3589-72-8

Basic information

• Product Name: 6-METHOXYHARMAN
• Synonyms: 6-METHOXYHARMAN;4-b)indole,6-methoxy-1-methyl-9h-pyrido(;6-Methoxy-1-methyl-9H-beta-carboline;6-Methoxy-1-methyl-9H-pyrido(3,4-b)indole;6-methoxyharmane;beta-Carboline, 6-methoxy-1-methyl-;coharmine;1-Methyl-6-methoxy-β-carboline
• CAS NO: 3589-72-8
• Molecular Formula: C₁₃H₁₂N₂O
• Molecular Weight: 212.25
• Mol File: 3589-72-8.mol
• Article Data: 9

Chemical Properties

• Melting Point: 275°C (dec.)
• Boiling Point: 421.4 °C at 760 mmHg
• Flash Point: 139.7 °C
• Appearance: /
• Density: 1.252 g/cm³
• Vapor Pressure: 6.42E-07mmHg at 25°C
• Refractive Index: 1.706
• Storage Temp.: 2-8°C
• PKA: 15.57±0.40(Predicted)
• CAS DataBase Reference: 6-METHOXYHARMAN(CAS DataBase Reference)
• NIST Chemistry Reference: 6-METHOXYHARMAN(3589-72-8)
• EPA Substance Registry System: 6-METHOXYHARMAN(3589-72-8)

Safety Data

• Hazardous Substances Data: 3589-72-8(Hazardous Substances Data)

Usage

Description

A further constituent of the stems and leaves of Virola cuspidata, this alkaloid is the fully unsaturated carboline corresponding to the preceding base. The ultraviolet spectrum in EtOH has absorption maxima at 232, 290, 296 and 354 mJ.1 with shoulders at 246, 257 and 285 mJ.1.

References

Cassady et al., Lloydia, 34, 161 (1971)

InChI:InChI=1/C13H12N2O/c1-8-13-10(5-6-14-8)11-7-9(16-2)3-4-12(11)15-13/h3-7,15H,1-2H3

Upstream product

• 608-07-1 2-(5-methoxyindol-3-yl)ethylamine 
• 534-15-6 1,1-dimethoxyethane 
• 89671-85-2 1-(5-methoxy-1H-indol-2-yl)ethan-1-one 
• 231295-75-3 N,5-dimethoxy-N-methyl-1H-indole-2-carboxamide 
• 61675-19-2 5-methoxy-3-(2-nitroethylenyl)-1H-indole 
• 73-31-4 5-methoxy-N-acetyl-tryptamine 
• 28052-84-8 5-methoxytryptophan 
• 29573-11-3 6-Methoxy-1-methyl-2,3,4,9-tetrahydro-1H-β-carboline-1-carboxylic acid 
• 66-83-1 5-methoxytryptamine hydrochloride 
• 1210-56-6 6-methoxy-1-methyl-1,2,3,4-tetrahydro-β-carboline 
• 3589-73-9 methoxy-6-harmalan 

Relevant articles and documents

Acid-Base and Spectral Properties of β-Carbolines. Part 2. Dehydro and Fully Aromatic β-Carbolines

The absorption and fluorescence spectra of a set of dehydro and fully aromatic β-carboline (9H-pyridoindole) derivatives have been investigated in aqueous solutions of varying acidity.Within the pH-range, cationic (nitrogen protonation) and neutral species are evidenced from both absorption and fluorescence spectra.Additional zwitterionic species can also be detected from the fluorescence spectra.In highly basic media, outside the pH-range, anionic species (pyrrolic nitrogen deprotonation) are formed.Ground state ionization constants for the differentacid-base equilibria involving these species have been determined spectrophotometrically at 25 deg C.Lowest excited singlet state pKas have been estimated from the Foerster-Weller cycle.The influence of structural variations on the spectra and on the acid-base properties of these compounds is discussed.

A new approach to 1-substituted β-carbolines and isoquinolines utilizing tributyl[(Z)-2-ethoxyvinyl]stannane as a C-3,C-4 building block

Starting from readily available indole-2-carboxylic acids, 1-substituted β-carbolines (among them the alkaloids harmane and isoharmine) are readily obtained via the corresponding 2-acylindoles, bromination at C-3, followed by a one-pot Stille cross-coupling with tributyl[(Z)-2-ethoxyvinyl]stannane, and ring closure with ammonium acetate. 1-Substituted isoquinolines are available in an analogous manner starting from 2-bromobenzoic acid.

Microwave-Assisted Synthesis of Tetrahydro-β-carbolines and β-Carbolines

A microwave-mediated Pictet-Spengler procedure utilizing 1,2-dichloroethane (DCE) and trifluoroacetic acid (TFA) was developed to provide tetrahydro-β-carboline salts in high yields. Reactions are complete in 20 minutes or less and the product precipitates from solution in high yields and purity, negating the need for liquid-liquid extraction or column chromatography. This method tolerates a wide range of functionality and can be performed on milligram to gram scales. A subsequent microwave-mediated aromatization of the synthesized tetrahydro-β-carbolines to β-carbolines was also developed utilizing catalytic Pd/C. The aromatization is complete in 60 min or less with most substrates requiring minimal purification. A microwave-assisted Pictet-Spengler procedure was developed to afford tetrahydro-β-carboline salts in high yields with no liquid-liquid extraction or chromatography required. A subsequent microwave-assisted aromatization procedure was also developed to provide β-carbolines in high yields requiring limited purification.