524-20-9

Basic information

• Product Name: ARMEPAVINE
• Synonyms: (-)-Armepavine; (R)-(-)-Armepavine; 4-(6,7-Dimethoxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-ylmethyl)-phenol; 4-[(6,7-Dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]phenol; 524-20-9; Armepavine (8CI); Evoeuropine; Phenol, 4-((1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl)-; Phenol, 4-((1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl)-, (+-)-; armepavine
• CAS NO: 524-20-9
• Molecular Formula: C₁₉H₂₃NO₃
• Molecular Weight: 313.39082
• Product Categories: Alkaloids
• Mol File: 524-20-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 149-150°
• Boiling Point: 460.5°Cat760mmHg
• Flash Point: 232.3°C
• Appearance: /
• Density: 1.151g/cm³
• Vapor Pressure: 4.21E-09mmHg at 25°C
• Refractive Index: 1.584
• PKA: 9.99±0.15(Predicted)
• CAS DataBase Reference: ARMEPAVINE(CAS DataBase Reference)
• NIST Chemistry Reference: ARMEPAVINE(524-20-9)
• EPA Substance Registry System: ARMEPAVINE(524-20-9)

Safety Data

• Hazardous Substances Data: 524-20-9(Hazardous Substances Data)

Usage

General Description

ArMEPAVINE is a naturally occurring chemical compound commonly found in plants of the Papaveraceae family, such as the greater celandine, Prickly Poppy, and Corydalis yanhusuo. It is classified as an isoquinoline alkaloid and is known for its potential medicinal properties. Experimental studies suggest that ArMEPAVINE may have potential antiproliferative and apoptotic effects on cancer cells, neuroprotective capabilities, anti-inflammatory effects, and antinociceptive activities. However, further research is required to fully understand its properties and potential therapeutic applications.

InChI:InChI=1/C19H23NO3/c1-20-9-8-14-11-18(22-2)19(23-3)12-16(14)17(20)10-13-4-6-15(21)7-5-13/h4-7,11-12,17,21H,8-10H2,1-3H3

Upstream product

• 1246431-54-8 C₁₈H₁₅Cl₃O₆ 
• 1580442-44-9 methyl 2-{4-hydroxy-3-[4-(2-methoxy-2-oxoethyl)phenoxy]phenyl}acetate 
• 42583-41-5 2-{4-[5-(carboxymethyl)-2-methoxyphenoxy]phenyl}acetic acid 
• 409366-27-4 (3,5-dichloro-4-hydroxyphenyl)acetic acid methyl ester 
• 228271-22-5 6,7-dimethoxy-1-[[4-[5-(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolinyl)methyl-2-methoxy]phenoxy]benzyl]-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 14199-15-6 Methyl 4-hydroxyphenylacetate 
• 1580442-46-1 C₅₃H₅₈N₂O₈ 
• 1246431-52-6 C₁₉H₁₇Cl₃O₇ 
• 50-00-0 formaldehyd 
• 477-62-3 (R,R)-isochondodendrine 
• 6392-40-1 N-Norarmepavine 
• 518-94-5 (-)-cycleanine 
• 30745-31-4 cycleanine 

Downstream Products

• 36417-79-5 2-methylisococlaurine 
• 5701-00-8 (R)-O-methylarmepavine 

Relevant articles and documents

Organocatalytic Enantioselective Pictet-Spengler Approach to Biologically Relevant 1-Benzyl-1,2,3,4-Tetrahydroisoquinoline Alkaloids

(Figure Presented) A general procedure for the synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines was developed, based on organocatalytic, regio- and enantioselective Pictet-Spengler reactions (86-92% ee) of N-(o-nitrophenylsulfenyl)-2-arylethylamines with arylacetaldehydes. The presence of the o-nitrophenylsulfenyl group, together with the MOM-protection in the catechol part of the tetrahydroisoquinoline ring system, appeared to be a productive combination. To demonstrate the versatility of this approach, 10 biologically and pharmaceutically relevant alkaloids were prepared using (R)-TRIP as the chiral catalyst: (R)-norcoclaurine, (R)-coclaurine, (R)-norreticuline, (R)-reticuline, (R)-trimemetoquinol, (R)-armepavine, (R)-norprotosinomenine, (R)-protosinomenine, (R)-laudanosine, and (R)-5-methoxylaudanosine.

Effect of isoquinoline alkaloids of different structural types on antiplatelet aggregation in vitro

Forty-one isoquinoline alkaloids were tested for antiplatelet aggregation effects. Among them, (-)-discretamine (6), protopine (7), ochotensimine (18), O-methylarmepavinemethine (23), lindoldhamine (25), isotetrandrine (26), thalicarpine (27), papaverine (28), and D-(+)-N-norarmepavine (32) exhibited significant inhibitory activity towards adenosine 5′-diphosphate (ADP)-, arachidonic acid (AA)-, collagen-, and/or platelet-activating factor (PAF)-induced platelet aggregation. The results are discussed on the basis of structure-activity relationships. Georg Thieme Verlag KG Stuttgart.