A neurotoxin
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Domoic Acid

Item No. 21433

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,3S,4S)-2-carboxy-4-[(1Z,3E,5R)-5-carboxy-1-methyl-1,3-hexadien-1-yl]-3-pyrrolidineacetic acid
CAS Number
14277-97-5
Synonyms
  • Domoate
  • (−)-Domoic Acid
  • L-Domoic Acid
  • NSC 288031
Molecular Formula
C15H21NO6
Formula Weight
311.3
Purity
≥98%
Formulation (Request formulation change)
A 50 µg/0.5 ml solution in water with 5% acetonitrile
Solubility(Learn about Variance in Solubility)
Methanol: 0.6 mg/mlWater: 8 mg/ml
λmax
240 nm
SMILES
C/C([C@H]1CN[C@H](C(O)=O)[C@H]1CC(O)=O)=C/C=C/[C@@H](C)C(O)=O
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    50 µg

    $255

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    Product Description

    Domoic acid is a marine-derived neurotoxin produced by N. pungens and an analog of (−)-(α)-kainic acid (Item No. 78050).1,2 Domoic acid binds to GluR5, GluR6, and GluR7 recombinant homomeric kainate receptors (Kis = 2, 6, and 37 nM, respectively), KA-1 and KA-2 kainate receptors, and the GluR4 AMPA receptor.2 It also binds to kainate and AMPA receptors in rat forebrain membranes (IC50s = 4.9 and 9.2 nM, respectively).1 In vitro, domoic acid depolarizes primary motor neurons and dorsal root fibers isolated from newborn rats at potencies of 2.2 and 34 relative to kainate, respectively.3 In vivo, domoic acid induces convulsive behavior in rats (ED50 = 0.07 nmol/animal) and induces seizures in mice with a 50% convulsive dose (CD50) value of 0.09 nmol/animal.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hampson, D.R., Huang, X.-p., Wells, J.W., et al. Interaction of domoic acid and several derivatives with kainic acid and AMPA binding sites in rat brain. Eur. J. Pharmacol. 218(1), 1-8 (1992).

    2. Hampson, D.R., and Manalo, J.L. The activation of glutamate receptors by kainic acid and domoic acid. Nat. Toxins. 6(3-4), 153-158 (1998).

    3. Ishida, M., and Shinozaki, H. Novel kainate derivatives: Potent depolarizing actions on spinal motoneurones and dorsal root fibres in newborn rats. Br. J. Pharmacol. 104(4), 873-878 (1991).

    4. Chiamulera, C., Costa, S., Valerio, E., et al. Domoic acid toxicity in rats and mice after intracerebroventricular administration: Comparison with excitatory amino acid agonists. Pharmacol. Toxicol. 70(2), 115-120 (1992).