CYCLOPIAZONIC ACID

Product Name: CYCLOPIAZONIC ACID
CAS No.: 18172-33-3
Chemical Name: CYCLOPIAZONIC ACID
Synonyms: CPA;CYCLOPIAZONIC ACID;gamma-linolenoyl-CoA;PENICILLIUM CYCLOPIUM;Cyclopiazonic acid,98%;Cyclopiazonic acid (CPA);ALPHA CYCLOPIAZONIC ACID;Penicillium cyclopiumPCR;CYCLOPIAZONICACID,BIOTECHGRADE;Penicillium cyclopium Westling
CBNumber: CB9207176
Molecular Formula: C20H20N2O3
Formula Weight: 336.38
MOL File: 18172-33-3.mol

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CYCLOPIAZONIC ACID Property

Melting point:: 245-246°C
Boiling point:: 472.86°C (rough estimate)
Density: 1.2171 (rough estimate)
refractive index: 1.5700 (estimate)
storage temp.: -20°C
solubility: DMSO: soluble
form: powder
pka: 4.50±1.00(Predicted)
color: white to off-white
Water Solubility: Soluble in DMSO (100 mM), ethanol (5 mM), DMF (~20 mg/ml), and 1:1 DMSO:PBS(pH 7.2) (0.5 mg/ml). Insoluble in water.
EPA Substance Registry System: Cyclopiazonic acid (18172-33-3)

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Safety

Hazard Codes: T
Risk Statements: 25
Safety Statements: 36/37/39-45
RIDADR: UN 2811 6.1/PG 2
WGK Germany: 3
RTECS: UY8587000
HazardClass: 6.1(a)
PackingGroup: II
HS Code: 29337900
Hazardous Substances Data: 18172-33-3(Hazardous Substances Data)
Toxicity: chicken,LD50,oral,12mg/kg (12mg/kg),Poultry Science. Vol. 65(Suppl,

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H300Fatal if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: C1530
Product name: Cyclopiazonic acid from Penicillium cyclopium
Purity: ≥98% (HPLC), powder
Packaging: 5mg
Price: $114.95
Updated: 2025/07/31

Sigma-Aldrich

Product number: 239805
Product name: Cyclopiazonic Acid,
Purity: A cell-permeable, reversible inhibitor of sarcoplasmic reticulum Ca
Packaging: 5mg
Price: $96.4
Updated: 2023/01/07

Cayman Chemical

Product number: 11326
Product name: Cyclopiazonic Acid
Purity: ≥95%
Packaging: 1mg
Price: $25
Updated: 2024/03/01

Cayman Chemical

Product number: 11326
Product name: Cyclopiazonic Acid
Purity: ≥95%
Packaging: 5mg
Price: $71
Updated: 2024/03/01

Sigma-Aldrich

Product number: C1530
Product name: Cyclopiazonic acid from Penicillium cyclopium
Purity: ≥98% (HPLC), powder
Packaging: 10mg
Price: $212
Updated: 2025/07/31

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CYCLOPIAZONIC ACID Chemical Properties,Usage,Production

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). 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. It induces tachycardia and sedation in rabbits when administered at a dose of 10 mg/kg.

Chemical Properties

off-white powder or crystals

Uses

Cyclopiazonic acid is a tremorigenic indole produced by several species of Aspergillus and Penicillium. Cyclopiazonic acid is a highly specific inhibitor of calcium ATPase of sarcoplasmic reticulum, altering calcium homeostasis and ATP-dependent calcium transport and resulting in the release of intracellular stored Ca2+ without increasing IP3.

Uses

The use of Cyclopiazonic acid on Langendorff-perfused murine hearts displayed anti-arrhythmic effects. Also, administration of cyclopiazonic acid on rat soleus muscle showed a decrease in hormone sensitive lipase activity and triacylglycerol hydrolysis. It is also used as an inhibitor of endoplasmic reticulum Ca2+-ATPase.

Uses

Cyclopiazonic acid from?Penicillium cyclopium has been used:

as a standard in aflatoxin detection and quantification by thin layer chromatography (TLC)
as a component in Ca²⁺-free DMEM/10% fetal bovine serum (FBS)
as a reversible inhibitor of the sarco/endoplasmic reticulum Ca²⁺-ATPase (SERCA) to examine the role of luminal calcium in endoplasmic recticulum (ER)-to-Golgi trafficking
as an endoplasmic reticulum Ca²⁺-ATPase blocker, to treat neurons and also to study the role of the endoplasmic reticulum (ER) in releasing and sustaining Ca²⁺?during Ca²⁺-induced Ca²⁺ release (CICR) to inhibit SERCA

General Description

Cyclopiazonic acid (CPA), a tetramic acid is synthesized by various Aspergillus and Penicillium species.

