115066-03-0

Basic information

• Product Name: 1,8-diethyl-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole
• CAS NO: 115066-03-0
• Molecular Formula: C₁₆H₂₁NO
• Molecular Weight: 243.344
• Mol File: 115066-03-0.mol

Chemical Properties

• Boiling Point: 390.2°C at 760 mmHg
• Flash Point: 141.7°C
• Density: 1.064g/cm³
• Vapor Pressure: 6.06E-06mmHg at 25°C
• Refractive Index: 1.577
• CAS DataBase Reference: 1,8-diethyl-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole(CAS DataBase Reference)
• NIST Chemistry Reference: 1,8-diethyl-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole(115066-03-0)
• EPA Substance Registry System: 1,8-diethyl-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole(115066-03-0)

Safety Data

• Hazardous Substances Data: 115066-03-0(Hazardous Substances Data)

Usage

Chemical class

Synthetic tetrahydroisoquinoline alkaloid

Source

Derived from the Caribbean sea squirt, Ecteinascidia turbinata

Function

DNA-binding agent

Approved for treatment

Advanced soft tissue sarcomas and ovarian cancer

Antitumor activity

Potent, through multiple mechanisms

Mechanisms of action

a. Inhibition of transcription
b. Induction of DNA damage

Potential for treatment

Other solid tumors, such as breast and prostate cancer

Unique features

a. Chemical structure
b. Mechanism of action

Therapeutic potential

Promising option for difficult-to-treat cancers

Upstream product

• 41340-25-4 etodolac 
• 67-56-1 methanol 

Relevant articles and documents

Kinetics and mechanisms of etodolac degradation in aqueous solution

The extent and mechanisms of etodolac (1; 1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]-indole-1-acetic acid) decomposition, as a function of pH and temperature, were investigated. Three main degradation products derived from 1 are identified as 7-ethyl-2-(1-methylenepropyl)-1H-indole-3-ethanol (2), the decarboxylated product of etodolac (3), and 7-ethyltryptophol (4). The main pathway for the degradation of 1 is followed by consecutive first-order kinetics: 1 → 2 ? 3 → 4. No appreciable buffer effect on the degradation of 1 is observed for any of the buffer species in the study. The rate-pH profile exhibits a specific acid catalysis at acidic (k(H)) and neutral (k'(H)) pH regions, and an inflection point at pH 4.65 corresponding to the pK(a) value. From Arrhenius plots, the activation energies (E(a)) for k(H) and k'(H) were found to be 26 and 24 kcal/mol, respectively. The small positive entropy of activation (ΔS(≠)) indicates that a unimolecular decomposition mechanism is favored for the decomposition reaction of 1.

A scaleable combined resolution and improved dosage form for etodolac with recycle of the off-isomer

An efficient resolution process using N-methyl glucamine (meglumine) which directly provides (S)-etodolac as the meglumine salt is described. This salt is also a dosage form with improved absorption characteristics. The off-isomer is efficiently racemised via the ester, prepared by mild esterification, followed by hydrolysis affording rac-etodolac suitable for recycling.