40959-16-8

Basic information

• Product Name: 7-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-beta-carboline hydrochloride (1:1)
• CAS NO: 40959-16-8
• Molecular Formula: C₁₃H₁₆N₂O*ClH
• Molecular Weight: 252.7399
• Mol File: 40959-16-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 399.2°C at 760 mmHg
• Flash Point: 195.2°C
• Vapor Pressure: 1.4E-06mmHg at 25°C
• CAS DataBase Reference: 7-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-beta-carboline hydrochloride (1:1)(CAS DataBase Reference)
• NIST Chemistry Reference: 7-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-beta-carboline hydrochloride (1:1)(40959-16-8)
• EPA Substance Registry System: 7-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-beta-carboline hydrochloride (1:1)(40959-16-8)

Safety Data

• Hazardous Substances Data: 40959-16-8(Hazardous Substances Data)

Usage

General Description

7-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-beta-carboline hydrochloride (1:1) is a chemical compound belonging to the beta-carboline class of substances, known for their various pharmacological properties. They are often derived from plants and can impact the central nervous system. The “1:1” in its name refers to the ratio of the chemical to hydrochloride in the compound. Its precise effects and uses may vary, but it is usually studied and used in the context of pharmacology and may undergo further derivatization to form specific kinds of drugs or therapeutic agents. As with many substances of its kind, it requires careful handling and specific storage conditions to maintain its stability and efficacy.

Synthetic route

1,1-dimethoxyethane (534-15-6) + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → 7-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride (40959-16-8)

Conditions	Yield
Stage #1: 1,1-dimethoxyethane; 2-(6-methoxy-1H-indol-3-yl)ethanamine With trifluoroacetic acid In 1,2-dichloro-ethane at 110℃; for 0.05h; Pictet-Spengler Synthesis; Sealed tube; Microwave irradiation; Stage #2: With hydrogenchloride In ethyl acetate at 20℃;	98%

7-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride (40959-16-8) → harmine (442-51-3)

Conditions	Yield
With 5 mol% Pd/C; lithium carbonate In ethanol at 150℃; for 0.166667h; Sealed tube; Microwave irradiation;	99%

Upstream product

• 534-15-6 1,1-dimethoxyethane 
• 3610-36-4 2-(6-methoxy-1H-indol-3-yl)ethanamine 

Downstream Products

• 442-51-3 harmine 

Relevant articles and documents

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.