3166-78-7

Basic information

• Product Name: 2-(2,4,5-trimethoxyphenyl)ethanamine
• Synonyms: Benzeneethanamine,2,4,5-trimethoxy-, hydrochloride (9CI); Phenethylamine, 2,4,5-trimethoxy-, hydrochloride(7CI,8CI); 2,4,5-Trimethoxyphenylethylamine hydrochloride
• CAS NO: 3166-78-7
• Molecular Formula: C₁₁H₁₇NO₃*ClH
• Molecular Weight: 0
• Mol File: 3166-78-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 320.5°Cat760mmHg
• Flash Point: 152.7°C
• Appearance: /
• Density: 1.067g/cm³
• CAS DataBase Reference: 2-(2,4,5-trimethoxyphenyl)ethanamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2,4,5-trimethoxyphenyl)ethanamine(3166-78-7)
• EPA Substance Registry System: 2-(2,4,5-trimethoxyphenyl)ethanamine(3166-78-7)

Safety Data

• Hazardous Substances Data: 3166-78-7(Hazardous Substances Data)

Usage

General Description

2-(2,4,5-trimethoxyphenyl)ethanamine, also known as TMA-2, is a psychedelic drug and entactogen of the phenethylamine and amphetamine chemical classes. It is a potent agonist at serotonin receptors and has been used in scientific research to study the effects of psychedelic compounds on the brain. TMA-2 is a close structural analog of mescaline, a naturally occurring psychedelic compound found in certain cacti. It is known for its hallucinogenic and euphoric effects, and is considered to be a Schedule I controlled substance in the United States due to its potential for abuse and lack of accepted medical use.

Upstream product

• 4460-86-0 asaraldehyde 
• 125438-24-6 2,4,5-trimethoxybenzaldehyde O-(trimethylsilyl)cyanohydrin 

Downstream Products

• 14430-23-0 5,6-dimethoxyindole 
• 106103-12-2 2,2,2-Trifluoro-N-[2-(2,4,5-trimethoxy-phenyl)-ethyl]-acetamide 
• 490-64-2 asaronic acid 

Relevant articles and documents

Preparation of Quinone Imine Ketals via Intramolecular Condensation of Amino-Substituted Quinone Monoketals. Anodic Oxidation Chemistry of Trifluoracetamide Derivatives of 1,4-Dimethoxybenzenes and 4-Methoxyphenols

Two routes have been developed to the previously unknown quinone imine ketal moiety.One involves a sequence of anodic oxidation of the N-trifluoroacetamide of a 2-(2,5-dimethoxyphenyl)ethylamine or 3-(2,5-dimethoxyphenyl)propylamine derivative to form the respective quinone bisketal followed by basic hydrolysis of the trifluoroacetamide linkage, acidic hydrolysis of the quinone bisketal to a quinone monoketal, and intramolecular condensation to form the quinone imine ketal.This method reuires an additional substituent at the 4-position (bromine or methoxy) to direct the regiochemistry of the quinone bisketal hydrolysis.The second method involves similar chemistry except that the anodic oxidation of a 4-methoxyphenol derivative directly affords the quinone monoketal.Hydrolysis of the trifluoroacetamide followed by an intramolecular condensation reaction affords the quinone imine ketal.Selected aspects of the chemistry of these compounds have been studied.Especially interesting is the reaction of a model quinone imine ketal with organolithium reagents.Either 1- or 2-substituted-5-methoxyindole is produced, depending upon the organolithium compound.