28832-07-7

Basic information

• Product Name: L-DICENTRINE
• Synonyms: (R)-(-)-DICENTRINE;L-DICENTRINE;(7aR)-6,7,7a,8-Tetrahydro-10,11-dimethoxy-7-methyl-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline;Cepharanthine α-base;Eximine;10,11-Dimethoxy-7-methyl-6,7,7A,8-tetrahydro-5H-benzo[G][1,3]benzodioxolo[6,5,4-de]quinoline;5H-Benzo[G]-1,3-benzodioxolo[6,5,4-de]quinoline, 6,7,7A,8-tetrahydro-10,11-dimethoxy-7-methyl-;Inchi=1/C20H21no4/C1-21-5-4-11-7-17-20(25-10-24-17)19-13-9-16(23-3)15(22-2)8-12(13)6-14(21)18(11)19/H7-9,14H,4-6,10H2,1-3h
• CAS NO: 28832-07-7
• Molecular Formula: C₂₀H₂₁NO₄
• Molecular Weight: 339.39
• Product Categories: Heterocycles;Aromatics;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 28832-07-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 480.7°Cat760mmHg
• Flash Point: 142.7°C
• Appearance: /
• Density: 1.266±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 2.12E-09mmHg at 25°C
• Refractive Index: 1.615
• PKA: 6.65±0.20(Predicted)
• CAS DataBase Reference: L-DICENTRINE(CAS DataBase Reference)
• NIST Chemistry Reference: L-DICENTRINE(28832-07-7)
• EPA Substance Registry System: L-DICENTRINE(28832-07-7)

Safety Data

• Hazardous Substances Data: 28832-07-7(Hazardous Substances Data)

Usage

Uses

A natural vascular alpha 1-adrenoceptor antagonist but less prevalent than the D-isomer. It markedly inhibits the contraction of rat stomach muscle strips induced by 5-HT, histamine, K+ and Ca2+ after high K+ depolarization, showing a non-competitive antagonism and could be a potential muscle relaxant. Studies suggest that it has protective effect of on acute myocardial Iichemia and anoxia lesion.

InChI:InChI=1/C20H21NO4/c1-21-5-4-11-7-17-20(25-10-24-17)19-13-9-16(23-3)15(22-2)8-12(13)6-14(21)18(11)19/h7-9,14H,4-6,10H2,1-3H3/t14-/m1/s1

Upstream product

• 25368-02-9 (-)-phanostenine 

Relevant articles and documents

In vitro functional evaluation of isolaureline, dicentrine and glaucine enantiomers at 5-HT2 and α1 receptors

Compounds with activity at serotonin (5-hydroxytryptamine) 5-HT2 and α1 adrenergic receptors have potential for the treatment of central nervous system disorders, drug addiction or overdose. Isolaureline, dicentrine and glaucine enantiomers were synthesized, and their in vitro functional activities at human 5-HT2 and adrenergic α1 receptor subtypes were evaluated. The enantiomers of isolaureline and dicentrine acted as antagonists at 5-HT2 and α1 receptors with (R)-isolaureline showing the greatest potency (pKb?=?8.14 at the 5-HT2C receptor). Both (R)- and (S)-glaucine also antagonized α1 receptors, but they behaved very differently to the other compounds at 5-HT2 receptors: (S)-glaucine acted as a partial agonist at all three 5-HT2 receptor subtypes, whereas (R)-glaucine appeared to act as a positive allosteric modulator at the 5-HT2A receptor.