482-76-8

Basic information

• Product Name: alpha-(3,4-dimethoxyphenyl)-6,7-dimethoxyisoquinoline-1-methanol
• Synonyms: alpha-(3,4-dimethoxyphenyl)-6,7-dimethoxyisoquinoline-1-methanol;papaverinol;α-(3,4-Dimethoxyphenyl)-6,7-dimethoxy-1-isoquinolinemethanol;(6,7-dimethoxy-1-isoquinolyl)-(3,4-dimethoxyphenyl)methanol;(6,7-dimethoxyisoquinolin-1-yl)-(3,4-dimethoxyphenyl)methanol
• CAS NO: 482-76-8
• Molecular Formula: C₂₀H₂₁NO₅
• Molecular Weight: 355.38444
• EINECS: 207-585-3
• Mol File: 482-76-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 138-139 °C
• Boiling Point: 534.6°Cat760mmHg
• Flash Point: 277.1°C
• Appearance: /
• Density: 1.223g/cm³
• PKA: 12.15±0.20(Predicted)
• CAS DataBase Reference: alpha-(3,4-dimethoxyphenyl)-6,7-dimethoxyisoquinoline-1-methanol(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-(3,4-dimethoxyphenyl)-6,7-dimethoxyisoquinoline-1-methanol(482-76-8)
• EPA Substance Registry System: alpha-(3,4-dimethoxyphenyl)-6,7-dimethoxyisoquinoline-1-methanol(482-76-8)

Safety Data

• Hazardous Substances Data: 482-76-8(Hazardous Substances Data)

Upstream product

• 58-74-2 Papaverine 
• 1600-27-7 mercury(II) diacetate 
• 64-19-7 acetic acid 
• 522-57-6 papaveraldine 
• 102311-65-9 (+/-)-2-trans-cinnamoyl-6,7-dimethoxy-1,2-dihydro-isoquinoline-1-carbonitrile 
• 61-25-6 papaverine hydrochloride 
• 7664-93-9 sulfuric acid 
• 7732-18-5 water 
• 15248-39-2 6,7-dimethoxyisoquinoline 
• 3382-18-1 6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 58163-19-2 dimethoxy-3,4 benzylideneaminoacetal diethylique 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 

Downstream Products

• 26805-24-3 benzoyloxy-(6,7-dimethoxy-isoquinolin-1-yl)-(3,4-dimethoxy-phenyl)-methane 
• 58-74-2 Papaverine 
• 522-57-6 papaveraldine 
• 180386-76-9 (±)-1-[(3,4-dimethoxyphenyl)(methoxy)methyl]-6,7-dimethoxyisoquinoline 

Relevant articles and documents

Oxidation and degradation products of papaverine. Part I: Gadamer and Schulemann's papaverinol synthesis revisited

In 1915 Gadamer published in this journal [1] a procedure for the synthesis of papaverinol 2 from papaverine 1 in excellent yield. However, he did not investigate the formation of a violet fluorescence produced upon crystallization of papaverinol 2 from ethanol. The compound responsible for this fluorescence was isolated and identified as the yet unknown quaternary ammonium ion 4, a 6a, 12a-diazadibenzo[a,g]fluorenylium derivative. The isolation of 4 and its structure determination by spectroscopic methods are described. However, its formation mechanism is unknown.

Preparation method of papaverine compounds

The invention relates to a preparation method of papaverine compounds. Specifically, the invention relates to a preparation method of a compound as shown in a formula II, and the preparation method comprises a step of reacting a compound as shown in a formula III in the presence of an oxidizing agent. The method is high in yield, mild in reaction condition and suitable for industrial production.

A divergent approach to benzylisoquinoline-type and oxoaporphine alkaloids via regioselective direct ring metalation of alkoxy isoquinolines

Methoxy- and benzyloxy-substituted isoquinolines are regioselectively metalated at C-1 with the Knochel-Hauser base, subsequent trapping with aromatic aldehydes gives aryl(isoquinolin-1-yl)carbinols as building blocks for divergent syntheses of different types of benzylisoquinoline alkaloids. Photochemical cyclization of ortho-bromo analogues under reductive conditions gives oxoaporphine alkaloids. Nine benzylisoquinoline alkaloids and two oxoaporphine alkaloids were obtained in two or three steps from appropriate isoquinolines.