83136-88-3

Basic information

• Product Name: CYCLOPIAZONIC ACID
• Synonyms: ALPHA CYCLOPIAZONIC ACID;(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;(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;CPA;CYCLOPIAZONIC ACID;CYCLOPIAZONIC ACID, PENICILLIUM CYCLOPIUM;PENICILLIUM CYCLOPIUM
• CAS NO: 83136-88-3
• Molecular Formula: C20H20N2O3
• Molecular Weight: 336.38
• EINECS: 200-585-4
• Mol File: 83136-88-3.mol

Chemical Properties

• Melting Point: 245-246 °C
• Appearance: white to off-white/powder
• Storage Temp.: −20°C
• Solubility: DMSO: soluble
• CAS DataBase Reference: CYCLOPIAZONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLOPIAZONIC ACID(83136-88-3)
• EPA Substance Registry System: CYCLOPIAZONIC ACID(83136-88-3)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 36/37/39-45
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 3
• RTECS: UY8587000
• Hazardous Substances Data: 83136-88-3(Hazardous Substances Data)

Usage

Uses

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

Upstream product

• 92471-22-2 iso-α-cyclopiazonic acid 
• 674-82-8 4-methyleneoxetan-2-one 
• 98664-89-2 (6aRS,9aSR,9SR)-ethyl 6,6a,7,8,9,9a-hexahydro-7,7-dimethylisoindolo[4,5,6-cd]indole-9-carboxylate 
• 79681-04-2 1-[(4-methyl-phenyl)-sulfonyl]-1H-indol-4-carboxaldehyde 
• 92420-71-8 4-[2-(2-Methyl-[1,3]dioxolan-2-yl)-ethyl]-1H-indole 
• 98664-96-1 4-[2-(2-Methyl-[1,3]dioxolan-2-yl)-ethyl]-1H-indole-3-carbaldehyde 
• 92420-72-9 (Z)-2-Acetylamino-3-{4-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-1H-indol-3-yl}-acrylic acid ethyl ester 
• 92420-74-1 (3R,4R)-4-Acetyl-3-(acetylamino-ethoxycarbonyl-methyl)-4-phenylsulfanyl-4,5-dihydro-3H-benzo[cd]indole-1-carboxylic acid ethyl ester 
• 92420-76-3 (6aS,9R,9aS)-8-Acetyl-7-methyl-7-phenylsulfanyl-7,8,9,9a-tetrahydro-6H,6aH-isoindolo[4,5,6-cd]indole-2,9-dicarboxylic acid diethyl ester 
• 92420-75-2 (3R,4R)-4-Acetyl-3-(acetylamino-ethoxycarbonyl-methyl)-4,5-dihydro-3H-benzo[cd]indole-1-carboxylic acid ethyl ester 
• 92420-77-4 (6aS,9R,9aS)-8-Acetyl-7,7-dimethyl-7,8,9,9a-tetrahydro-6H,6aH-isoindolo[4,5,6-cd]indole-2,9-dicarboxylic acid diethyl ester 
• 92420-73-0 3-((Z)-2-Acetylamino-2-ethoxycarbonyl-vinyl)-4-(3-oxo-2-phenylsulfanyl-butyl)-indole-1-carboxylic acid ethyl ester 
• 92420-78-5 (6aR,9S,9aR)-7,7-Dimethyl-8-(3-oxo-butyryl)-7,8,9,9a-tetrahydro-6H,6aH-isoindolo[4,5,6-cd]indole-2,9-dicarboxylic acid diethyl ester 
• 2829-38-1 1,4-dioxo-1,3-butadiene 

Downstream Products

• 31008-94-3 C₂₀H₂₁N₃O₂ 

Relevant articles and documents

A total synthesis of (±)-α-cyclopiazonic acid using a cationic cascade

The indolic terpene alkaloid α-cyclopiazonic acid 1 has been prepared in 11 steps from indole-4-methanol 6; the key step is a carbocationic cascade, terminated by a 4-nitrosulfonamide group and initiated by benzylic carbocation formation directly from the

TOTAL SYNTHESIS OF (+/-)-α-CYCLOPIAZONIC ACID

(+/-)-α-Cyclopiazonic acid (2) was synthesized from 1-methoxycarbonyl-4-(3-oxo-1-butyl)indole (1) by way of 17, 18, and 19 using a reaction of MeLi with a pyrroline derivative 33 in the presence of BF3*Et2O.