6957-27-3

Basic information

• Product Name: 1-[(3,4-Dimethoxyphenyl)methyl]-3,4-dihydro-6,7-dimethoxyisoquinoline
• Synonyms: 1-[(3,4-dimethoxyphenyl)methyl]-3,4-dihydro-6,7-dimethoxyisoquinoline;3,4-Dihydropapaverine;Dihydropapaverine;2,4-DIHYDROPAPAVERINE;3,4-Dihydro-6,7-dimethoxy-1-(3,4-dimethoxybenzyl)isoquinoline;1-(3,4-Dimethoxybenzyl)-6,7-dimethoxy-3,4-dihydroisoquinoline;3,4-DIHYDROPAPAVERINE(WXG01659);1-(3,4-Dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxyisoquinoline
• CAS NO: 6957-27-3
• Molecular Formula: C₂₀H₂₃NO₄
• Molecular Weight: 341.40092
• EINECS: 230-148-3
• Mol File: 6957-27-3.mol
• Article Data: 42

Chemical Properties

• Melting Point: 98-99 °C
• Boiling Point: 482.6 °C at 760 mmHg
• Flash Point: 196.9 °C
• Appearance: /
• Density: 1.15 g/cm³
• Vapor Pressure: 5.28E-09mmHg at 25°C
• PKA: 6.12±0.20(Predicted)
• CAS DataBase Reference: 1-[(3,4-Dimethoxyphenyl)methyl]-3,4-dihydro-6,7-dimethoxyisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(3,4-Dimethoxyphenyl)methyl]-3,4-dihydro-6,7-dimethoxyisoquinoline(6957-27-3)
• EPA Substance Registry System: 1-[(3,4-Dimethoxyphenyl)methyl]-3,4-dihydro-6,7-dimethoxyisoquinoline(6957-27-3)

Safety Data

• Hazardous Substances Data: 6957-27-3(Hazardous Substances Data)

Usage

Uses

3,4-Dihydropapaverine is an impurity of Papaverine (P190500), smooth muscle relaxant found in opium. Vasodilator (cerebral).

InChI:InChI=1/C20H23NO4.BrH/c1-22-17-6-5-13(10-18(17)23-2)9-16-15-12-20(25-4)19(24-3)11-14(15)7-8-21-16;/h5-6,10-12H,7-9H2,1-4H3;1H

Upstream product

• 139-76-4 N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide 
• 796074-04-9 (2,3-dimethoxy-phenyl)-acetic acid-(2,3-dimethoxy-phenethylamide) 
• 93-17-4 3,4-dimethoxyphenylacetonitrile 
• 7417-21-2 2-(3,4-dimethoxyphenyl)ethyl alcohol 
• 50896-90-7 (-) N-norlaudanosine 
• 76579-53-8 2-(3,4-dimethoxyphenyl)-N,N-dimethylethanethioamide 
• 85621-43-8 3,4-dihydroxyphenylacetic acid diacetate 
• 14773-41-2 3-(3,4-dimethoxyphenyl)propionic acid amide 
• 6831-56-7 2',3'-dimethoxyphenylacetyl chloride 
• 90-53-9 2,3-dimethoxyphenylacetic acid 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 7306-46-9 4-chloromethyl-1,2-dimethoxy-benzene 
• 91-16-7 1,2-dimethoxybenzene 
• 5763-61-1 3,4-dimethoxybenzylamine 

Downstream Products

• 17366-51-7 (Z)-2-Acetyl-1-<(3,4-dimethoxyphenyl)methylene>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 858520-96-4 ethyl 1-(3,4-dimethoxyphenyl)-2-(2-benzyloxy-4,5-dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate 
• 519753-09-4 2-[1-(3,4-dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinolin-2-yl]phenyl ethyl carbonate 
• 519753-21-0 2-[1-(3,4-dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinolin-2-yl]-4,5-dimethoxyphenyl ethyl carbonate 
• 858520-87-3 ethyl 1-(3,4-dimethoxyphenyl)-2-(2,4-dibenzyloxy-5-methoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate 
• 85544-30-5 (3,4-dimethoxy-phenyl)-(6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-methanone 
• 58-74-2 Papaverine 
• 522-57-6 papaveraldine 
• 482-76-8 papaverinol 
• 15248-39-2 6,7-dimethoxyisoquinoline 
• 91-16-7 1,2-dimethoxybenzene 
• 61-25-6 papaverine hydrochloride 
• 523-02-4 2,3,10,11-tetramethoxy-5,6,7,8,13,13a-hexahydroisoquinolino[3,2-a]isoquinoline 
• 681431-24-3 1-(3,4-dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylic acid ethyl ester 

Relevant articles and documents

COMPOUNDS, COMPOSITIONS AND METHODS FOR TREATING NASH, NAFLD, AND OBESITY

The present technology relates to methods of treating NASH, NAFLD and/or obesity using compounds of Formulas I, II, III, IV, V, and/or VI. The methods include administering to a subject suffering from one or more of non-alcoholic steatohepatitis (NASH), non- alcoholic fatty liver disease (NAFLD) and/or obesity a therapeutically effective amount of such a compound

Copper(ii)-catalyzed and acid-promoted highly regioselective oxidation of tautomerizable C(sp3)-H bonds adjacent to 3,4-dihydroisoquinolines using air (O2) as a clean oxidant

A mild, efficient and eco-friendly method for the oxidation of 1-Bn-DHIQs to 1-Bz-DHIQs without concomitant excessive oxidation of 1-Bz-DHIQs to 1-Bz-IQs is very important for the syntheses of 1-Bz-DHIQ alkaloids and analogues. In this article, we developed a novel Cu(ii)-catalyzed and acid-promoted highly regioselective oxidation of tautomerizable C(sp3)-H bonds adjacent to the C-1 positions of various 1-Bn-DHIQs. It was observed that when 0.2 equiv. of Cu(OAc)2·2H2O was used as the catalyst, 3.0 equiv. of AcOH was used as the additive and air (O2) was used as a clean oxidant, various 1-Bn-DHIQs could be efficiently oxidized to corresponding 1-Bz-DHIQs at 25 °C in DMSO. Especially, almost no concomitant excessive oxidation of 1-Bz-DHIQs to 1-Bz-IQs was observed during the above reaction. In addition, this method was successfully applied in the first total synthesis of the alkaloid canelillinoxine.

One-Pot Synthesis of Papaverine Hydrochloride and Identification of Impurities

Abstract: A one-pot synthesis of papaverine hydrochloride with 99.6% purity was performed using xylene as solvent for the entire process. The critical parameters of each step, as well as the impurities generated, were identified. The overall yield was improved to 63%. The proposed synthetic procedure is suitable for industrial production.