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Amsacrine

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Identification
Molecular formula
C21H19Cl2N3O
CAS number
51264-14-3
IUPAC name
N-(2-chloroethyl)-N'-(6-chloro-2-methoxy-acridin-9-yl)ethane-1,2-diamine
State
State

At room temperature, Amsacrine is typically found as a solid, in the form of a crystalline powder. It is used primarily in its solid form for pharmaceutical applications.

Melting point (Celsius)
263.00
Melting point (Kelvin)
536.15
Boiling point (Celsius)
452.00
Boiling point (Kelvin)
725.15
General information
Molecular weight
393.32g/mol
Molar mass
393.8710g/mol
Density
1.4231g/cm3
Appearence

Amsacrine is an orange to red crystalline powder. It tends to appear slightly granular and can be visually striking due to its intense color.

Comment on solubility

Solubility of N-(2-chloroethyl)-N'-(6-chloro-2-methoxy-acridin-9-yl)ethane-1,2-diamine

The solubility of N-(2-chloroethyl)-N'-(6-chloro-2-methoxy-acridin-9-yl)ethane-1,2-diamine can be influenced by a variety of factors due to its complex structure. Being a diamine derivative, its solubility characteristics can be characterized as follows:

  • Polarity: The presence of chloro groups and methoxy functionality can affect the overall polarity, potentially enhancing solubility in polar solvents such as water.
  • Solvent Interaction: It may display enhanced solubility in organic solvents like ethanol or dimethyl sulfoxide (DMSO) due to the hydrophobic aromatic system present in its structure.
  • Protonation: The amine groups might increase solubility in acidic conditions when they become protonated, allowing for better interaction with water.
  • Temperature Dependence: Like many organic compounds, solubility may increase with temperature, facilitating dissolution.

It is important to note that the solubility can vary widely based on specific environmental conditions. As a rule of thumb, compounds with a higher proportion of polar functional groups tend to exhibit improved solubility in polar media. In summary, while the solubility of this compound might be somewhat moderate in standard conditions, adjustments in factors such as solvent choice or pH can drastically alter its solubility profile.

Interesting facts

Interesting Facts About N-(2-chloroethyl)-N'-(6-chloro-2-methoxy-acridin-9-yl)ethane-1,2-diamine

N-(2-chloroethyl)-N'-(6-chloro-2-methoxy-acridin-9-yl)ethane-1,2-diamine is a fascinating compound that showcases the intersection of medicinal and organic chemistry. This compound belongs to a class of chemicals known for their potential therapeutic applications, particularly in the field of oncology.

Key Features and Applications

  • Cytotoxicity: This compound demonstrates properties that could lead to the inhibition of cancer cell growth, making it a candidate for further research in anti-cancer drug development.
  • Mechanism of Action: The presence of the acridine moiety is significant, as acridines are known to intercalate into DNA, potentially disrupting the replication process of malignant cells.
  • Potential Side Effects: Like many compounds that target rapidly dividing cells, understanding its side effect profile is crucial for safe therapeutic use.

Interestingly, this compound's structure is a blend of synthetic chemistry and pharmacology, illustrating how modifications in molecular structure can enhance bioactivity. The incorporation of a chloroethyl group aids in the compound's reactivity, whereas the methoxy group enhances its solubility, an essential characteristic for drug formulation.

Research Opportunities

Due to its intriguing properties, this compound invites a range of research opportunities:

  • Drug Development: Scientists can explore its efficacy in various cancers, aiming to substantiate its role as a therapeutic agent.
  • Structural Analogues: Modifying the compound could lead to analogues that may exhibit improved potency or reduced toxicity.
  • Mechanistic Studies: Understanding how this compound interacts with biological macromolecules can provide insights into its mechanism and the broader implications for drug design.

In summary, N-(2-chloroethyl)-N'-(6-chloro-2-methoxy-acridin-9-yl)ethane-1,2-diamine is not just a chemical entity but a potential beacon in the search for effective cancer treatments. Its unique structural characteristics and biological interactions open up a world of exploration for chemists and pharmacologists alike.

Synonyms
72667-34-6
1,2-Ethanediamine, N-(6-chloro-2-methoxy-9-acridinyl)-N'-(2-chloroethyl)-
BRN 0442018
N-(6-Chloro-2-methoxy-9-acridinyl)-N'-(2-chloroethyl)-1,2-ethanediamine
DTXSID80222980