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Amsacrine

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Identification
Molecular formula
C21H20Cl4N2O
CAS number
51264-14-3
IUPAC name
bis(2-chloroethyl)-[2-[(6-chloro-2-methoxy-acridin-9-yl)ammonio]ethyl]ammonium;dichloride
State
State

At room temperature, the compound exists as a solid.

Melting point (Celsius)
278.00
Melting point (Kelvin)
551.15
Boiling point (Celsius)
208.00
Boiling point (Kelvin)
481.15
General information
Molecular weight
457.84g/mol
Molar mass
457.8410g/mol
Density
1.3400g/cm3
Appearence

Bis(2-chloroethyl)-[2-[(6-chloro-2-methoxy-acridin-9-yl)ammonio]ethyl]ammonium dichloride typically presents as a yellow to orange crystalline powder.

Comment on solubility

Solubility of Bis(2-chloroethyl)-[2-[(6-chloro-2-methoxy-acridin-9-yl)ammonio]ethyl]ammonium; Dichloride

The solubility of the compound bis(2-chloroethyl)-[2-[(6-chloro-2-methoxy-acridin-9-yl)ammonio]ethyl]ammonium; dichloride (C21H20Cl4N2O) is influenced by several factors related to its molecular structure and the presence of chlorinated and ammonium groups.

Factors Affecting Solubility

  • Molecular Polarity: The presence of polar functional groups, such as the ammonium cation, increases the interaction with polar solvents, thereby enhancing solubility in w aqueous environments.
  • Chlorine Atoms: The multiple chlorine atoms in the structure contribute to its overall polarity while influencing intermolecular forces like dipole-dipole interactions.
  • Solvent Choice: This compound is likely to be soluble in organic solvents due to its large hydrocarbon framework, although solubility may vary significantly in aqueous solutions.

In summary, while the presence of ionic and polar components may suggest a degree of solubility in water, the overall behavior of bis(2-chloroethyl)-[2-[(6-chloro-2-methoxy-acridin-9-yl)ammonio]ethyl]ammonium; dichloride is subject to extensive testing to determine its exact solubility characteristics in various solvents. Understanding these aspects is crucial for practical applications in pharmaceuticals and chemical research.

Interesting facts

Interesting Facts about Bis(2-chloroethyl)-[2-[(6-chloro-2-methoxy-acridin-9-yl)ammonio]ethyl]ammonium; Dichloride

Bis(2-chloroethyl)-[2-[(6-chloro-2-methoxy-acridin-9-yl)ammonio]ethyl]ammonium; dichloride is a fascinating compound mainly known for its applications in the field of medicinal chemistry. Here are some key points that highlight its significance:

  • Pharmaceutical Relevance: This compound belongs to a class of alkylating agents which are often utilized in cancer treatment. Its ability to interfere with DNA replication makes it a valuable tool in chemotherapy.
  • Mechanism of Action: The alkylating mechanism involves the formation of covalent bonds with DNA, leading to cross-linking. This inhibits the cancer cell's ability to divide and grow, contributing to its therapeutic effects.
  • Specific Design: The incorporation of extra functional groups such as the 6-chloro-2-methoxy-acridin-9-yl moiety not only enhances its activity but may also improve selectivity towards cancer cells over healthy ones.
  • Research Insights: Research suggests that derivatives of this compound could have improved potency and reduced side effects compared to traditional treatments, leading to ongoing studies in optimizing its chemical structure.
  • Toxicity Concerns: As with many potent drugs, understanding the toxicity profile is crucial. Investigations into its side effects and interactions with other drugs are vital for maximizing its therapeutic potential.

The compound serves as a prime example of how the intricate design of chemical entities can lead to significant advances in the treatment of serious diseases. As researchers delve deeper into its properties, the hope is to refine such compounds for better efficacy and safety in clinical applications.

Synonyms
Quinacrine ethyl mustard
ICR-48b
NSC-34372
NSC 34372
9-(2-(Di(2-chloroethyl)amino)ethylamino)-6-chloro-2-methoxyacridine
Acridine, 9-(2-(bis(2-chloroethyl)amino)ethylamino)-6-chloro-2-methoxy-, dihydrochloride, hydrate
Acridine, 9-((2-(bis(2-chloroethyl)amino)ethyl)amino)-6-chloro-2-methoxy-, dihydrochloride