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Merck
CN

D6152

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
UNSPSC Code:
12352202
NACRES:
NA.77
PubChem Substance ID:
24894006
MDL number:
MFCD06795841
Beilstein/REAXYS Number:
46376
Assay:
≥90% (HPLC)
Form:
powder

Key Documents

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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

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 key

VZFRNCSOCOPNDB-AOKDLOFSSA-N

assay

≥90% (HPLC)

form

powder

storage temp.

−20°C

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.

signalword

Danger

pictograms

Health hazardExclamation mark
GHS08,GHS07

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

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SLCH5087
SLCH3133
SLCD1008
SLBQ5234V
SLBN4416V

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Seafood Neurotoxins I: Shellfish Poisoning and the Nervous System
Clinical Neurotoxicology, 441-447 (2009)
Emmanuel Van Acker et al.
Marine drugs, 18(1) (2020-01-16)
Respiratory exposure to marine phycotoxins is of increasing concern. Inhalation of sea spray aerosols (SSAs), during harmful Kareniabrevis and Ostreopsisovata blooms induces respiratory distress among others. The biogenics hypothesis, however, suggests that regular airborne exposure to natural products is health
E Selander et al.
Science advances, 5(2), eaat5096-eaat5096 (2019-02-26)
Fear of predation may influence food webs more than actual predation. However, the mechanisms and magnitude of nonconsumptive predator effects are largely unknown in unicellular-dominated food webs such as marine plankton. We report a general mechanism of chemically induced predator
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
M Andjelkovic et al.
Environment international, 49, 115-119 (2012-09-27)
A main known culprit causing amnesic shellfish poisoning in humans is domoic acid (DA). The toxin appearance in sea waters (by counting the toxin producing algae) and consequently in shellfish is closely monitored to prevent acute intoxications with gastrointestinal symptoms
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