A mycotoxin and SERCA inhibitor
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Labeled Version(s)
31297Cyclopiazonic Acid-13C20
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Cyclopiazonic Acid

Item No. 11326

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
10-acetyl-2,6,6aR,7,11aS,11bR-hexahydro-11-hydroxy-7,7-dimethyl-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one
CAS Number
18172-33-3
Synonyms
  • CPA
  • NSC 117181
Molecular Formula
C20H20N2O3
Formula Weight
336.4
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 20 mg/mlDMSO:PBS(pH7.2) (1:1): 0.5 mg/ml
λmax
224, 281 nm
SMILES
CC1(C)N2[C@@](C(O)=C(C(C)=O)C2=O)([H])[C@@]([C@@]1([H])C3)([H])C4=CNC5=CC=CC3=C54
InChi Code
InChI=1S/C20H20N2O3/c1-9(23)14-18(24)17-16-11-8-21-13-6-4-5-10(15(11)13)7-12(16)20(2,3)22(17)19(14)25/h4-6,8,12,16-17,21,24H,7H2,1-3H3/t12-,16+,17+/m1/s1
InChi Key
SZINUGQCTHLQAZ-DQYPLSBCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Cyclopiazonic acid is a mycotoxin that has been found in Penicillium and Aspergillus and an inhibitor of sarcoplasmic/endoplasmic reticulum Ca2+-ATPase (SERCA; IC50 = 0.6 µM).1,2 In vivo, cyclopiazonic acid (11-14 mg/kg) induces ptosis, hypothermia, tremor, and cachexia, as well as induces lethality (LD50 = 13 mg/kg), in rats.3 It induces tachycardia and sedation in rabbits when administered at a dose of 10 mg/kg.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Seidler, N.W., Jona, I., Vegh, M., et al. Cyclopiazonic acid is a specific inhibitor of the Ca2+-ATPase of sarcoplasmic reticulum. The Journal of Biological Chemisty 264(30), 17816-17823 (1989).

    2. Uyama, Y., Imaizumi, Y., and Watanabe, M. Effects of cyclopiazonic acid, a novel Ca2+-ATPase inhibitor, on contractile responses in skinned ileal smooth muscle. Brit. J. Pharmacol. 106(1), 208-214 (1992).

    3. Nishie, K., Cole, R.J., and Dorner, J.W. Toxicity and neuropharmacology of cyclopiazonic acid. Food Chem. Toxicol. 23(9), 831-839 (1985).