3937-16-4

Basic information

• Product Name: isomescaline
• Synonyms: isomescaline
• CAS NO: 3937-16-4
• Molecular Formula: C₁₁H₁₇NO₃
• Molecular Weight: 211.25758
• Mol File: 3937-16-4.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 301.6°Cat760mmHg
• Flash Point: 137.2°C
• Appearance: /
• Density: 1.067g/cm³
• Vapor Pressure: 0.00105mmHg at 25°C
• Refractive Index: 1.511
• CAS DataBase Reference: isomescaline(CAS DataBase Reference)
• NIST Chemistry Reference: isomescaline(3937-16-4)
• EPA Substance Registry System: isomescaline(3937-16-4)

Safety Data

• Hazardous Substances Data: 3937-16-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H17NO3/c1-13-9-5-4-8(6-7-12)10(14-2)11(9)15-3/h4-5H,6-7,12H2,1-3H3

Upstream product

• 118474-94-5 (E)-1-nitro-2-(2',3',4'-trimethoxyphenyl)ethene 
• 1111086-84-0 C₁₁H₁₅NO₆ 
• 1428796-91-1 (Z)-1,2,3-trimethoxy-4-(2-nitrovinyl)benzene 
• 634-36-6 1,2,3-trimethoxybenzene 
• 291301-33-2 C₂₁H₂₁N₃O₄ 
• 76474-95-8 methyl 3-(2,3,4-trimethoxyphenyl)propionate 
• 857813-99-1 3-(2,3,4-trimethoxy-phenyl)-propionic acid amide 
• 4668-08-0 1,2,3-trimethoxy-4-(2-nitro-vinyl)benzene 
• 116406-19-0 trans-2,3,4-trimethoxycinnamic acid 
• 33130-04-0 3-(2,3,4-trimethoxy-phenyl)-propionic acid 

Downstream Products

• 124237-41-8 N-<2-(2,3,4-trimethoxyphenyl)-ethyl>3,4-dimethoxy-2-hydroxy-methylphenylacetamide 
• 124237-43-0 N-<2-(2,3,4-trimethoxyphenyl)-ethyl>4,5-dimethoxy-2-hydroxymethylphenylacetamide 
• 74828-34-5 N-(2,3,4-trimethoxyphenethyl)(3',4'-methylenedioxyphenyl)acetamide 
• 107485-77-8 N-(2,3,4-trimethoxyphenethyl)acetamide 
• 148492-66-4 ethyl 3-oxo-3-<2'-(2'',3'',4''-trimethoxyphenyl)ethylamino>propanoate 
• 141172-49-8 2-(2',5'-dimethoxybenzoyl)-1-methylene-5,6,7-trimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 1428796-94-4 ethyl 7,8,9-trimethoxy-3-phenyl-5,6-dihydropyrrolo[2, 1-a]isoquinoline-2-carboxylate 
• 1428796-95-5 7,8,9-trimethoxy-3-phenyl-5,6-dihydropyrrolo[2,1-a]isoquinoline-2-carboxylic acid 
• 1428796-25-1 (R)-N-(1-hydroxy-3-(1H-indol-3-yl)propan-2-yl)-7,8,9-trimethoxy-3-phenyl-5,6-dihydropyrrolo[2,1-a]isoquinoline-2-carboxamide 
• 105166-67-4 4-Methyl-N-[2-(2,3,4-trimethoxy-phenyl)-ethyl]-benzenesulfonamide 
• 144344-74-1 N-<2-(2,3,4-trimethoxyphenyl)ethyl>-3-benzyloxybenzamide 
• 24237-31-8 N-<2-(2,3,4-trimethoxyphenyl)ethyl>-2-(3,4-dimethoxyphenyl)acetamide 
• 124237-42-9 N-<2-(2,3,4-trimethoxyphenyl)-ethyl>3,4-methylenedioxy-2-hydroxymethylphenylacetamide 
• 100009-74-3 N-(2',3',4'-trimethoxyphenethyl)-2-bromo-4-methoxybenzamide 

Relevant articles and documents

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.

The ethoxycarbonyl group as both activating and protective group in N-acyl-Pictet-Spengler reactions using methoxystyrenes. A short approach to racemic 1-benzyltetrahydroisoquinoline alkaloids

We present a systematic investigation on an improved variant of the N-acyl-Pictet-Spengler condensation for the synthesis of 1-benzyltetrahydroisoquinolines, based on our recently published synthesis of N-methylcoclaurine, exemplified by the total syntheses of 10 alkaloids in racemic form. Major advantages are a) using ω-methoxystyrenes as convenient alternatives to arylacetaldehydes, and b) using the ethoxycarbonyl residue for both activating the arylethylamine precursors for the cyclization reaction, and, as a significant extension, also as protective group for phenolic residues. After ring closure, the ethoxycarbonyl-protected phenols are deprotected simultaneously with the further processing of the carbamate group, either following route A (lithium alanate reduction) to give N-methylated phenolic products, or following route B (treatment with excess methyllithium) to give the corresponding alkaloids with free N-H function. This dual use of the ethoxycarbonyl group shortens the synthetic routes to hydroxylated 1-benzyltetrahydroisoquinolines significantly. Not surprisingly, these ten alkaloids did not show noteworthy effects on TPC2 cation channels and the tumor cell line VCR-R CEM, and did not exhibit P-glycoprotein blocking activity. But due to their free phenolic groups they can serve as valuable intermediates for novel derivatives addressing all of these targets, based on previous evidence for structure-activity relationships in this chemotype.

Novel total syntheses of oxoaporphine alkaloids enabled by mild Cu-catalyzed tandem oxidation/aromatization of 1-Bn-DHIQs

Novel total syntheses of oxoaporphine alkaloids such as liriodenine, dicentrinone, cassameridine, lysicamine, oxoglaucine and O-methylmoschatoline were developed. The key step of these total syntheses is Cu-catalyzed conversion of 1-benzyl-3,4-dihydro-isoquinolines (1-Bn-DHIQs) to 1-benzoyl-isoquinolines (1-Bz-IQs) via tandem oxidation/aromatization. This novel Cu-catalyzed conversion has been studied in detail, and was successfully used for constructing the 1-Bz-IQ core.