517-65-7

Basic information

• Product Name: (6aS)-5,6,6a,7-Tetrahydro-1,9,10-trimethoxy-6-methyl-4H-dibenzo[de,g]quinolin-2-ol
• Synonyms: (6aS)-5,6,6a,7-Tetrahydro-1,9,10-trimethoxy-6-methyl-4H-dibenzo[de,g]quinolin-2-ol;Predicentrine
• CAS NO: 517-65-7
• Molecular Formula: C₂₀H₂₃NO₄
• Molecular Weight: 341.4009
• Mol File: 517-65-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 505.7°Cat760mmHg
• Flash Point: 259.7°C
• Appearance: /
• Density: 1.222g/cm³
• Vapor Pressure: 7.51E-11mmHg at 25°C
• Refractive Index: 1.603
• CAS DataBase Reference: (6aS)-5,6,6a,7-Tetrahydro-1,9,10-trimethoxy-6-methyl-4H-dibenzo[de,g]quinolin-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (6aS)-5,6,6a,7-Tetrahydro-1,9,10-trimethoxy-6-methyl-4H-dibenzo[de,g]quinolin-2-ol(517-65-7)
• EPA Substance Registry System: (6aS)-5,6,6a,7-Tetrahydro-1,9,10-trimethoxy-6-methyl-4H-dibenzo[de,g]quinolin-2-ol(517-65-7)

Safety Data

• Hazardous Substances Data: 517-65-7(Hazardous Substances Data)

Usage

Description

An alkaloid of the aporphine class, the base occurs in Ocotea macropoda. The structure has been established by synthesis of the optically inactive form using 4-methoxy-3-benzyloxyphenylethylamine as the starting material.

References

Charubulaetal., Chem. Ber., 101,2665 (1968)

InChI:InChI=1/C20H23NO4/c1-21-6-5-11-8-15(22)20(25-4)19-13-10-17(24-3)16(23-2)9-12(13)7-14(21)18(11)19/h8-10,14,22H,5-7H2,1-4H3

Upstream product

• 186581-53-3 diazomethane 
• 476-70-0 boldine 
• 98-04-4 phenyltrimethylammonium iodide 
• 67-56-1 methanol 

Relevant articles and documents

Semisynthetic studies on and biological evaluation of N-methyllaurotetanine analogues as ligands for 5-HT receptors

N-Methyllaurotetanine (1) has been reported to display good affinity for the 5-HT1A receptor, but no structure-affinity studies have been performed to date. The commercially available alkaloid boldine (2) was used as the starting material for s

Structure-affinity relationships of halogenated predicentrine and glaucine derivatives at D1 and D2 dopaminergic receptors: Halogenation and D1 receptor selectivity

Halogenation of the aporphine alkaloid boldine at the 3-position leads to increased affinity for rat brain D1-like dopaminergic receptors with some selectivity over D2-like receptors. A series of 3-halogenated and 3,8-dihalogenated (halogen = Cl, Br or I) derivatives of predicentrine (9-O-methylboldine) and glaucine (2,9-di-O-methylboldine) were prepared and assayed for binding at D1 and D2 sites. Halogenation of predicentrine led to strong increases in affinity for D1-like receptors, while the affinities for D2-like receptors were either practically unchanged or reduced three- to fourfold. Halogenated glaucine derivatives did not show any clear trend towards enhanced selectivity, and the affinities were poor and similar to or worse than the values previously recorded for glaucine itself. Together with earlier work on boldine derivatives, these results suggest that the 2-hydroxy group on the aporphine skeleton may determine a binding mode favoring D1-like over D2-like receptors, with enhanced affinity when the C-3 position is halogenated.