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.[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]

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.[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.

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