15444-20-9

Basic information

• Product Name: Lysicamine
• Synonyms: Lysicamine;1,2-Dimethoxy-7H-dibenzo[de,g]quinolin-7-one;Oxonuciferine
• CAS NO: 15444-20-9
• Molecular Formula: C₁₈H₁₃NO₃
• Molecular Weight: 291.305
• Mol File: 15444-20-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 509.4°Cat760mmHg
• Flash Point: 261.9°C
• Appearance: /
• Density: 1.323g/cm³
• Vapor Pressure: 1.71E-10mmHg at 25°C
• Refractive Index: 1.68
• CAS DataBase Reference: Lysicamine(CAS DataBase Reference)
• NIST Chemistry Reference: Lysicamine(15444-20-9)
• EPA Substance Registry System: Lysicamine(15444-20-9)

Safety Data

• Hazardous Substances Data: 15444-20-9(Hazardous Substances Data)

Usage

Description

Lysicamine is an oxodibenzoquinoline alkaloid that can be found in Lysichiton camtschatcense Schott var. japonicum Makino. This fully conjugated molecule is colored and forms yellow needles when crystallized from ethanol. It exhibits unique absorption maxima in both neutral and acid solutions, and its structure has been confirmed through synthesis as 1:2-dimethoxy-7-oxodibenzo[de,gj]quinoline. Lysicamine is also a natural product found in Annona glabra.

Uses

Used in Pharmaceutical Industry:
Lysicamine is used as a cytotoxic agent for its ability to target and eliminate various human cancer cells. Its potent anticancer properties make it a valuable compound in the development of new cancer treatments.
Used in Chemical Enrichment:
Lysicamine can be enriched using response surface methodology and adsorption on macroporous resin. This application is significant in the chemical industry for improving the yield and purity of the compound, which can be further utilized in pharmaceutical and other research applications.

References

Katsui et al., Tetrahedron Lett., 6257 (1966)

InChI:InChI=1/C18H13NO3/c1-21-13-9-10-7-8-19-16-14(10)15(18(13)22-2)11-5-3-4-6-12(11)17(16)20/h3-9H,1-2H3

Upstream product

• 193551-54-1 (2-Bromo-phenyl)-(6,7-dimethoxy-isoquinolin-1-yl)-methanone 
• 260552-69-0 (±)-(2-bromophenyl)(6,7-dimethoxyisoquinolin-1-yl)methanol 
• 260552-68-9 (2-bromo-phenyl)-(6,7-dimethoxy-3,4-dihydro-[1]isoquinolyl)-ketone 

Relevant articles and documents

Aryl radical cyclizations of 1-(2′-bromobenzyl)isoquinolines with AIBN-Bu3SnH: Formation of aporphines and indolo[2,1-a]isoquinolines

(matrix presented) Radical cyclization of alkoxy-substituted 1-(2′-bromobenzyl)-3,4-dihydroisoquinolines 1 with AIBN-Bu3SnH gave 6a,7-dehydroaporphines 2 preferentially. A steric repulsion between the respective alkoxy groups at the 7- and 3′-positions gave 5,6-dihydroindolo[2,1-a]isoquinolines 3 in a disfavored 5-endo cyclization mode. Radical cyclizations of the related substrates, such as 1-(2′-bromobenzoyl)isoquinolines or 1-(2′-bromo-α-hydroxybenzyl)isoquinolines, were also found to give the corresponding oxoaporphines or oxyaporphines.