517-65-7

Usage

Uses

Used in Pharmaceutical Industry:
(6aS)-5,6,6a,7-Tetrahydro-1,9,10-trimethoxy-6-methyl-4H-dibenzo[de,g]quinolin-2-ol is used as a pharmaceutical compound for its potential therapeutic applications. As an alkaloid, it may possess bioactive properties that can be harnessed for the development of new drugs or treatments.
Used in Chemical Research:
(6aS)-5,6,6a,7-Tetrahydro-1,9,10-trimethoxy-6-methyl-4H-dibenzo[de,g]quinolin-2-ol is also used in chemical research, particularly in the study of aporphine alkaloids and their potential applications. Researchers may utilize (6aS)-5,6,6a,7-Tetrahydro-1,9,10-trimethoxy-6-methyl-4H-dibenzo[de,g]quinolin-2-ol to better understand the structure-activity relationships of aporphine alkaloids and to develop new synthetic methods for their preparation.
Used in Natural Product Extraction:
(6aS)-5,6,6a,7-Tetrahydro-1,9,10-trimethoxy-6-methyl-4H-dibenzo[de,g]quinolin-2-ol can be used in the extraction and purification processes of natural products from plants, such as Ocotea macropoda. (6aS)-5,6,6a,7-Tetrahydro-1,9,10-trimethoxy-6-methyl-4H-dibenzo[de,g]quinolin-2-ol may serve as a marker or indicator for the presence of bioactive compounds in plant extracts, aiding in the identification and quantification of these substances.

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

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

Relevant academic research and scientific papers

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

Antihyperglycemic effect of aporphines and their derivatives in normal and diabetic rats

The antihyperglycemic actions of some aporphines and their derivatives in normal Wistar, streptozotocin (STZ)-induced diabetic (IDDM) and nicotinamide-STZ induced diabetic (NIDDM) rats were investigated in this study. These compounds included thaliporphine, glaucine, boldine, N-methyllaurotetanine, and predicentrine and the derivatives, N-[2-(2-methoxyphenoxy)ethyl]-norglaucine and diacetyl-N-allylsecoboldine. Bolus intravenous injection of these compounds decreased the plasma glucose levels in a dose-dependent manner in both normal and diabetic rats. Among them, thaliporphine was found to have the most potent antihyperglycemic effect in both NIDDM and IDDM diabetic rats. It was found that thaliporphine could stimulate the release of insulin in both normal and diabetic rats, and a dose of 1 mg per kg thaliporphine could significantly attenuate the increase of plasma glucose induced by an intravenous glucose challenge test in normal rats. Similar treatment with thaliporphine significantly increased the skeletal muscle glycogen synthesis in both normal and diabetic rats. Hence, the hypoglycemic effect of thaliporphine in diabetic rats could be attributed to the stimulation of insulin release and the increase of glucose utilization. Georg Thieme Verlag KG Stuttgart.

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.