CYCLOPIAZONIC ACID

Description

CYCLOPIAZONIC ACID · CAS 18172-33-3 · C20H20N2O3. UNII X9TLY4580Z. Melting Point: 245-246 °C.

Identification

CAS Registry Number	18172-33-3
PubChem CID	54682463
Molecular formula	C20H20N2O3
IUPAC name	(2R,3S,9R)-5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.02,9.03,7.015,18]octadeca-1(17),4,11(18),12,14-pentaen-6-one
UNII (FDA)	X9TLY4580Z

Computed Descriptors

Molecular Weight	336.4
XLogP3	2.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	1
Exact Mass	336.14739250
Monoisotopic Mass	336.14739250
Topological Polar Surface Area	73.4
Heavy Atom Count	25
Formal Charge	0

Physical & Chemical Properties

Melting Point	245-246 °C

Physical description & handling notes

• Solid; [HSDB]
• A solid
• When heated to decomposition it emits toxic fumes of /nitrogen oxides/
• 174 Ų [M-H]- [CCS Type: TW; Method: calibrated with polyalanine]

GHS Hazard Classification

Reported hazard statements	H300 (100%)

Documented Uses

• Suspected cause of kodua poisoning in humans from eating kodo millet seed in India; Mycotoxin produced by Aspergillus and Penicillium; [HSDB] Produced by Penicillium and Aspergillus species in moldy millet or ground nut meal; Also produced by some strains of Penicillium camemberti used to make gourmet cheese; [Reference #1]
• Cyclopiazonic acid (CPA) is suspected of causing "kodua poisoning" in humans who consumed kodo millet seed in India.
• ...More than one mold can produce the same mycotoxin (e.g., both Aspergillus and Penicillium may produce the mycotoxin cyclopiazonic acid).
• Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade.
• Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
• Drugs used to cause dilation of the blood vessels.

Synonyms

18172-33-3; NSC 117181; cyclopyazonic acid; NSC-117181; RefChem:919428; CHEBI:38615; DTXCID701031035; Cyclopiazonic Acid; DTXSID00891798; X9TLY4580Z; cyclopiazonic-acid; 2o9j; 2oa0; BSPBio_001303; GTPL5350; orb1218590

Frequently Asked Questions

What are the CAS number and molecular formula of CYCLOPIAZONIC ACID?

CAS 18172-33-3; molecular formula C20H20N2O3; molecular weight — g/mol.

What other names is CYCLOPIAZONIC ACID known by?

18172-33-3, NSC 117181, cyclopyazonic acid, NSC-117181, RefChem:919428, CHEBI:38615.

Is CYCLOPIAZONIC ACID classified as hazardous?

Hazard statements reported: H300.

What are the key physical properties of CYCLOPIAZONIC ACID?

Melting Point: 245-246 °C.

Facts on this page are taken from PubChem (US National Library of Medicine) and Wikidata. Grade-specific data — assay, moisture, particle size, packaging, shelf life — is issued per batch on the COA and is not published here.