WordNet

street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

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酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/02/04 17:41:25」(JST)

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Domoic acid (DA) is a kainic acid analog 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 etc., then eat contaminated animals poisoning may result. Exposure to the biotoxin affects the brain, causing seizures, and possibly death.^[2]

History

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.^[3]

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.^[4]

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.^[5]

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.^[6]

Chemistry

Synthesis of Domoic Acid as described by Jonathan Clayden, Benjamin Read and Katherine R. Hebditch, in their article Chemistry of domoic acid, isodomoic acids, and their analogues^[7]

General

Domoic acid is a structural analog of kainic acid, proline, and endogenous excitatory neurotransmiter glutamate.^[8] Ohfune and Tomita, who wanted to investigate its absolute stereochemistry, were the first and only to synthesize domoic acid in 1982.^[9]

Biosynthesis

In 1999, using ¹³C- and ¹⁴C-labelled precursors, the biosynthesis of domoic acid in the diatom genus Pseudo-nitzschia was examined. After addition of [1,2-13C2]-acetate, NMR spectroscopy showed enrichment of every carbon in domoic acid, indicating incorporation of the carbon isotopes. This enrichment was consistent with two biosynthetic pathways. The labeling pattern determined that domoic acid can be biosynthesized by an isoprenoid intermediate in combination with a tricarboxylic acid (TCA) cycle intermediate.^[10]

Synthesis

Using intermediates 5 and 6, a Diels-Alder reaction produced a bicyclic compound (7). 7 then underwent ozonolysis to open the six-membered ring leading to selenide (8). 8 was then deselenated to form 9 (E-9 and Z-9), lastly leading to the formation of (-) domoic acid.^[11]

Mechanism of action

The effects of domoic acid have been attributed to several mechanisms, but the one of concern is through glutamate receptors. Domoic acid is an excitatory amino acid analogue of glutamate; a neurotransmitter in the brain that activates glutamate receptors. Domoic acid has a very strong affinity for these receptors, which results in excitotoxicity initiated by an integrative action on ionotropic glutamate receptors at both sides of the synapse blocking the channel from rapid desensitization. In addition there is a synergistic effect with endogenous glutamate and N-Methyl-D-aspartate receptor agonists that contribute to the excitotoxicity.

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 normal, the uncontrolled increase of calcium causes the cells to degenerate. Because the hippocampus may be severely damaged, short-term memory loss occurs. It may also cause kidney damage – even at levels considered safe for human consumption, a new study in mice has revealed. The kidney is affected at a hundred times lower than the concentration allowed under FDA regulations.^[12]^[13]

Symptoms

Humans	Other Animals
vomiting	head weaving
nausea	seizures
diarrhea and abdominal cramps within 24 hours of ingestion	bulging eyes
headache	mucus from the mouth
dizziness	disorientation
confusion, disorientation	death
loss of short-term memory
motor weakness
seizures
profuse respiratory secretions
cardiac arrhythmias
coma and possible death

^[14]

Toxicology

Domoic acid producing algal blooms are associated with the phenomenon of amnesic shellfish poisoning (ASP). Domoic acid can bioaccumulate in marine organisms such as shellfish, anchovies, and sardines that feed on the phytoplankton known to produce this toxin. It can accumulate in high concentrations in the tissues of these plankton feeders when the toxic phytoplankton are high in concentration in the surrounding waters. Domoic acid is a neurotoxin that inhibits neurochemical processes, causing short-term memory loss, brain damage, and, in severe cases, death in humans. In marine mammals, domoic acid typically causes seizures and tremors.

Studies have shown that there are no symptomatic effects in humans at levels of 0.5 mg/kg of body weight. In the 1987 domoic acid poisoning on Prince Edward Island concentrations ranging from 0.31–1.28 mg/kg of muscle tissue were noted in people that became ill (three of whom died). Dangerous levels of domoic acid have been calculated based on cases such as the one on Prince Edward island. The exact LD₅₀ for humans is unknown; for mice the LD₅₀ is 3.6 mg/kg.^[15]

New research has found that domoic acid is a heat-resistant and very stable toxin, which can damage kidneys at concentrations that are 100 times lower than what causes neurological effects.^[16]

Diagnosis and prevention

In order to be diagnosed and treated if poisoned, domoic acid must first be detected. Methods such as ELISA or probe development with polymerase chain reaction (PCR) may be used to detect the toxin or the organism producing this toxin.^[17]

There is no known antidote available for domoic acid. Therefore, if poisoning occurs, it is advised to go quickly to a hospital. Cooking or freezing affected fish or shellfish tissue that are contaminated with domoic acid does not lessen the toxicity.^[18]

As a public health concern, the concentration of domoic acid in shellfish and shellfish parts at point of sale should not exceed the current permissible limit of 20 mg/kg tissue. In addition during processing shellfish, it is important to pay attention to environmental condition factors.^[19]

Pop culture

On August 18, 1961, in Capitola and Santa Cruz, California there was an invasion of what people described as chaotic seabirds. These birds were believed to be under the influence of domoic acid, and it inspired a scene in Alfred Hitchcock’s feature film The Birds (film).^[20]

In addition domoic acid was used to poison a witness in the Elementary (TV series), episode The Red Team.

