54-04-6

Basic information

• Product Name: 3,4,5-TRIMETHOXYPHENETHYLAMINE, HYDROCHLORIDE
• Synonyms: 1-amino-2-(3,4,5-trimethoxyphenyl)-ethan;2-(3,4,5-Trimethoxyphenyl)ethanamine;3,4,5-trimethoxy-benzeneethanamin;3,4,5-Trimethoxybenzeneethanamine;3,4,5-trimethoxy-phenethylamin;3,4,5-Trimethoxyphenethylamine;3,4,5-Trimethoxyphenylethylamine;Ethane, 1-amino-2-(3,4,5-trimethoxyphenyl)-
• CAS NO: 54-04-6
• Molecular Formula: C₁₁H₁₇NO₃
• Molecular Weight: 211.25758
• EINECS: 200-190-7
• Mol File: 54-04-6.mol
• Article Data: 18

Chemical Properties

• Melting Point: 35-36°
• Boiling Point: bp12 180°
• Flash Point: 145.8°C
• Appearance: /
• Density: 1.1240 (rough estimate)
• Vapor Pressure: 0.000293mmHg at 25°C
• Refractive Index: 1.5718 (estimate)
• PKA: 9.57±0.10(Predicted)
• CAS DataBase Reference: 3,4,5-TRIMETHOXYPHENETHYLAMINE, HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5-TRIMETHOXYPHENETHYLAMINE, HYDROCHLORIDE(54-04-6)
• EPA Substance Registry System: 3,4,5-TRIMETHOXYPHENETHYLAMINE, HYDROCHLORIDE(54-04-6)

Safety Data

• Hazardous Substances Data: 54-04-6(Hazardous Substances Data)

Usage

Description

Mescaline is one of the main active ingredients in the peyote plant, Lophophora williamsii. It is also found in several other cacti including the South American Trichocereus otherwise known as the Peruvian torch species. Mescaline can also be synthesized in the laboratory. It is one of the oldest known hallucinogenic drugs. Ingestion of mescaline via use of the peyote cactus has been used in rituals by North American Indians dating back thousands of years. Ingestion of peyote was also common among the Aztec, Apache, and Pima Indians for religious, ceremonial, and medicinal purposes. Mescaline was isolated from peyote in 1896 by the chemist Hefter and in 1919, the chemical structure was confirmed by Spath. There are many analogs of mescaline with over 250 being prepared and self-tested by the chemist and pharmacologist, Alexander Shulgin (aka Sasha Shulgin). Mescaline became a Schedule I drug and was placed in Controlled Substances Act in 1970. Many of the related chemicals or analogs of mescaline were also placed in Schedule I of the Controlled Substances Act.

Chemical Properties

White Powder

Uses

Different sources of media describe the Uses of 54-04-6 differently. You can refer to the following data:
1. Psychedelic Alkoloid
2. Mescaline is used recreationally as a hallucinogenic drug and it is used in religious ceremonies for spiritual purposes by groups such as the Native American church. Mescaline is purported not to have any therapeutic benefits based on its Schedule I status. When used recreationally typical doses range from 300 to 500 mg orally.

Definition

ChEBI: A phenethylamine alkaloid that is phenethylamine substituted at positions 3, 4 and 5 by methoxy groups.

Hazard

Highly toxic by ingestion.

Safety Profile

Poison by intraperitoneal and intravenous routes. Moderately toxic by ingestion route. An experimental teratogen. Other experimental reproductive effects. Human systemic effects by intramuscular route: euphoria and hallucinations, dstorted perceptions. A psychotoimetic agent (a drug of abuse). When heated to decomposition it emits toxic fumes of NOx.

Environmental Fate

The primary exposure pathway is oral via ingestion of the chemical powder or salt or via ingestion of peyote ‘ buttons.’ These buttons are the round, fleshy tops of the cactus that are sliced and dried. Multiple buttons of peyote are typically ingested due to the relatively small content (i.e., 40–50 mg) of individual peyote buttons.

Toxicity evaluation

The exact mechanism of mescaline has not been clearly defined. The central nervous system effects of mescaline appear to involve stimulation of both serotonin and dopamine receptors. In experimental studies, these effects can be blocked by either serotonin antagonists such as methysergide or dopamine antagonists such as haloperidol. Mescaline is structurally related to the amphetamines and cathine and cathinone, which are found in the plant Catha edulis. Mescaline is a ring-substituted phenethylamine. Sympathomimetic effects can occur and are thought to be centrally mediated. High doses of peyote/mescaline can produce more pronounced sympathomimetic effects such as tachycardia and hypertension. Hallucinations may be associated with homicidal, suicidal, or psychotic behaviors. There have been no reported deaths due to the physiological effects of peyote/mescaline. Traumatic deaths have occurred secondary to hallucinations. Mescaline does not appear to inhibit monoamine oxidase.

