2020-90-8

Basic information

• Product Name: 1-(2,4,5-trimethoxyphenyl)propan-2-one
• Synonyms: 1-(2,4,5-trimethoxyphenyl)acetone; 2-propanone, 1-(2,4,5-trimethoxyphenyl)-
• CAS NO: 2020-90-8
• Molecular Formula: C₁₂H₁₆O₄
• Molecular Weight: 224.253
• Mol File: 2020-90-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 47-48 °C
• Boiling Point: 323.1°C at 760 mmHg
• Flash Point: 140.5°C
• Density: 1.078g/cm³
• Vapor Pressure: 0.000268mmHg at 25°C
• Refractive Index: 1.493
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-(2,4,5-trimethoxyphenyl)propan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,4,5-trimethoxyphenyl)propan-2-one(2020-90-8)
• EPA Substance Registry System: 1-(2,4,5-trimethoxyphenyl)propan-2-one(2020-90-8)

Safety Data

• Hazardous Substances Data: 2020-90-8(Hazardous Substances Data)

Usage

Description

1-(2,4,5-trimethoxyphenyl)propan-2-one, also known as TMA-2, is a synthetic psychedelic phenethylamine with a chemical structure akin to mescaline, a naturally occurring psychedelic compound found in the peyote cactus. TMA-2 is recognized for its hallucinogenic properties, which include altered perceptions, visual and auditory hallucinations, and shifts in mood and thought patterns. Despite its recreational use for its psychedelic effects, it is classified as a Schedule I controlled substance in the United States due to its potential for abuse and the absence of an accepted medical use.

Uses

Used in Recreational Applications:
TMA-2 is used as a recreational substance for its hallucinogenic effects, which include altered perceptions, visual and auditory hallucinations, and changes in mood and thought patterns. However, it is important to note that TMA-2 carries potential risks, such as psychological distress and physical health complications.
Used in Research Applications:
In the scientific community, TMA-2 may be used as a research chemical to study the effects of psychedelic substances on the human brain and their potential therapeutic applications. This can contribute to a better understanding of the underlying mechanisms of hallucinogenic experiences and their impact on mental health.

Upstream product

• 494-40-6 asarone 
• 1600-27-7 mercury(II) diacetate 
• 71-43-2 benzene 
• 134040-35-0 2,4,5-trimethoxy-β-methyl-β-nitrostyrene 
• 186581-53-3 diazomethane 
• 63359-53-5 2,4,5-trimethoxyphenylacetyl chloride 
• 146830-05-9 1-(2,4,5-Trimethoxyphenyl)-1,2-dihydroxypropane 
• 4463-16-5 2,4,5-trimethoxyphenylacetic acid 
• 2541-08-4 4-[(2,4,5-trimethoxy-phenyl)-thioacetyl]-morpholine 
• 2883-98-9 α-asarone 

Downstream Products

• 93675-32-2 2,4,5-trimethoxymethamphetamine 
• 1300021-20-8 (+/-)-2,4,5-trihydroxymethamphetamine hydrobromide 
• 1300021-22-0 C₁₀H₁₃NO₃ 
• 75014-06-1 (S)-ethyl 2-amino-2-mwthyl-3-(2,4,5-trimethoxyphenyl)propanoate 
• 75014-08-3 (R)-ethyl 2-amino-2-mwthyl-3-(2,4,5-trimethoxyphenyl)propanoate 
• 75014-04-9 (RS)-ethyl 2-amino-2-methyl-3-(2,4,5-trimethoxyphenyl)propanoate 
• 72746-40-8 (S)-6-OH-α-Me-Dopa 
• 752934-50-2 (R)-6-OH-α-Me-Dopa 
• 65520-36-7 (RS)-3-(2,4,5-trihydroxyphenyl)-2-methylalanine 
• 75014-03-8 (RS)-3-(2,4,5-trimethoxyphenyl)-2-methylalanine 
• 75014-02-7 (RS)-5-methyl-5-(2,4,5-trimethoxyphenyl)hydantoin 