Domoic acid overtakes Camp Kikiwaka causing the campers to develop bizarrely altered personalities in the TV Series Bunk'd Season 2 Episode 10

References

^ Clayden, Jonathan; Read, Benjamin; Hebditch, Katherine. "Chemistry of domoic acid, isodomoic acids, and their analogues" (PDF). Retrieved 2 April 2015.
^ "Domoic Acid Toxicity". The Marine Mammal Center. Retrieved 2 April 2015.
^ "Domoic Acid Poisoning". Northwest Fisheries science center. Retrieved 17 April 2015.
^ "DOMOIC ACID - A major concern to washington state's shellfish lovers". Washington Department of Fish and wildlife. Retrieved 12 April 2015.
^ Gilbert, Steven. "Domoic Acid". Toxipedia. Retrieved 15 April 2015.
^ "Possibly drunk pelican hits windshield". NBC news. Retrieved 12 April 2015.
^ Clayden, Jonathan; Read, Benjamin; Hebditch, Katherine. "Chemistry of domoic acid, isodomoic acids, and their analogues" (PDF). Retrieved 2 April 2015.
^ http://onlinelibrary.wiley.com/doi/10.1002/ana.410370125/full
^ Clayden, Jonathan; Read, Benjamin; Hebditch, Katherine. "Chemistry of domoic acid, isodomoic acids, and their analogues" (PDF). Retrieved 2 April 2015.
^ Ramsey; Douglas; Walter; Wright (1999). "Biosynthesis of domoic acid by the diatom Pseudo-nitzschia multiseries". Natural Toxins. 6 (3–4): 137–46. doi:10.1002/(sici)1522-7189(199805/08)6:3/4<137::aid-nt28>3.0.co;2-l. PMID 10223629.
^ Clayden, Jonathan; Read, Benjamin; Hebditch, Katherine. "Chemistry of domoic acid, isodomoic acids, and their analogues" (PDF). Retrieved 2 April 2015.
^ Pulido, Olga (2008). "Domoic Acid Toxicologic Pathology: A Review". Mar Drugs. 6 (2): 180–219. doi:10.3390/md20080010. PMC 2525487. PMID 18728725.
^ Smith, Torrey. "Toxin in seafood causes kidney damage in mice at levels considered safe for consumption". avante medical center.
^ Gilbert, Steven. "Domoic Acid". Toxipedia. Retrieved 2 April 2015.
^ Gilbert, Steven. "Domoic Acid". Toxipedia.
^ Smith, Torrey. "Toxin in seafood causes kidney damage in mice at levels considered safe for consumption". avante medical center.
^ "Detection and Analysis of Marine Biotoxins". Northwest fisheries science center.
^ "Domoic Acid - A Major Concern to Washington State's Shellfish Lovers". washington department of fish and wildlife.
^ Kumar, K. Prem; Kumar, Sreeletha Prem; Nair, G. Achuthan (2009). "Risk assessment of the amnesic shellfish poison, domoic acid, on animals and humans". Journal of Environmental Biology. 30 (3): 319–25. PMID 20120452.
^ Bargu, Sibel; Silver, Mary W.; Ohman, Mark D.; Benitez-Nelson, Claudia R.; Garrison, David L. (2011). "Mystery behind Hitchcock's birds". Nature Geoscience. 5 (1): 2–3. Bibcode:2012NatGe...5....2B. doi:10.1038/ngeo1360.

External links

"Domoic Acid and Pseudo-nitzschia References". Fisheries and Oceans Canada. Archived from the original on 2013-12-04.
"Amnesic Shellfish Poisoning, Domoic Acid, and Pseudo-nitzschia". International Society for the Study of Harmful Algae ISSHA.
"Domoic acid". IPCS INCHEM.
"Domoic Acid - A Major Concern to Washington State's Shellfish Lovers". Washington Department of Fish and Wildlife.
"Domoic Acid Toxicity".

UpToDate Contents

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English Journal

Neurobehavioral assessment of mice following repeated oral exposures to domoic acid during prenatal development.

Shiotani M1, Cole TB2, Hong S3, Park JJY3, Griffith WC1, Burbacher TM3, Workman T1, Costa LG4, Faustman EM5.
Neurotoxicology and teratology.Neurotoxicol Teratol.2017 Sep 13;64:8-19. doi: 10.1016/j.ntt.2017.09.002. [Epub ahead of print]
PMID 28916171

Post-Mortem DTI Reveals Altered Hippocampal Connectivity in Wild Sea Lions Diagnosed with Chronic Toxicosis from Algal Exposure.

Cook PF1,2, Berns GS2, Colegrove K3, Johnson S4, Gulland F4.
The Journal of comparative neurology.J Comp Neurol.2017 Sep 5. doi: 10.1002/cne.24317. [Epub ahead of print]
PMID 28875534

Occurrence of marine algal toxins in oyster and phytoplankton samples in Daya Bay, South China Sea.

