Domoic acid
50555
221555835
2008-06-25T01:08:57Z
Meodipt
1170531
{{Chembox new
| ImageFile = domoic-acid.png
| ImageSize = 200px
| IUPACName = (''2S,3S,4S'')-4-[(''2Z,4E'')-6-carboxyhepta-2,4-dien-2-yl]-3-​(carboxymethyl)pyrrolidine-2-carboxylic acid
| OtherNames =
| Section1 = {{Chembox Identifiers
| CASNo = 14277-97-5
| PubChem = 6426712
| SMILES = CC(\C=C\C=C(\C)/[C@H]1CN[C@@H]([C@H]1CC(=O)O)C(=O)O)C(=O)O
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>15</sub>H<sub>21</sub>NO<sub>6</sub>
| MolarMass = 311.33 g/mol
| Appearance = White powder
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| Autoignition =
| RPhrases = {{R20}} {{R21}} {{R22}}
| SPhrases = {{S36}} {{S37}}
}}
}}
'''Domoic acid''', which causes '''[[amnesic shellfish poisoning]]''' (ASP), is an [[amino acid]] associated with certain [[algal bloom]]s.<ref>[http://www.glf.dfo-mpo.gc.ca/pls/inter/dapr_view_intro?langE=en Domoic Acid and Pseudo-nitzschia References Domoic Acid and Pseudo-nitzschia References]</ref>
==Occurrence==
In [[1958]], domoic acid was originally isolated from the [[red alga]] called "doumoi" or "hanayanagi" (''Chondria armata''<ref>[http://www.usep.edu.ph/smarrdec/macrobenthic%20algae/Chondria%20armata.JPG Picture]</ref>)in [[Japan]]. "Doumoi" is used as an [[anthelmintic]] in [[Tokunoshima, Kagoshima]].{{Fact|date=November 2007}} Domoic acid is also produced by [[diatom]]s of the genus ''Pseudo-nitzschia''.<ref>[http://thalassa.gso.uri.edu/flora/genera/pseudoni.htm Pseudo-nitzschia H. Peragallo in H. & M. Peragallo 1900, emend Hasle 1993]</ref><ref>[http://www.bi.ku.dk/ioc/group1.asp Diatoms (12 species)]
</ref> Algae use domoic acid as an [[iron]] [[chelator]] to make more iron available to them.
<ref>[http://environment.newscientist.com/channel/earth/mg19826603.700-ocean-seeding-fails-the-acid-test.html "Ocean seeding fails the acid test"], [[New Scientist]] 12 June, 2008, p. 7.</ref>
Domoic acid is commercially available.
==Chemistry==
{{Expand-section|date=June 2008}}
==Toxicology==
Considerable recent research has been carried out by the [[Marine Mammal Center]] and other scientific centers on the association of [[harmful algal bloom]]s to domoic acid and to resulting [[neurological]] damage in [[marine mammal]]s of the [[Pacific Ocean]].
The chemical can [[bioaccumulation|bioaccumulate]] in [[ocean|marine]] organisms that feed on the [[phytoplankton]], such as [[shellfish]], [[anchovy|anchovies]], and [[sardine]]s. The toxin does not bioaccumulate in the classic sense because it is quickly excreted by fish and shellfish that ingest it. It only accumulates in high numbers in these plankton feeders when the diatom itself is high in number in the surrounding waters. Bioaccumulation or biomagnification typically occurs in lipid-rich tissues, which accumulate toxins over time. In classic bioaccumulation, the older and larger an organism is, the longer it has to accumulate the toxins in its fats, and therefore, the higher the concentration of toxin.
In [[mammal]]s, including [[human]]s, domoic acid acts as a [[neurotoxin]], causing short-term [[memory]] loss, [[brain]] damage and, in severe cases, [[death]]. [[Algal bloom]] 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 [[neuron]]s 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, long-term memory loss occurs.
==References==
<references/>
== External links ==
* [http://www.glf.dfo-mpo.gc.ca/pls/inter/dapr_view_intro?langE=en Domoic Acid and Pseudo-nitzschia References] at Fisheries and Oceans Canada
* [http://www.inchem.org/documents/pims/chemical/pim670.htm Domoic acid] page IPCS INCHEM
* [http://wdfw.wa.gov/fish/shelfish/razorclm/domacid.htm Domoic acid] page WDFW
{{Glutamate_receptor_ligands}}
[[Category:Neurotoxins]]
[[Category:Amino acids]]
[[Category:Pyrrolidines]]
[[ca:Àcid domoic]]
[[de:Domoinsäure]]
[[fr:Acide domoïque]]
[[ja:ドウモイ酸]]
[[pl:Kwas domoikowy]]