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D6152

Sigma-Aldrich

Domoic acid

≥90% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C15H21NO6
CAS Number:
14277-97-5
Molecular Weight:
311.33
Beilstein/REAXYS Number:
46376
MDL number:
MFCD06795841
UNSPSC Code:
12352202
PubChem Substance ID:
24894006
NACRES:
NA.77

assay

≥90% (HPLC)

form

powder

storage temp.

−20°C

SMILES string

OC([C@H](C)/C=C/C=C([C@@H]1[C@H](CC(O)=O)[C@@H](C(O)=O)NC1)/C)=O

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

InChI key

VZFRNCSOCOPNDB-AOKDLOFSSA-N

Gene Information

human ... GRIK1(2897)

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General description

Domoic acid, a heterocyclic amino acid neurotoxin is synthesized by various marine algaes. It possess some structural similarity to kainic acid.

Application

Domoic acid has been used:
  • as an excitatory neurotoxin to determine brain transcriptional response
  • to study its cytotoxic, genotoxic and immunotoxic effects on the marine mussel M. edulis
  • to study its neurobehavioral effects on mouse fetuses

Biochem/physiol Actions

Domoic acid is a potent agonist at receptors for excitatory amino acids glutamate and kainate. It has highest affinity for AMPA/kainate receptor of any kainate agonist. It can causes excessive excitation of neurons leading to depletion of energy stores.
Domoic acid serves as an antihelminthic. It is capable of binding and stimulating the kainic acid glutamate receptor in the central nervous system.
Potent glutamate receptor and kainate receptor agonist.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Glutamate Receptors (Ion Channel Family) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

hcodes

H302,H370

Hazard Classifications

Acute Tox. 4 Oral - STOT SE 1

target_organs

Central nervous system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

K2389

Kainic acid monohydrate

Kathi A Lefebvre et al.
Toxins, 11(5) (2019-05-28)
Domoic acid (DA)-producing harmful algal blooms (HABs) have been present at unprecedented geographic extent and duration in recent years causing an increase in contamination of seafood by this common environmental neurotoxin. The toxin is responsible for the neurotoxic illness, amnesic
Ananth Chandrasekaran et al.
Neurotoxicity research, 6(2), 105-117 (2004-08-25)
Domoic acid (DA), an agonist of non-N-methyl-D-aspartate (non-NMDA) receptor subtype including kainate receptor, was identified as a potent neurotoxin showing involvement in neuropathological processes like neuronal degeneration and atrophy. In the past decade evidence indicating a role for excitatory amino
Toxic motor neuronopathies and neuropathies
Handbook of Clinical Neurophysiology, 4, 437-450 (2004)
Zootoxins
Reproductive and Developmental Toxicology, 765-771 (2011)
Yu He et al.
Journal of agricultural and food chemistry, 58(22), 11525-11533 (2010-10-23)
Domoic acid (DA), a neurotoxic amino acid produced by some strains of phytoplankton, is responsible for the human toxic syndrome amnesic shellfish poisoning. This exocitotoxin results in neuronal degeneration and necrosis in specific regions of the hippocampus. Because DA accumulates
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