3213-29-4

Basic information

• Product Name: 2,3-DIMETHOXYPHENETHYLAMINE
• Synonyms: 2,3-Dimethoxyphenethylamine ,98%;2,3-Dimethoxyphenethylamine 97%;RARECHEM AL BW 0356;2,3-DIMETHOXYPHENETHYLAMINE;2-(2,3-Dimethoxyphenyl)ethanamine;2-(2,3-dimethoxyphenyl)ethylamine
• CAS NO: 3213-29-4
• Molecular Formula: C₁₀H₁₅NO₂
• Molecular Weight: 181.23
• Product Categories: Amines;C9 to C10;Nitrogen Compounds
• Mol File: 3213-29-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 261-262 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.178 g/mL
• Vapor Pressure: 0.00829mmHg at 25°C
• Refractive Index: n20/D 1.5320(lit.)
• CAS DataBase Reference: 2,3-DIMETHOXYPHENETHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIMETHOXYPHENETHYLAMINE(3213-29-4)
• EPA Substance Registry System: 2,3-DIMETHOXYPHENETHYLAMINE(3213-29-4)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2735 8/PG 2
• WGK Germany: 3
• HazardClass: AIR SENSITIVE, CORROSIVE
• Hazardous Substances Data: 3213-29-4(Hazardous Substances Data)

Usage

Uses

2,3-Dimethoxyphenethylamine may be used in the synthesis of N-(2,3-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide and N-(3,4-dimethoxyphenethyl)-phenyl acetamide.

General Description

2,3-Dimethoxyphenethylamine is identified as one of the components in bamboo (Phyllostachys pubescens) plant extract by gas chromatographic- mass spectrometric analysis. 1-(2,3-dimethoxyphenyl)-2-nitroethene undergoes reduction reaction with lithium aluminum hydride (LiAlH4) in the presence of dry tetrahydrofuran to yield 2,3-dimethoxyphenethylamine.

InChI:InChI=1/C10H15NO2/c1-12-9-5-3-4-8(6-7-11)10(9)13-2/h3-5H,6-7,11H2,1-2H3

Upstream product

• 64-17-5 ethanol 
• 37630-20-9 1,2-Dimethoxy-3-((E)-2-nitro-vinyl)-benzene 
• 64-19-7 acetic acid 
• 7647-01-0 hydrogenchloride 
• 14255-59-5 2-(2,3-dimethoxyphenyl)-1-nitroethane 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 3893-01-4 2,3-dimethoxybenzyl chloride 
• 5653-67-8 2,3-dimethoxybenzyl alcohol 
• 6831-56-7 2',3'-dimethoxyphenylacetyl chloride 
• 110600-36-7 (2,3-dimethoxy-phenyl)-acetaldehyde-oxime 
• 5663-55-8 (2,3-dimethoxy-phenyl)-acetic acid amide 
• 2815-67-0 2,3-dimethoxynitrostyrene 
• 4468-57-9 2-(2,3-dimethoxyphenyl)acetonitrile 

Downstream Products

• 63905-67-9 5,6-dimethoxy-1,2,3,4-tetrahydro-isoquinoline hydrochloride 
• 876479-49-1 (3,4-dimethoxy-2-nitro-phenyl)-acetic acid-(2,3-dimethoxy-phenethylamide) 
• 10313-64-1 N-(2,3-dimethoxyphenylethyl)-2-(3,4-dimethoxyphenyl)acetamide 
• 110492-04-1 2-[(2,3-dimethoxy-phenethylimino)-methyl]-6-methoxy-phenol 
• 108838-22-8 N-(2,3-dimethoxy-phenethyl)-isovaleramide 
• 109808-91-5 (2,3-dimethoxy-benzylidene)-(2,3-dimethoxy-phenethyl)-amine 
• 10313-60-7 3,4-dimethoxyphenylacetyl chloride 
• 1222374-82-4 C₁₁H₁₆N₂O₂S 
• 1256778-14-9 N-[2-(3,4,-dimethoxyphenyl)-ethyl]-2-(4-fluorophenyl)-2-formylaminoacetamide 
• 857782-20-8 (2,3-dimethoxy-phenethyl)-carbamic acid ethyl ester 
• 261953-72-4 N-(2,3-dimethoxy-phenethyl)-acetamide 
• 3490-09-3 (2,3-dimethoxy-phenethyl)-methyl-amine 
• 69226-56-8 (2,3-dimethoxy-phenethyl)-urea 
• 796074-04-9 (2,3-dimethoxy-phenyl)-acetic acid-(2,3-dimethoxy-phenethylamide) 

Relevant articles and documents

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.

SAR based design of nicotinamides as a novel class of androgen receptor antagonists for prostate cancer

Molecular knowledge of pure antagonism and systematic SAR study offered a direction for structural optimization of DIMN to provide nicotinamides as a novel series of AR antagonists. Nicotinamides with extended linear scaffold bearing sterically bulky alkoxy groups on isoquinoline end were synthesized for H12 displacement. AR binding affinity and molecular basis of antiandrogenic effect establish the optimized derivatives, 7au and 7bb, as promising candidates of second generation AR antagonists for advanced prostate cancer.

A Facile Sythesis of 1,2,3,4-Tetrahydroisoquinolines Through Cyclization of O,N-Acetals

A mild and efficient method for the synthesis of 1,2,3,4-tetrahydroisoquinolines by a modified Pictet-Spengler reaction involving Lewis acid-mediated cyclization of O,N-acetals is described.