Biological Activity

Cell-permeable, reversible inhibitor of sarcoplasmic reticulum Ca 2+ -ATPase.

Biochem/physiol Actions

Inhibits the sarcoplasmic reticulum Ca2+-pump.

storage

-20°C

References

[1] N W SEIDLER. Cyclopiazonic acid is a specific inhibitor of the Ca2+-ATPase of sarcoplasmic reticulum.[J]. The Journal of Biological Chemistry, 1989, 264 30: 17816-17823.
[2] Y UYAMA M W Y Imaizumi. Effects of cyclopiazonic acid, a novel Ca(2+)-ATPase inhibitor, on contractile responses in skinned ileal smooth muscle.[J]. British Journal of Pharmacology, 1992, 106 1: 208-214. DOI: 10.1111/j.1476-5381.1992.tb14316.x
[3] K. NISHIE J. W D R J Cole. Toxicity and neuropharmacology of cyclopiazonic acid[J]. Food and Chemical Toxicology, 1985, 23 9: Pages 831-839. DOI: 10.1016/0278-6915(85)90284-4

CYCLOPIAZONIC ACID Preparation Products And Raw materials

Raw materials

Preparation Products

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CYCLOPIAZONIC ACID Suppliers

Australia 1 Belgium 1 China 98 Germany 6 India 1 Switzerland 2 United Kingdom 8 United States 17 Global 134

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18172-33-3, CYCLOPIAZONIC ACIDRelated Search:

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Cyclopiazonic acid from Penicillium grisefulvum

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(6aR,11aS,11bR)-10-acetyl-11-hydroxy-7,7-dimethyl-2,6,6a,7,11a,11b-hexahydro-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one

Cyclopiazonic acid, 98%, from Penicillium griseofulvum

Cyclopiazonic Acid, Penicillium cyclopium - CAS 18172-33-3 - Calbiochem

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(6AA, 10Z, 11AB, 11BA)-6A,7,11A,11B-TETRAHYDRO-10-(1-HYDROXYETHYLIDENE)-7,7- DIMETHYL-6H-PYRROLO [1',2':2,3]ISOINDOLO [4,5,6-CD]INDOLE-9,11 (2H,10H)-DIONE

(6AR,11AS,11BR)-REL-10-ACETYL-2,6,6A,7,11A,11B-HEXAHYDRO-7,7-DIMETHYL-9H-PYRROLO[1',2':2,3]ISOINDOLO[4,5,6-CD]INDOL-9-ONE

ALPHA CYCLOPIAZONIC ACID

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CYCLOPIAZONIC ACID

CYCLOPIAZONIC ACID, PENICILLIUM CYCLOPIUM

CYCLOPIAZONIC ACID FROM PENICILLIUMCYCLO PIUM MINIM

9H-Pyrrolo1,2:2,3isoindolo4,5,6-cdindol-9-one, 10-acetyl-2,6,6a,7,11a,11b-hexahydro-11-hydroxy-7,7-dimethyl-, (6aR,11aS,11bR)-rel-

CYCLOPIAZONICACID,BIOTECHGRADE

[5-(6-aminopurin-9-yl)-4-hydroxy-2-[[hydroxy-[hydroxy-[3-hydroxy-2,2-dimethyl-3-[2-(2-octadeca-6,9,12-trienoylsulfanylethylcarbamoyl)ethylcarbamoyl]propoxy]phosphoryl]oxy-phosphoryl]oxymethyl]oxolan-3-yl]oxyphosphonic acid

gamma-linolenoyl-CoA

Cyclopiazonic acid from Penicillium cyclopium

PENICILLIUM CYCLOPIUM

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Cyclopiazonic acid,98%

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18172-33-3

181172-33-3

C20H20N2O3

C39H64N7O17P3S

Intracellular Calcium Regulators

Intracellular Calcium Signaling

Cell Biology

Cell Signaling and Neuroscience

BioChemical

antibiotic

Signalling

Calcium signaling