InChI:InChI=1/C11H17NO3/c1-5-12-8-6-9(13-2)11(15-4)10(7-8)14-3/h6-7,12H,5H2,1-4H3

Upstream product

• 40663-31-8 1-(3,4,5-trimethoxyphenyl)-2-nitroethene 
• 13338-63-1 2-(3,4,5-trimethoxyphenyl)acetonitrile 
• 18111-22-3 3,4,5-trimethoxy-phenylalanine 
• 5990-01-2 N-(3,4,5-trimethoxy-phenethyl)-benzamide 
• 832-92-8 mescaline hydrochloride 
• 1436392-06-1 benzyl 3,4,5-trimethoxyphenethylcarbamate 
• 91958-61-1 acetoxy-3,4,5-trimethoxyphenylacetonitrile 
• 106213-58-5 3-(3,4,5-trimethoxyphenyl)propanamide 
• 91248-14-5 2-(3,4,5-trimethoxyphenyl)acetamide 
• 6316-70-7 3,4,5-trimethoxy-β-nitrostyrene 
• 40174-10-5 2-(3,4,5-trimethoxyphenyl)ethyl methanesulfonate 
• 1136-86-3 methyl (3,4,5-trimethoxyphenyl) ketone 
• 910866-99-8 5-(2-azidoethyl)-1,2,3-trimethoxybenzene 
• 37785-48-1 2-(3,4,5-trimethoxyphenyl)ethanol 

Downstream Products

• 2413-00-5 2-(4-Hydroxy-3,5-dimethoxyphenyl)ethanamin 
• 1927-04-4 5-hydroxydopamine 
• 734477-60-2 2,6-dibromo-3,4,5-trimethoxy-phenethylamine 
• 118-41-2 Eudesmic acid 
• 4593-89-9 N-acetylmescaline 
• 62028-41-5 N-(3,4,5-trimethoxy-phenethyl)-propionamide 
• 6308-78-7 trimethyl-(3,4,5-trimethoxy-phenethyl)-ammonium; iodide 
• 101256-83-1 N-(3,4,5-trimethoxy-phenethyl)-malonamic acid ethyl ester 
• 35174-89-1 (4-methoxy-phenyl)-acetic acid-(3,4,5-trimethoxy-phenethylamide) 
• 91025-54-6 N-(3,4,5-trimethoxyphenethyl)-5-phenyl-4-hydroxypentanamide 
• 84752-45-4 ethyl N-(3,4,5-trimethoxyphenethyl)-2,2-dimethylmalonamate 
• 84752-38-5 N-(3,4,5-trimethoxyphenethyl)-3,3-(ethylenedioxy)-5-hydroxy-2,2-dimethylpentanamide 
• 79831-93-9 4,5-dimethoxy-2-nitro-N-(3,4,5-trimethoxyphenethyl)phenylacetamide 
• 79831-92-8 5-benzyloxy-4-methoxy-2-nitro-N-(3,4,5-trimethoxyphenethyl)phenylacetamide 

Relevant articles and documents

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Synthesis, binding, and functional properties of tetrahydroisoquinolino-2-alkyl phenones as selective σ2R/TMEM97 ligands

Sigma-2 receptor (σ2R/TMEM97) has been implicated to play important roles in multiple cellular dysfunctions, such as cell neoplastic proliferation, neuro-inflammation, neurodegeneration, etc. Selective σ2 ligands are believed to be promising pharmacological tools to regulate or diagnose various disorders. As an ongoing effort of discovery of new and selective σ2 ligands, we have synthesized a series of tetrahydroisoquinolino-2-alkyl phenone analogs and identified that 10 of them have moderate to potent affinity and selectivity for σ2R/TMEM97. Especially, 4 analogs showed Ki values ranging from 0.38 to 5.1 nM for σ2R/TMEM97 with no or low affinity for sigma-1 receptor (σ1R). Functional assays indicated that these 4 most potent analogs had no effects on intracellular calcium concentration and were classified as putative σ2R/TMEM97 antagonists according to current understanding. The σ2R/TMEM97 has been suggested to play important roles in the central nervous system. Based on published pharmacological and clinical results from several regarded σ2R/TMEM97 antagonists, these analogs may potentially be useful for the treatment of various neurodegenerative diseases.

Synthesis of Functionalized Indolines and Dihydrobenzofurans by Iron and Copper Catalyzed Aryl C-N and C-O Bond Formation

A simple and effective one-pot, two-step intramolecular aryl C-N and C-O bond forming process for the preparation of a wide range of benzo-fused heterocyclic scaffolds using iron and copper catalysis is described. Activated aryl rings were subjected to a highly regioselective, iron(III) triflimide-catalyzed iodination, followed by a copper(I)-catalyzed intramolecular N-or O-arylation step leading to indolines, dihydrobenzofurans, and six-membered analogues. The general applicability and functional group tolerance of this method were exemplified by the total synthesis of the neolignan natural product, (+)-obtusafuran. DFT calculations using Fukui functions were also performed, providing a molecular orbital rationale for the highly regioselective arene iodination process.