5630-11-5

Basic information

• Product Name: glaucine
• Synonyms: (+/-)-O,O-Dimethylboldine;(+/-)-O,O-Dimethylisoboldine;1,2,9,10-Tetramethoxy-6-methylnoraporphine;2,3,5,6-Tetramethoxyaporphine;DL-1,2,9,10-Tetramethoxyaporphine;DL-Glaucine
• CAS NO: 5630-11-5
• Molecular Formula: C₂₁H₂₅NO₄
• Molecular Weight: 355.4275
• EINECS: 227-068-6
• Mol File: 5630-11-5.mol
• Article Data: 26

Chemical Properties

• Melting Point: 119℃
• Boiling Point: 487°Cat760mmHg
• Flash Point: 140.2°C
• Appearance: /
• Density: 1.166
• Vapor Pressure: 1.23E-09mmHg at 25°C
• Refractive Index: 1.575
• CAS DataBase Reference: glaucine(CAS DataBase Reference)
• NIST Chemistry Reference: glaucine(5630-11-5)
• EPA Substance Registry System: glaucine(5630-11-5)

Safety Data

• Hazardous Substances Data: 5630-11-5(Hazardous Substances Data)

Usage

General Description

Glaucine is a naturally occurring alkaloid found in several plant species, most notably in the yellow hornpoppy and in the seeds of the Glaucium flavum plant. It has been used traditionally in Chinese medicine for its anti-inflammatory and analgesic properties. Glaucine has also shown potential as a treatment for respiratory conditions such as asthma and chronic obstructive pulmonary disease (COPD) due to its bronchodilator effects. Additionally, it has been studied for its potential in weight loss and cancer treatment. Glaucine is known to act as a dopamine receptor antagonist and as a calcium channel blocker, which may contribute to its therapeutic effects. However, more research is needed to fully understand its mechanisms of action and potential applications.

InChI:InChI=1/C21H25NO4/c1-22-7-6-12-9-18(25-4)21(26-5)20-14-11-17(24-3)16(23-2)10-13(14)8-15(22)19(12)20/h9-11,15H,6-8H2,1-5H3

Upstream product

• 1699-51-0 laudanosine 
• 16620-96-5 2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 38973-42-1 6,7-dimethoxy-2-methylisoquinoline-1,3(2H,4H)-dione 
• 3809-00-5 4,5-dimethoxyhomophthalic acid 
• 134619-96-8 C₁₂H₁₇BF₃NO₂ 
• 7630-72-0 (+/-)-N-ethoxycarbonyldehydronorglaucine 
• 39945-38-5 4H-1,2,9,10-tetramethoxy-5,6-dihydrodibenzo[de,g]quinoline 
• 149110-86-1 9,9-bis(ethylthio)-5,6,6a,7,7a,8,9,10-octahydro-1,2-dimethoxy-6-methyl-4H-dibenzoquinolin-10-one 
• 149110-86-1 9,9-bis(ethylthio)-5,6,6a,7,7a,8,9,10-octahydro-1,2-dimethoxy-6-methyl-4H-dibenzoquinolin-10-one 
• 149110-85-0 1,2,3,8,9,9a-hexahydro-5,6-dimethoxy-1-methyl-8-<(dimethylamino)methyl>-7H-benzoquinolin-7-one 
• 35690-87-0 1,2,3,8,9,9a-hexahydro-5,6-dimethoxy-1-methyl-7H-benzoquinolin-7-one 
• 80941-67-9 7-Formyldehydroglaucine 
• 80955-23-3 7-Hydroxymethyldehydroglaucine 
• 22212-26-6 dehydroglaucine 

Downstream Products

• 475-81-0 glaucine 
• 475-81-0 (-)-(R)-glaucine 
• 22212-26-6 dehydroglaucine 
• 5574-24-3 oxoglaucine 
• 34647-65-9 pontevedrine 
• 103769-59-1 corrunine 
• 28230-74-2 2,9-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-1,10-diol 
• 2755-00-2 thaliporphine 
• 82644-87-9 7-(p-Methoxy-phenoxy)-dehydroglaucin 
• 82644-89-1 7-(2,5-Dihydroxy-phenyl)-dehydroglaucin 
• 82644-88-0 7-(p-Hydroxy-phenoxy)-dehydroglaucin 

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.

Application of the hypervalent iodine reagent to the synthesis of some pentasubstituted aporphine alkaloids

The oxidative biaryl coupling of various N-substituted 1- benzyltetrahydroisoquinolines to the corresponding aporphines by the hypervalent iodine reagent was studied. The study sheds light on the unifying mechanism of the reaction illustrating the requirement of the p-p coupling via the six-membered transition state as the initial step. The finding was applied to the synthesis of some pentasubstituted aporphine alkaloids. Georg Thieme Verlag Stuttgart.

Synthesis of (±)-Glaucine and (±)-Neospirodienone via an One-Pot Bischler-Napieralski Reaction and Oxidative Coupling by a Hypervalent Iodine Reagent

Condensation of 3,4-dimethoxybenzeneethanamine (3d) and various benzeneacetic acids, i.e., 4a-e, via a practical and efficient one-pot Bischler-Napieralski reaction, followed by NaBH4 reduction, produced a series of 1-benzyl-1,2,3,4-tetrahydroisoquinolines, i.e., 5a-e, in satisfactory yields (Scheme 3). Oxidative coupling of the N-acyl and N-methyl derivatives 6a-e of the latter with hypervalent iodine ([IPh(CF 3COO)2]) yielded products with two different skeletons (Scheme 4). The major products from N-acyl derivatives 6a-c were (±)-N-acylneospirodienones 2a-c, while the minor was the 3,4-dihydroisoquinoline 7. (±)-Glaucine (1), however, was the major product starting from N-methyl derivative 6e. Possible reaction mechanisms for the formation of these two types of skeleton are proposed (Scheme 5).