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Amsacrine

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Identification
Molecular formula
C21H19FN4O
CAS number
51264-14-3
IUPAC name
9-amino-N-[2-(dimethylamino)ethyl]-5-fluoro-acridine-4-carboxamide
State
State

At room temperature, amsacrine is a crystalline solid. It is used primarily in its solid state for pharmaceutical and laboratory applications.

Melting point (Celsius)
264.00
Melting point (Kelvin)
537.00
Boiling point (Celsius)
500.00
Boiling point (Kelvin)
773.00
General information
Molecular weight
393.45g/mol
Molar mass
393.4540g/mol
Density
1.3708g/cm3
Appearence

Amsacrine is typically an orange to red-orange crystalline solid. It is often provided as a fine powder for laboratory use and is sensitive to light, which can cause it to degrade.

Comment on solubility

Solubility of 9-amino-N-[2-(dimethylamino)ethyl]-5-fluoro-acridine-4-carboxamide

The solubility of the compound 9-amino-N-[2-(dimethylamino)ethyl]-5-fluoro-acridine-4-carboxamide (C21H19FN4O) can be quite complex due to its unique structure. Being an acridine derivative, it exhibits a combination of polar and non-polar characteristics which significantly influence its solubility behavior.

Factors Affecting Solubility:

  • Functional Groups: The presence of amino (-NH2) and carboxamide (-CONH2) groups typically increases solubility in polar solvents such as water.
  • Fluorine Substitution: The addition of fluorine can enhance lipophilicity, potentially decreasing solubility in aqueous environments.
  • Dimethylamino Group: This moiety may also contribute to increased solubility in polar organic solvents due to its basic nature.

In general, a common observation is that such compounds are more soluble in:

  • Dimethyl sulfoxide (DMSO)
  • Dimethylformamide (DMF)
  • Alcohols due to hydrogen bonding interactions.

However, the exact solubility may vary based on temperature, concentration, and the presence of other solvents in the mixture. It is essential to conduct empirical solubility tests to accurately determine the solubility of this compound in various solvents for practical applications.

Interesting facts

Interesting Facts about 9-amino-N-[2-(dimethylamino)ethyl]-5-fluoro-acridine-4-carboxamide

9-amino-N-[2-(dimethylamino)ethyl]-5-fluoro-acridine-4-carboxamide, commonly referred to in the scientific community as an acridine derivative, is a compound of significant interest due to its potential applications in the field of medicinal chemistry and drug development. Below are some noteworthy aspects of this fascinating compound:

  • Fluorine's Role: The presence of fluorine within the acridine structure enhances the compound's pharmacokinetic properties, including its solubility and bioavailability.
  • Mechanism of Action: This compound may interact with DNA, which is a common mechanism among many anticancer agents, leading to its potential use in therapeutic applications.
  • Dimethylamino Group: The dimethylamino moiety plays a crucial role in increasing the basicity of the compound, which can enhance interactions with biological targets.
  • Research Interest: Studies have indicated that acridine derivatives exhibit interesting biological activities, including antitumor, antibacterial, and anti-inflammatory effects, making this compound a valuable candidate for further research.
  • Structure-Activity Relationship: The unique combination of amino, fluoro, and acridine functionalities can lead to varied biological activities, emphasizing the importance of understanding structure-activity relationships in drug design.

As we delve deeper into the capabilities of 9-amino-N-[2-(dimethylamino)ethyl]-5-fluoro-acridine-4-carboxamide, it becomes clear that the compound stands as a promising scaffold for future medicinal applications. Its complexities exemplify the intricate connections between chemical structure and biological function, a core theme in the field of chemistry.

Synonyms
5-fluoro-9-amino-(n-(2-dimethylamino)ethyl)acridine-4-carboxamide
DA7
CHEMBL350028
Q27459130
9-amino-N-[2-(dimethylamino)ethyl]-5-fluoroacridine-4-carboxamide