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Substance Name: Cyclopiazonic acid
RN: 18172-33-3
UNII: X9TLY4580Z
InChIKey: SZINUGQCTHLQAZ-DQYPLSBCSA-N

Classification Codes

  • Anti-Arrhythmia Agents
  • Cardiovascular Agents
  • Enzyme Inhibitors
  • Mutation Data
  • Reproductive Effect
  • Vasodilator Agents

Molecular Formula

  • C20-H20-N2-O3

Molecular Weight

  • 336.389
 
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Names and Synonyms

Name of Substance

  • Cyclopiazonic acid

Synonyms

  • CCRIS 4942
  • Cyclopiazonic acid
  • HSDB 7248
  • NSC 117181
  • UNII-X9TLY4580Z

Systematic Names

  • 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-, (6aalpha,11abeta,11balpha)- (8CI)(9CI)
  • 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)-rel-
  • 9H-Pyrrolo(1',2':2,3)isoindolo(4,5,6-cd)indol-9-one, 2,6,6a,7,11a,11b-hexahydro-10-acetyl-7,7-dimethyl-11-hydroxy-, (6a-alpha,11a,11b-alpha)-
  • Cyclopiazonic acid

Registry Numbers

CAS Registry Number

  • 18172-33-3

FDA UNII

  • X9TLY4580Z

System Generated Number

  • 0018172333

Structure Descriptors

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

InChIKey

SZINUGQCTHLQAZ-DQYPLSBCSA-N

Smiles

C=1(C(N2[C@H](C1O)[C@@H]1[C@H](Cc3c4c1c[nH]c4ccc3)C2(C)C)=O)C(=O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
chicken LD50 oral 12mg/kg (12mg/kg)   Poultry Science. Vol. 65(Suppl,
mouse LD50 intraperitoneal 13mg/kg (13mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: MUSCLE WEAKNESS
Food and Chemical Toxicology. Vol. 23, Pg. 831, 1985.
mouse LD50 oral 64mg/kg (64mg/kg)   Research Communications in Chemical Pathology and Pharmacology. Vol. 55, Pg. 303, 1987.
mouse LD50 oral 64mg/kg (64mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
Research Communications in Chemical Pathology and Pharmacology. Vol. 55, Pg. 303, 1987.
rabbit LDLo intraperitoneal 10mg/kg (10mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE

BRAIN AND COVERINGS: CHANGES IN SURFACE EEG
Food and Chemical Toxicology. Vol. 23, Pg. 831, 1985.
rat LD50 intraperitoneal 2mg/kg (2mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF ENDOCRINE PANCREAS

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
Toxicology and Applied Pharmacology. Vol. 18, Pg. 114, 1971.
rat LD50 oral 36mg/kg (36mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Toxicology and Applied Pharmacology. Vol. 18, Pg. 114, 1971.