Jiang T1, Liu L2, Li Y3, Zhang J4, Tan Z5, Wu H5, Jiang T6, Lu S7.
Chemosphere.Chemosphere.2017 Sep;183:80-88. doi: 10.1016/j.chemosphere.2017.05.067. Epub 2017 May 12.
PMID 28535464

Japanese Journal

Pseudo-nitzschia fukuyoi (Bacillariophyceae), a domoic acid-producing species from Nha Phu Bay, Khanh Hoa Province, Vietnam

Fisheries science 81(3), 533-539, 2015-05
NAID 40020473200

Prenatal exposure effects of repeated oral dose of domoic acid on neurobehavior in mice

日本毒性学会学術年会 42.1(0), P-181, 2015
NAID 130005483443

Production of domoic acid by laboratory culture of the red alga Chondria armata

Toxicon 92, 1-5, 2014-12-15
NAID 120005511023

Related Pictures

★リンクテーブル★

リンク元	「ドーモイ酸」「domoate」

「ドーモイ酸」

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
3D model (Jmol)	Interactive image
ChEBI	CHEBI:34727
ChEMBL	ChEMBL420720
ChemSpider	4445428
ECHA InfoCard	100.159.099
IUPHAR/BPS	4181
PubChem	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 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	311.3303 g/mol
Density	1.273 g/cm3
Boiling point	at 760 mmHg 607.2 °C (1,125.0 °F; 880.4 K)
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 (610 °F; 594 K)
	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

　　[★]

英: domoate, domoic acid
関: カイニン酸受容体刺激薬、カイニン酸

カイニン酸受容体刺激薬

「domoate」

　　[★] ドーモイ酸, domoic acid

[1] Clayden, Jonathan; Read, Benjamin; Hebditch, Katherine. "Chemistry of domoic acid, isodomoic acids, and their analogues" (PDF). Retrieved 2 April 2015.

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

[3] "Domoic Acid Poisoning". Northwest Fisheries science center. Retrieved 17 April 2015.

[4] "DOMOIC ACID - A major concern to washington state's shellfish lovers". Washington Department of Fish and wildlife. Retrieved 12 April 2015.

[5] Gilbert, Steven. "Domoic Acid". Toxipedia. Retrieved 15 April 2015.

[6] "Possibly drunk pelican hits windshield". NBC news. Retrieved 12 April 2015.

[7] Clayden, Jonathan; Read, Benjamin; Hebditch, Katherine. "Chemistry of domoic acid, isodomoic acids, and their analogues" (PDF). Retrieved 2 April 2015.

[8] ttp://onlinelibrary.wiley.com/doi/10.1002/ana.410370125/full

[9] Clayden, Jonathan; Read, Benjamin; Hebditch, Katherine. "Chemistry of domoic acid, isodomoic acids, and their analogues" (PDF). Retrieved 2 April 2015.

[10] Ramsey; Douglas; Walter; Wright (1999). "Biosynthesis of domoic acid by the diatom Pseudo-nitzschia multiseries". Natural Toxins. 6 (3–4): 137–46. doi:10.1002/(sici)1522-7189(199805/08)6:3/4<137::aid-nt28>3.0.co;2-l. PMID 10223629.

[11] Clayden, Jonathan; Read, Benjamin; Hebditch, Katherine. "Chemistry of domoic acid, isodomoic acids, and their analogues" (PDF). Retrieved 2 April 2015.

[12] Pulido, Olga (2008). "Domoic Acid Toxicologic Pathology: A Review". Mar Drugs. 6 (2): 180–219. doi:10.3390/md20080010. PMC 2525487. PMID 18728725.

[13] Smith, Torrey. "Toxin in seafood causes kidney damage in mice at levels considered safe for consumption". avante medical center.

[14] Gilbert, Steven. "Domoic Acid". Toxipedia. Retrieved 2 April 2015.

[15] Gilbert, Steven. "Domoic Acid". Toxipedia.

[16] Smith, Torrey. "Toxin in seafood causes kidney damage in mice at levels considered safe for consumption". avante medical center.

[17] "Detection and Analysis of Marine Biotoxins". Northwest fisheries science center.

[18] "Domoic Acid - A Major Concern to Washington State's Shellfish Lovers". washington department of fish and wildlife.

[19] Kumar, K. Prem; Kumar, Sreeletha Prem; Nair, G. Achuthan (2009). "Risk assessment of the amnesic shellfish poison, domoic acid, on animals and humans". Journal of Environmental Biology. 30 (3): 319–25. PMID 20120452.

[20] Bargu, Sibel; Silver, Mary W.; Ohman, Mark D.; Benitez-Nelson, Claudia R.; Garrison, David L. (2011). "Mystery behind Hitchcock's birds". Nature Geoscience. 5 (1): 2–3. Bibcode:2012NatGe...5....2B. doi:10.1038/ngeo1360.

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domoic acid