Glaucine

Base Information

• Chemical Name: Glaucine
• CAS No.: 475-81-0
• Molecular Formula: C21H25 N O4
• Molecular Weight: 355.434
• Hs Code.: 2933990090
• European Community (EC) Number: 207-501-5
• NSC Number: 34396
• UNII: NU19306XA7
• DSSTox Substance ID: DTXSID8031100
• Nikkaji Number: J12.036G
• Wikipedia: Glaucine
• Wikidata: Q2398298
• Pharos Ligand ID: MXB23HQ4F9J3
• Metabolomics Workbench ID: 67658
• ChEMBL ID: CHEMBL228082
• Mol file: 475-81-0.mol

Synonyms:glaucine;glaucine acetate, (+-)-isomer;glaucine citrate, (+-)-isomer;glaucine hydrobromide, (+-)-isomer;glaucine hydrobromide, (R)-isomer;glaucine hydrobromide, (S)-isomer;glaucine hydrochloride, (+-)-isomer;glaucine hydrochloride, (R)-isomer;glaucine hydrochloride, (S)-isomer;glaucine hydroiodide, (R)-isomer;glaucine hydroiodide, (S)-isomer;glaucine maleate, (+-)-isomer;glaucine mesylate, (+-)-isomer;glaucine phosphate;glaucine phosphate (2:3), (+-)-isomer;glaucine phosphate (2:3), (R)-isomer;glaucine phosphate (2:3), (S)-isomer;glaucine phosphate (5:7), (+-)-isomer;glaucine phosphate (5:8), (+-)-isomer;glaucine phosphate, (S)-isomer;glaucine sulphate, (+-)-isomer;glaucine tartrate (1:1), (+-)-isomer;glaucine tartrate (1:1), (R)-isomer;glaucine tartrate (1:1), (S)-isomer;glaucine tartrate, (+-)-isomer;glaucine tartrate, (R)-isomer;glaucine tartrate, (S)-isomer;glaucine tosylate, (R)-isomer;glaucine, (R)-isomer;glaucine, (S)-isomer;tussiglaucin

Chemical Property of Glaucine

Chemical Property:

• Vapor Pressure: 1.23E-09mmHg at 25°C
• Melting Point: 246-247oC
• Refractive Index: 1.5614 (estimate)
• Boiling Point: 487°Cat760mmHg
• PKA: 6.35±0.20(Predicted)
• Flash Point: 140.2°C
• PSA: 40.16000
• Density: 1.166g/cm³
• LogP: 3.41100
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 355.17835828
• Heavy Atom Count: 26
• Complexity: 489

Purity/Quality:

99%, ^*data from raw suppliers

d-Glaucine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C(C3=C2C1CC4=CC(=C(C=C43)OC)OC)OC)OC
• Isomeric SMILES: CN1CCC2=CC(=C(C3=C2[C@@H]1CC4=CC(=C(C=C43)OC)OC)OC)OC
• 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.

Technology Process of Glaucine

There total 32 articles about Glaucine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

ammonium hydroxide (1336-21-6) + hydrated ruthenium oxide + water (7732-18-5) + trifluoroacetic acid (76-05-1) + trifluoroacetic anhydride (407-25-0) + laudanosine (1699-51-0,20412-65-1) → glaucine (475-81-0)

Guidance literature:

With BF₃ etherate; In dichloromethane;

Reference yield: 87.0%

phenyltrimethylammonium chloride (138-24-9) + boldine (476-70-0) → glaucine (475-81-0)

Guidance literature:

With potassium tert-butylate; In N,N-dimethyl-formamide; at 90 ℃; for 16h;

DOI:10.1081/SCC-120014988

Reference yield: 84.0%

(6aS)-4,5,6a,7-tetrahydro-1,2,9,10-tetramethoxy-6H-dibenzo[de,g]quinoline-6-carbaldehyde (371196-16-6) → glaucine (475-81-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere; Reflux;

DOI:10.1021/np3007765

upstream raw materials:

(+/-)-glaucine

(S)-laudanosine

diazomethane

phenyltrimethylammonium chloride

Downstream raw materials:

(+)-thalicmidine

glaucine N-oxide

isoboldine

bracteoline

Refernces

Aporphine synthesis by Pschorr cyclization of aminophenols. An improved synthesis of a thalicarpine precursor.

10.1021/jo00942a048

The research presents an improved general synthesis of aporphines via Pschorr cyclization of 1-(2’-aminobenzyl)-7-hydroxy-l,2,3,4-tetrahydroisoquinolines. The key chemicals involved in this research include o-nitrotoluenes (2a-e), 6-methoxy-7-hydroxy-3,4-dihydroisoquinolinium methiodide, KO-t-Bu, Pd/C, Zn-H2SO4, diazomethane, and copper powder. The synthesis involves several steps: condensation of o-nitrotoluenes with 6-methoxy-7-hydroxy-3,4-dihydroisoquinolinium methiodide in the presence of KO-t-Bu to form 1-(2’-nitrobenzyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinolines (3a-e); reduction of these compounds with Pd/C or Zn-H2SO4 to obtain aminophenols (4a-f); and cyclization of the aminophenols to form 1-hydroxyaporphines (5a-f) using diazotization and copper powder. The final products include thalicmidine (5g), nuciferine (6a), glaucine (6g), and the thalicarpine precursor 6e. The synthesis is notable for achieving the highest yields reported to date for these compounds.

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