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

3,4,5-TRIMETHOXYPHENETHYLAMINE, HYDROCHLORIDE is a phenethylamine alkaloid that is phenethylamine substituted at positions 3, 4, and 5 by methoxy groups. It is a white powder and is known for its psychedelic effects.

Uses

Used in Psychedelic Alkaloids:
3,4,5-TRIMETHOXYPHENETHYLAMINE, HYDROCHLORIDE is used as a psychedelic alkaloid for recreational purposes. It is known for inducing hallucinogenic effects and altering perceptions, thoughts, and emotions.
Used in Religious Ceremonies:
In some cultures, 3,4,5-TRIMETHOXYPHENETHYLAMINE, HYDROCHLORIDE is used as a hallucinogenic substance in religious ceremonies for spiritual purposes. It is believed to facilitate a deeper connection with the divine and enhance spiritual experiences.
Used in Scientific Research:
3,4,5-TRIMETHOXYPHENETHYLAMINE, HYDROCHLORIDE is also used in scientific research to study the effects of psychedelic substances on the human brain and their potential therapeutic applications. Researchers are exploring its potential in treating various mental health disorders, such as depression, anxiety, and post-traumatic stress disorder (PTSD).
Please note that the use of 3,4,5-TRIMETHOXYPHENETHYLAMINE, HYDROCHLORIDE may be subject to legal restrictions and regulations depending on the jurisdiction. It is essential to be aware of and comply with the relevant laws and guidelines when using this substance.

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 
• 6316-70-7 3,4,5-trimethoxy-β-nitrostyrene 
• 91248-14-5 2-(3,4,5-trimethoxyphenyl)acetamide 
• 18111-22-3 3,4,5-trimethoxy-phenylalanine 
• 5990-01-2 N-(3,4,5-trimethoxy-phenethyl)-benzamide 
• 106213-58-5 3-(3,4,5-trimethoxyphenyl)propanamide 
• 91958-61-1 acetoxy-3,4,5-trimethoxyphenylacetonitrile 
• 7664-93-9 sulfuric acid 
• 64-19-7 acetic acid 
• 7647-01-0 hydrogenchloride 
• 60-29-7 diethyl ether 
• 63909-39-7 1,2,3-trimethoxy-5-(2-nitroethyl)benzene 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 

Downstream Products

• 80548-66-9 N-(3,4,5-trimethoxy-phenethyl)-butyramide 
• 642-30-8 6,7,8-trimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 2609-41-8 (3,4,5-trimethoxy-phenethyl)-carbamic acid ethyl ester 
• 4593-89-9 N-acetylmescaline 
• 5990-01-2 N-(3,4,5-trimethoxy-phenethyl)-benzamide 
• 62028-41-5 N-(3,4,5-trimethoxy-phenethyl)-propionamide 
• 6308-78-7 trimethyl-(3,4,5-trimethoxy-phenethyl)-ammonium; iodide 
• 101450-61-7 N-(3,4,5-trimethoxy-phenethyl)-isovaleramide 
• 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) 
• 59801-49-9 4-(3,4,5-trimethoxy-phenethyl)-thiomorpholine 1,1-dioxide 
• 66265-87-0 1-(4-Hydroxy-3-methylsulfanyl-phenyl)-2-[2-(3,4,5-trimethoxy-phenyl)-ethylamino]-ethanone 
• 84752-40-9 ethyl 3-<(3,4,5-trimethoxyphenethyl)amino>propionate 
• 734477-60-2 2,6-dibromo-3,4,5-trimethoxy-phenethylamine 

Relevant articles and documents

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Structure–activity relationship and biological evaluation of berberine derivatives as PCSK9 down-regulating agents

Proprotein convertase subtilisin/kexin type 9 (PCSK9) is a secreted protein and its deficiency markedly enhanced the survival rate of patient with cardiovascular diseases (CVDs). Forty berberine (BBR) derivatives were synthesized and evaluated for their activities on down-regulating the transcription of PCSK9 in HepG2 cells, taking BBR as the lead. Structure–activity relationship (SAR) analysis revealed that 2,3-dimethoxy moiety might be beneficial for activity. Among them, 9k displayed the most potent activity with IC50 value of 9.5 ± 0.5 μM, better than that of BBR. Also, it significantly decreased PCSK9 protein level at cellular level, as well as in the liver and serum of mice in vivo. Furthermore, 9k markedly increased LDLR expression and LDL-C clearance via down-regulating PCSK9 protein. The mechanism of action of 9k is targeting HNF1α and/or Sp1 cluster modulation upstream of PCSK9, a different one from BBR. Therefore, 9k might have the potential to be a novel PCSK9 transcriptional inhibitor for the treatment of atherosclerosis, worthy for further investigation.

Design, synthesis and evaluation of thiourea derivatives as antimicrobial and antiviral agents

Background: The development of drug-resistant by bacteria appears rapidly and thus making the effectiveness of antibiotics severely limited. Methods: A series of thiourea derivatives was synthesized, characterized and evaluated for their in vitro antibacterial, antifungal and antiviral activities. Results: Structures of the newly synthesized compounds were confirmed by elemental and spectral analysis. The biological results showed that some of the target compounds displayed comparable antimicrobial and antiviral activities with reference drugs. Structure-activity relationship studies revealed that the ortho-chloro or fluoro substituted phenyl at Ar1 and substituted pyridinyl at Ar2 positions of the thiourea nucleus are essential for their in vitro antimicrobial and anti-HIV activity. In particular, compounds 8 and 10 showed better activity against the tested bacteria, fungi and viral strains than other synthesized PET derivatives reported in the present study. Conclusion: These results provide an encouraging lead that could be used for the development of new potent antiviral and antimicrobial agents.