475-81-0

Basic information

• Product Name: BOLDINE DIMETHYL ETHER
• Synonyms: bromcholitin;d-glaucine;glauvent;(+)-GLAUCINE;GLAUCINE;BOLDINE DIMETHYL ETHER;1,2,9,10-TETRAMETHOXYAPORPHINE;(S)-1,2,9,10-TETRAMETHOXY-6-METHYL-5,6,6A,7-TETRAHYDRO-4H-DIBENZO[DE,G]QUINOLINE
• CAS NO: 475-81-0
• Molecular Formula: C₂₁H₂₅NO₄
• Molecular Weight: 355.43
• EINECS: 207-501-5
• Product Categories: Heterocycles
• Mol File: 475-81-0.mol
• Article Data: 15

Chemical Properties

• Melting Point: 246-247℃
• Boiling Point: 488.45°C (rough estimate)
• Flash Point: 140.2°C
• Appearance: /
• Density: 1.166±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 1.23E-09mmHg at 25°C
• Refractive Index: 1.5614 (estimate)
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 6.35±0.20(Predicted)
• CAS DataBase Reference: BOLDINE DIMETHYL ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: BOLDINE DIMETHYL ETHER(475-81-0)
• EPA Substance Registry System: BOLDINE DIMETHYL ETHER(475-81-0)

Safety Data

• Hazardous Substances Data: 475-81-0(Hazardous Substances Data)

Usage

Description

Glaucine (Item No. 17338) is an analytical reference standard categorized as an antitussive. Glaucine has hallucinogenic properties. This product is intended for research and forensic applications.

Uses

d-Glaucine has bronchodilator and antiinflammatory effects, acting as a PDE4 inhibitor and calcium channel blocker, and is used medically as an antitussive in some countries.

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/t15-/m0/s1

Upstream product

• 5630-11-5 (+/-)-glaucine 
• 186581-53-3 diazomethane 
• 1336-21-6 ammonium hydroxide 
• 7732-18-5 water 
• 76-05-1 trifluoroacetic acid 
• 407-25-0 trifluoroacetic anhydride 
• 1699-51-0 laudanosine 
• 5890-18-6 (+)-norboldine 
• 371196-16-6 (6aS)-4,5,6a,7-tetrahydro-1,2,9,10-tetramethoxy-6H-dibenzo[de,g]quinoline-6-carbaldehyde 
• 85-63-2 (R)-laudanosine 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 1198362-82-1 (S)-methyl 1,2,9,10-tetramethoxy-6a,7-dihydro-4H-dibenzo[de,g]quinoline-6(5H)-carboxylate 
• 4230-93-7 3,4-dimethoxynitrostyrene 
• 41823-67-0 1-(2'-bromo-4',5'-dimethoxybenzyl)-6,7-dimethoxy-3,4-dihydroisoquinoline 

Downstream Products

• 20068-96-6 (+)-thalicmidine 
• 72498-23-8 glaucine N-oxide 
• 3019-51-0 isoboldine 
• 25651-04-1 bracteoline 
• 1418137-71-9 11-sulfonyl-1,11-anhydrobracteoline 
• 5083-88-5 thaliporphine 
• 21848-62-4 1,2,9,10-tetramethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline 

Relevant articles and documents

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Enantioselective synthesis and anti-parasitic properties of aporphine natural products

Chagas disease and visceral leishmaniasis are neglected protozoan diseases with significant impact in developing countries. Due to the limited number and toxicity of current therapies, new drug leads are urgently needed. In this work, four aporphine natural products were synthesized using an enantioselective, modular and convergent strategy, comprising eight steps in the longest linear sequence; key steps included Bischler-Napieralski cyclization/Noyori asymmetric reduction to construct the tetrahydroisoquinolines, and palladium-catalyzed arylation to close the C ring. Norglaucine, nordicentrine and dicentrine showed promising bioactivity against T. cruzi and L. infantum, suggesting potential for further development of these scaffolds as antiparasitic agents.

Semisynthesis and myocardial activity of thaliporphine N-homologues

The N-homologues and optical isomers of thaliporphine (5a), a potent antiarrhythmic agent, were prepared starting from laurolitsine (1), an abundant aporphine present in Phoebe formosana. Treating N-propylnorglaucine with 90% H2SO4 yielded one additional product, an 11-sulfonyl-1,11-anhydroaporphine. Reaction of N-formylnorglaucine (3a) with 90% H2SO4, however, yielded the 9-sulfonyl-seco product as a major product. Treatment of 3a with 98% H2SO4 yielded pancordine (10), which, upon catalytic hydrogenation, yielded (±)-wilsonirine. 1H NMR spectroscopic analysis was applied successfully to monitor the optical purity of the crystalline salt while undertaking optical resolution. Thaliporphine (5a) was demonstrated to possess better positive inotropic and less negative chronotropic effects than the left-hand optical isomer and showed the best activity on rat cardiac tissue among the N-homologues prepared.