Lysicamine

Base Information

• Chemical Name: Lysicamine
• CAS No.: 15444-20-9
• Molecular Formula: C18H13 N O3
• Molecular Weight: 291.3
• Hs Code.: 2933990090
• NSC Number: 628003
• UNII: 6L30DD6R7O
• DSSTox Substance ID: DTXSID00165628
• Nikkaji Number: J14.079A
• Wikidata: Q27138982
• Metabolomics Workbench ID: 140860
• ChEMBL ID: CHEMBL510090
• Mol file: 15444-20-9.mol

Synonyms:1,2-dimethoxy-7H-dibenzo(de,g)quinolin-7-one;lysicamine;oxonuciferine

Chemical Property of Lysicamine

Chemical Property:

• Vapor Pressure: 1.71E-10mmHg at 25°C
• Boiling Point: 509.4°Cat760mmHg
• Flash Point: 261.9°C
• PSA: 48.42000
• Density: 1.323g/cm³
• LogP: 3.46340
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 291.08954328
• Heavy Atom Count: 22
• Complexity: 440

Purity/Quality:

99% ^*data from raw suppliers

Lysicamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C2=C3C(=C1)C=CN=C3C(=O)C4=CC=CC=C42)OC
• General Description: Lysicamine is an aporphinoid alkaloid synthesized via an efficient and selective intermolecular benzyne cycloaddition (IBC) approach, which enables the construction of its core structure without ring-D substituents. This method highlights its potential as a pharmacologically relevant compound within the broader class of isoquinoline alkaloids.

Technology Process of Lysicamine

There total 3 articles about Lysicamine 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: 57.0%

(±)-(2-bromophenyl)(6,7-dimethoxyisoquinolin-1-yl)methanol (260552-69-0) → lysicamine (15444-20-9) + 1-[(phenyl)hydroxymethyl]-6,7-dimethoxyisoquinoline (22190-47-2)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 4h; Heating;

DOI:10.1021/ol990360v

Reference yield: 45.0%

(2-Bromo-phenyl)-(6,7-dimethoxy-isoquinolin-1-yl)-methanone (193551-54-1) → lysicamine (15444-20-9) + 1-[(phenyl)hydroxymethyl]-6,7-dimethoxyisoquinoline (22190-47-2) + (±)-(2-bromophenyl)(6,7-dimethoxyisoquinolin-1-yl)methanol (260552-69-0)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 4h; Heating;

DOI:10.1021/ol990360v

Reference yield: 40.0%

(2-bromo-phenyl)-(6,7-dimethoxy-3,4-dihydro-[1]isoquinolyl)-ketone (260552-68-9) → lysicamine (15444-20-9) + (6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)(phenyl)methanone (22190-45-0)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 4h; Heating;

DOI:10.1021/ol990360v

upstream raw materials:

(2-bromo-phenyl)-(6,7-dimethoxy-3,4-dihydro-[1]isoquinolyl)-ketone

(2-Bromo-phenyl)-(6,7-dimethoxy-isoquinolin-1-yl)-methanone

(±)-(2-bromophenyl)(6,7-dimethoxyisoquinolin-1-yl)methanol

Refernces

Intermolecular Benzyne Cycloaddition Approach to Aporphinoids. Total Syntheses of Norcepharadione B, Cepharadione B, Dehydroanonaine, Duguenaine, Dehydronornuciferine, Pontevedrine, O-Methylatheroline, Lysicamine, and Alkaloid PO-3

10.1021/jo00009a010

The research focuses on the development of a novel approach to the synthesis of aporphinoids, a class of isoquinoline alkaloids with potential pharmacological properties. The purpose of the study was to create a more efficient method for synthesizing these complex compounds, particularly dehydroaporphines, aristolactams, and other related structures, through intermolecular benzyne cycloaddition (IBC). The researchers successfully reported the total synthesis of several isoquinoline alkaloids, including norcepharadione B, cepharadione B, dehydroanonaine, duguenaine, dehydronornuciferine, pontevedrine, 0-methylatheroline, lysicamine, and alkaloid PO-3. The study concluded that the IBC approach was highly selective and efficient, allowing for the synthesis of aporphinoids with no ring-D substituents in yields of up to 50%. Key chemicals used in the process included 1-methyleneisoquinolines, arynes, and various benzenediazonium-2-carboxylates, which served as benzyne precursors in the cycloaddition reactions. The research also explored the synthesis of aporphinoids with ring-D substituents using alkoxy-substituted benzynes and unsymmetrically substituted benzynes, demonstrating the versatility of the IBC method.