisoning (ASP). In marine mammals, domoic acid typically causes seizures and tremors. In the brain, domoic acid especially damages the hippocampus and amygdaloid nucleus. It damages the neurons by activating AMPA and kainate receptors, causing an influx of calcium. Although calcium flowing into cells is a normal event, the uncontrolled increase of calcium causes the cell to degenerate. Because the hippocampus may be severely damaged, short-term memory loss occurs.

See also

1. Harmful algal blooms
2. Pseudo-nitzschia

External links

• Domoic Acid and Pseudo-nitzschia References at Fisheries and Oceans Canada
• Amnesic Shellfish Poisoning, Domoic Acid, and Pseudo-nitzschia links at the ISSHA website
• Domoic acid at IPCS INCHEM
• DOMOIC ACID - A MAJOR CONCERN TO WASHINGTON STATE’S SHELLFISH LOVERS at Washington Department of Fish and Wildlife