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83136-88-3

83136-88-3 Structure

83136-88-3 Structure
IdentificationBack Directory
[Name]

CYCLOPIAZONIC ACID
[CAS]

83136-88-3
[Synonyms]

CPA
CYCLOPIAZONIC ACID
PENICILLIUM CYCLOPIUM
ALPHA CYCLOPIAZONIC ACID
CYCLOPIAZONIC ACID, PENICILLIUM CYCLOPIUM
(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
6H-Pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indole-9,11(2H,7H)-dione, 6a,10,11a,11b-tetrahydro-10-(1-hydroxyethylidene)-7,7-dimethyl-, (6aR,10Z,11aS,11bR)-
(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
[EINECS(EC#)]

200-585-4
[Molecular Formula]

C20H20N2O3
[MDL Number]

MFCD00167445
[MOL File]

83136-88-3.mol
[Molecular Weight]

336.38
Chemical PropertiesBack Directory
[Melting point ]

245-246 °C
[storage temp. ]

−20°C
[solubility ]

DMSO: soluble
[form ]

powder
[color ]

white to off-white
Safety DataBack Directory
[Hazard Codes ]

T
[Risk Statements ]

25
[Safety Statements ]

36/37/39-45
[RIDADR ]

UN 2811 6.1/PG 2
[WGK Germany ]

3
[RTECS ]

UY8587000
[Toxicity]

Cyclopiazonic acid is a natural contaminant of cheese, corn, and peanuts. Due to the lack of analytical methods for quantifying cyclopiazonic acid, the amount present in the food supply and the potential health risks are uncertain. Cyclopiazonic acid distributes widely in mammalian tissues, especially skeletal muscle, and produces equally diverse cytotoxicity. This toxicant shares many pharmacological properties with antipsychotic drugs including catalepsy, hypothermia, hypokinesia, ptosis, tremor, gait disturbance, sedation without loss of righting reflex, atypical convulsion, and increased barbiturate sleeping time. The mode of action of cyclopiazonic acid involves its role as an inhibitor of Ca-ATPase.
Hazard InformationBack Directory
[Uses]

Cyclopiazonic Acid is an inhibitor of endoplasmic reticulum Ca2+-ATPase.
[Definition]

ChEBI: Alpha-cyclopiazonic acid is a member of alpha-cyclopiazonic acids. It is a conjugate acid of an alpha-cyclopiazonate. It is a tautomer of a (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.
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