7668-87-3

Basic information

• Product Name: N-(3,4,5-Trimethoxyphenylacetyl)homoveratrylamine
• Synonyms: N-(3,4,5-Trimethoxyphenylacetyl)homoveratrylamine;N-(3,4-Dimethoxyphenethyl)-2-(3,4,5-trimethoxyphenyl)acetamide;N-[2-(3,4-Dimethoxyphenyl)ethyl]-3,4,5-trimethoxy-benzeneacetamide;N-[2-(3,4-DiMethoxyphenyl)ethyl]-3,4,5-triMethoxy-
• CAS NO: 7668-87-3
• Molecular Formula: C₂₁H₂₇NO₆
• Molecular Weight: 389.44
• Product Categories: Aromatics Compounds;Aromatics;Intermediates
• Mol File: 7668-87-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 100.5-101.5 °C
• Boiling Point: 580.139°C at 760 mmHg
• Flash Point: 304.657°C
• Appearance: /
• Density: 1.139g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.536
• Solubility: Dichloromethane, Methanol
• PKA: 15.22±0.46(Predicted)
• CAS DataBase Reference: N-(3,4,5-Trimethoxyphenylacetyl)homoveratrylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3,4,5-Trimethoxyphenylacetyl)homoveratrylamine(7668-87-3)
• EPA Substance Registry System: N-(3,4,5-Trimethoxyphenylacetyl)homoveratrylamine(7668-87-3)

Safety Data

• Hazardous Substances Data: 7668-87-3(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

InChI:InChI=1/C21H27NO6/c1-24-16-7-6-14(10-17(16)25-2)8-9-22-20(23)13-15-11-18(26-3)21(28-5)19(12-15)27-4/h6-7,10-12H,8-9,13H2,1-5H3,(H,22,23)

Upstream product

• 951-82-6 3,4,5-trimethoxyphenyl acetic acid 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 39053-78-6 3,4,5-trimethoxyphenylacetyl chloride 

Downstream Products

• 61349-11-9 1-(3',4',5'-trimethoxybenzyl)-3,4-dihydro-6,7-dimethoxyisoquinoline 
• 73554-57-1 6,7-dimethoxy-1-(3',4',5'-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline 
• 81165-39-1 3-[6,7-Dimethoxy-1-(3,4,5-trimethoxy-benzyl)-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid 2-{3-[6,7-dimethoxy-1-(3,4,5-trimethoxy-benzyl)-3,4-dihydro-1H-isoquinolin-2-yl]-propionyloxy}-ethyl ester; compound with oxalic acid 
• 64229-10-3 C₅₂H₇₀N₂O₁₄⁽²⁺⁾*2CH₃O₃S^(1-) 
• 7668-88-4 rac-6,7-dimethoxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride 
• 76129-86-7 N-formyl-6,7-dimethoxy-1-(3',4',5'-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline 
• 53392-39-5 6,7-dimethoxy-1-(3', 4', 5'-trimethoxybenzyl)2-methyl, 3,4-dihydroisoquinolinium iodide 
• 108704-76-3 6,7-dimethoxy-1-(3,4,5-trimethoxybenzyl)-3,4-dihydroisoquinoline hydrochloride 
• 188956-91-4 (R)-6,7-dimethoxy-1-(3',4',5'-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline 
• 104832-01-1 (R)-N-methyl-6,7-dimethoxy-1-(3',4',5'-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinolinium 2,3-dibenzoyl-L-tartarate 
• 24734-71-2 N-methyl-6,7-dimethoxy-1-(3',4',5'-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

Effect of 1-Substitution on Tetrahydroisoquinolines as Selective Antagonists for the Orexin-1 Receptor

Selective blockade of the orexin-1 receptor (OX1) has been suggested as a potential approach to drug addiction therapy because of its role in modulating the brain's reward system. We have recently reported a series of tetrahydroisoquinoline-based OX1 selective antagonists. Aimed at elucidating structure-activity relationship requirements in other regions of the molecule and further enhancing OX1 potency and selectivity, we have designed and synthesized a series of analogues bearing a variety of substituents at the 1-position of the tetrahydroisoquinoline. The results show that an optimally substituted benzyl group is required for activity at the OX1 receptor. Several compounds with improved potency and/or selectivity have been identified. When combined with structural modifications that were previously found to improve selectivity, we have identified compound 73 (RTIOX-251) with an apparent dissociation constant (Ke) of 16.1 nM at the OX1 receptor and >620-fold selectivity over the OX2 receptor. In vivo, compound 73 was shown to block the development of locomotor sensitization to cocaine in rats. (Chemical Equation Presented).

Novel hybrids from lamellarin D and combretastatin A 4 as cytotoxic agents

A new series of hybrids of lamellarin D and combretastatin A 4, 1,2-diphenyl-5,6-dihydropyrrolo [2,1-a] isoquinolines, were designed as cytotoxic agents based on principles of combination in medicinal chemistry and taking the parent compounds' different anti-proliferative mechanisms into consideration. Twenty-two novel hybrids were synthesized through a convenient route, with a key step of core pyrrole formation and evaluated for their anti-proliferative activities in vitro against K-562, A-549, SMMC-7721, SGC-7901 and HCT-116 cancer cell lines. The results showed that some hybrids had good anti-proliferative activities in low IC50 ranges.

Studies on Protoberberine Alkaloids : Synthesis of Glabrine Dimethyl Ether

2,3,9,10,11-Pentamethoxyprotoberberinium salt (III) has been synthesized from homoveratrylamine and 3,4,5-trimethoxyphenylacetic acid through the intermediacy of an N-formyl-benzyltetrahydroisoquinoline derivative (VI).The synthetic material is identical