Relevant articles and documents

Hepatic Metabolism of Carcinogenic β-Asarone

β-Asarone (1) belongs to the group of naturally occurring phenylpropenes like eugenol or anethole. Compound 1 is found in several plants, e.g., Acorus calamus or Asarum europaeum. Compound 1-containing plant materials and essential oils thereof are used to flavor foods and alcoholic beverages and as ingredients of many drugs in traditional phytomedicines. Although 1 has been claimed to have several positive pharmacological effects, it was found to be genotoxic and carcinogenic in rodents (liver and small intestine). The mechanism of action of carcinogenic allylic phenylpropenes consists of the metabolic activation via cytochrome P450 enzymes and sulfotransferases. In vivo experiments suggested that this pathway does not play a major role in the carcinogenicity of the propenylic compound 1 as is the case for other propenylic compounds, e.g., anethole. Since the metabolic pathways of 1 have not been investigated and its carcinogenic mode of action is unknown, we investigated the metabolism of 1 in liver microsomes of rats, bovines, porcines, and humans using 1H NMR, HPLC-DAD, and LC-ESI-MS/MS techniques. We synthesized the majority of identified metabolites which were used as reference compounds for the quantification and final verification of metabolites. Microsomal epoxidation of the side chain of 1 presumably yielded (Z)-asarone-1′,2′-epoxide (8a) which instantly was hydrolyzed to the corresponding erythro- and threo-configurated diols (9b, 9a) and the ketone 2,4,5-trimethoxyphenylacetone (13). This was the main metabolic pathway in the metabolism of 1 in all investigated liver microsomes. Hydroxylation of the side chain of 1 led to the formation of three alcohols at total yields of less than 30%: 1′-hydroxyasarone (2), (E)- and (Z)-3′-hydroxyasarone (4 and 6), with 6 being the mainly formed alcohol and 2 being detectable only in liver microsomes of Aroclor 1254-pretreated rats. Small amounts of 4 and 6 were further oxidized to the corresponding carbonyl compounds (E)- and (Z)-3′-oxoasarone (5, 7). 1′-Oxoasarone (3) was probably also formed in incubations with 1 but was not detectable, possibly due to its rapid reaction with nucleophiles. Eventually, three mono-O-demethylated metabolites of 1 were detected in minor concentrations. The time course of metabolite formation and determined kinetic parameters show little species-specific differences in the microsomal metabolism of 1. Furthermore, the kinetic parameters imply a very low dependence of the pattern of metabolite formation from substrate concentration. In human liver microsomes, 71-75% of 1 will be metabolized via epoxidation, 21-15% via hydroxylation (and further oxidation), and 8-10% via demethylation at lower as well as higher concentrations of 1, respectively (relative values). On the basis of our results, we hypothesize that the genotoxic epoxides of 1 are the ultimate carcinogens formed from 1.

Synthesis and neurotoxicity profile of 2,4,5-trihydroxymethamphetamine and its 6-(N-acetylcystein-S-yl) conjugate

The purpose of the present study was to determine if trihydroxymethamphetamine (THMA), a metabolite of methylenedioxymethamphetamine (MDMA, "ecstasy"), or its thioether conjugate, 6-(N-acetylcystein-S- yl)-2,4,5-trihydroxymethamphetamine (6-NAC-THMA), pla

Synthetic and preliminary hemodynamic and whole animal toxicity studies on (R, S)-, (R)-, and (S)-2-methyl-3-(2,4,5-trihydroxyphenyl)alanine

The synthesis, resolution, and absolute configuration assignment of 2-methyl-3-(2,4,5-trihydroxyphenyl)alanine (6-OH-α-Me-Dopa) are reported. Hemodynamic studies in the rat have shown that this structural analogue and potential metabolite of the clinicall