D6152

Domoic acid

≥90% (HPLC)

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

Properties

• 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)

Description

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.

Safety Information

• Pictograms: GHS08,GHS07
• Signal Word: Danger
• Hazard Statements: H302,H370
• Precautionary Statements: P260 - P264 - P270 - P301 + P312 - P308 + P311 - P405
• Hazard Classifications: Acute Tox. 4 Oral - STOT SE 1
• Target Organs: Central nervous system
• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves