3213-29-4

Usage

Uses

Used in Pharmaceutical Synthesis:
2,3-Dimethoxyphenethylamine is used as a key intermediate in the synthesis of various pharmaceutical compounds, including N-(2,3-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide and N-(3,4-dimethoxyphenethyl)-phenyl acetamide. These compounds have potential applications in the development of new drugs for various medical conditions.
Used in Chemical Research:
As a component of bamboo plant extract, 2,3-dimethoxyphenethylamine may also be utilized in chemical research to better understand the properties and potential applications of compounds derived from natural sources. This can contribute to the discovery of novel bioactive molecules and the development of new therapeutic strategies.

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

• 2815-67-0 2,3-dimethoxynitrostyrene 
• 110600-36-7 (2,3-dimethoxy-phenyl)-acetaldehyde-oxime 
• 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 
• 7647-01-0 hydrogenchloride 
• 37630-20-9 1,2-Dimethoxy-3-((E)-2-nitro-vinyl)-benzene 
• 64-17-5 ethanol 
• 64-19-7 acetic acid 
• 5663-55-8 (2,3-dimethoxy-phenyl)-acetic acid amide 
• 4468-57-9 2-(2,3-dimethoxyphenyl)acetonitrile 

Downstream Products

• 102076-14-2 (2,3-dimethoxy-phenethyl)-furfuryl-methyl-amine 
• 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 
• 101585-07-3 4-[(2,3-dimethoxy-phenethylimino)-methyl]-phenol 
• 110492-04-1 2-[(2,3-dimethoxy-phenethylimino)-methyl]-6-methoxy-phenol 
• 859738-88-8 2,3-dimethoxy-benzoic acid-(2,3-dimethoxy-phenethylamide) 
• 109808-91-5 (2,3-dimethoxy-benzylidene)-(2,3-dimethoxy-phenethyl)-amine 
• 579-59-9 2,3-Dihydroxy-phenyl-ethylamin 
• 65713-30-6 2-chloro-N-(2,3-dimethoxyphenethyl)acetamide 
• 108974-42-1 5,6-dimethoxy-1-phenyl-isoquinoline 
• 109470-21-5 5,6-dimethoxy-1-phenyl-3,4-dihydro-isoquinoline 
• 143576-53-8 1-(2,3-dimethoxy-phenyl)-5,6-dimethoxy-isoquinoline 
• 855617-40-2 (5,6-dimethoxy-[1]isoquinolyl)-(3,4-dimethoxy-phenyl)-ketone 
• 10313-65-2 (5,6-dimethoxy-3,4-dihydro-[1]isoquinolyl)-(3,4-dimethoxy-phenyl)-ketone 

Relevant academic research and scientific papers

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.

Synthesis and Functional Characterization of 2-(2,5-Dimethoxyphenyl)-N-(2-fluorobenzyl)ethanamine (25H-NBF) Positional Isomers

Serotonergic psychedelics, substances exerting their pharmacological action through activation of the serotonin 2A receptor (5-HT2AR), have continuously comprised a substantial fraction of the over 1000 reported New Psychoactive Substances (NPS) so far. Within this category, N-benzyl derived phenethylamines, such as NBOMes and NBFs, have shown to be of particular relevance. As these substances remain incompletely characterized, this study aimed at synthesizing positional isomers of 25H-NBF, with two methoxy groups placed on different positions of the phenyl group of the phenethylamine moiety. These isomers were then functionally characterized in an in vitro bioassay monitoring the recruitment of β-Arrestin 2 to the 5-HT2AR through luminescent readout via the NanoBiT technology. The obtained results provide insight into the optimal substitution pattern of the phenyl group of the phenethylamine moiety of N-benzyl derived substances, a feature so far mostly explored in the phenethylamines underived at the N-position. In the employed bioassay, the most potent substances were 24H-NBF (EC50 value of 158 nM), 26H-NBF (397 nM), and 25H-NBF (448 nM), with 23H-NBF, 35H-NBF, and 34H-NBF yielding μM EC50 values. A similar ranking was obtained for the compounds' efficacy: Taking as a reference LSD (lysergic acid diethylamide), 24H-, 26H-, and 25H-NBF had an efficacy of 106-107%, followed by 23H-NBF (96.1%), 34H-NBF (75.2%), and 35H-NBF (58.9%). The stronger activity of 24H-, 25H-, and 26H-NBF emphasizes the important role of the methoxy group at position 2 of the phenethylamine moiety for the in vitro functionality of NBF substances.

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.

Substituted 1-(aminomethyl)-2-(arylacetyl)-1,2,3,4- tetrahydroisoquinolines: A novel class of very potent antinociceptive agents with varying degrees of selectivity for κ and μ opioid receptors

This study describes the synthesis of a series of novel substituted 1- (aminomethyl)-2-(arylacetyl)-1,2,3,4-tetrahydroisoquinolines, and discusses their structure-activity relationships (SARs) using binding affinity for opioid receptors and antinociceptive potency as the indices of biological activity. The introduction of a hydroxy substituent in position 5 of the isoquinoline nucleus generated a compound, 40, which is 2 times more potent than the previously disclosed unsubstituted analogue 39 in mouse models of antinociception. A QSAR analysis of the 5-substitution clearly demonstrates that antinociceptive activity is inversely associated with the lipophilicity of the substituents. The substituted compounds described herein are less selective for the κ opioid receptors than the unsubstituted isoquinoline 39. For example, the 5-hydroxy-substituted compound 59 shows high affinity for κ opioid receptors (K(i) κ = 0.09 nM) and a (K(i) μ/K(i) κ ratio of only 5. However, a multiple linear regression analysis demonstrates a lack of correlation between antinociceptive activity and affinity for the μ opioid receptor. On the other hand, the correlation between binding affinity to κ opioid receptor and antinociceptive activity was statistically significant.

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.