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D6152 Sigma-Aldrich

Domoic acid

≥90% (HPLC)

  • CAS Number 14277-97-5

  • Empirical Formula (Hill Notation) C15H21NO6

  • Molecular Weight 311.33

  •  Beilstein/REAXYS Number 46376

  •  MDL number MFCD06795841

  •  PubChem Substance ID 24894006

  •  NACRES NA.77

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Properties

Related Categories AMPA/Kainate Agonists, Algae, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology,
Quality Level   200
assay   ≥90% (HPLC)
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

Packaging

1, 5 mg in glass bottle

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.

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 & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
UX9665100
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Discover Bioactive Small Molecules for Neuroscience

The nervous system, comprised of the brain and spinal cord (central nervous system, or CNS) and network of nerves that connects the CNS to the rest of the body (peripheral nervous system, or PNS) is ...
Keywords: Bioactive small molecules, Central Nervous System, Diseases, Metabolism, Neurodegenerative Diseases, Neuroscience, Neurotransmission, Neurotransmitters

Peer-Reviewed Papers
15

References

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