Skip to Content
Merck
CN

D6152

Domoic acid

≥90% (HPLC)

Sign In to View Organizational & Contract Pricing.

Select a Size

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

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

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)

Looking for similar products? Visit Product Comparison Guide

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SLCH5087
SLCH3133
SLCD1008
SLBQ5234V
SLBN4416V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Zootoxins
Reproductive and Developmental Toxicology, 765-771 (2011)
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
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
Toxic motor neuronopathies and neuropathies
Handbook of Clinical Neurophysiology, 4, 437-450 (2004)
Olga M Pulido
Marine drugs, 6(2), 180-219 (2008-08-30)
Domoic acid was identified as the toxin responsible for an outbreak of human poisoning that occurred in Canada in 1987 following consumption of contaminated blue mussels [Mytilus edulis]. The poisoning was characterized by a constellation of clinical symptoms and signs.
View All Related Papers

Articles

DISCOVER Bioactive Small Molecules for Neuroscience

DISCOVER Bioactive Small Molecules for Neuroscience

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service