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D6152

Sigma-Aldrich

Domoic acid

≥90% (HPLC)

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About This Item

Formule empirique (notation de Hill) :
C15H21NO6
Numéro CAS:
14277-97-5
Poids moléculaire :
311.33
Beilstein:
46376
Numéro MDL:
MFCD06795841
Code UNSPSC :
12352202
ID de substance PubChem :
24894006
Nomenclature NACRES :
NA.77

Essai

≥90% (HPLC)

Forme

powder

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

VZFRNCSOCOPNDB-AOKDLOFSSA-N

Informations sur le gène

human ... GRIK1(2897)

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Description générale

Domoic acid, a heterocyclic amino acid neurotoxin is synthesized by various marine algaes. It possess some structural similarity to kainic acid.[1]

Application

Domoic acid has been used:
  • as an excitatory neurotoxin to determine brain transcriptional response[2]
  • to study its cytotoxic, genotoxic and immunotoxic effects on the marine mussel M. edulis[3]
  • to study its neurobehavioral effects on mouse fetuses[4]

Actions biochimiques/physiologiques

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.[5] It is capable of binding and stimulating the kainic acid glutamate receptor in the central nervous system.[6]
Potent glutamate receptor and kainate receptor agonist.

Caractéristiques et avantages

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.

Pictogrammes

Health hazardExclamation mark
GHS08,GHS07

Mention d'avertissement

Danger

Mentions de danger

H302,H370

Classification des risques

Acute Tox. 4 Oral - STOT SE 1

Organes cibles

Central nervous system

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
SLCH5087
SLCH3133
SLCD1008
SLBQ5234V
SLBN4416V

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Consulter la Bibliothèque de documents

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
Zootoxins
Reproductive and Developmental Toxicology, 765-771 (2011)
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
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
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