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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
$118
Updated
2024/03/01
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
Alfa Aesar
Product number
J61594
Product name
Cyclopiazonic acid, 98%
Packaging
10mg
Price
$185.65
Updated
2024/03/01
Alfa Aesar
Product number
J61594
Product name
Cyclopiazonic acid, 98%
Packaging
50mg
Price
$698.65
Updated
2024/03/01
Cayman Chemical
Product number
11326
Product name
Cyclopiazonic Acid
Purity
≥95%
Packaging
1mg
Price
$25
Updated
2024/03/01
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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

CYCLOPIAZONIC ACID Preparation Products And Raw materials

Raw materials

Preparation Products

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CYCLOPIAZONIC ACID Suppliers

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18172-33-3, CYCLOPIAZONIC ACIDRelated Search:

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  • </span>-Cyclopiazonic acid / CPA
  • Cyclopiazonic acid from Penicillium grisefulvum
  • Cyclopiazonic acid (CPA)
  • Cyclopiazonic acid, FroM PenicilliuM griseofulvuM
  • (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
  • (6a-alpha,11a,11b-alpha)--10-acetyl-7-dimethyl-11-hydroxy-
  • 9h-pyrrolo(1’,2’:2,3)isoindolo(4,5,6-cd)indol-9-one,2,6,6a,7,11a,11b-hexahydro
  • (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
  • CPA
  • 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
  • 10-Acetyl-2,6,6aβ,7,11aα,11bβ-hexahydro-11-hydroxy-7,7-dimethyl-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one
  • Cyclopiazonic acid,98%
  • Cyclopiazonic Acid, 98.0+ % (HPLC)
  • Penicillium cyclopium Westling
  • Penicillium cyclopiumPCR
  • 9H-Pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one, 10-acetyl-2,6,6a,7,11a,11b-hexahydro-11-hydroxy-7,7-dimethyl-, (6aR,11aS,11bR)-
  • Cyclopiazonic acid from Penicillium grisefulvum, Ca2+-ATPase inhibitor
  • 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