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Nitracrine

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Identification
Molecular formula
C23H22N4O3
CAS number
Neto known numer
IUPAC name
10-[3-(dimethylamino)propyl]-1-nitro-acridin-9-one
State
State

The compound is a solid at room temperature. It is generally stable under normal handling conditions but should be kept in airtight containers to prevent moisture absorption as it can slightly hygroscopic.

Melting point (Celsius)
244.00
Melting point (Kelvin)
517.00
Boiling point (Celsius)
550.00
Boiling point (Kelvin)
823.00
General information
Molecular weight
396.45g/mol
Molar mass
396.4530g/mol
Density
1.5400g/cm3
Appearence

Nitracrine appears as a yellow to orange crystalline powder. Its vibrant hue is characteristic of many acridine dyes, and the compound is often used in research settings for its distinct coloration. The powder is usually quite fine and needs to be handled with care to prevent dispersion in the air.

Comment on solubility

Solubility of 10-[3-(dimethylamino)propyl]-1-nitro-acridin-9-one

The solubility of 10-[3-(dimethylamino)propyl]-1-nitro-acridin-9-one in various solvents is a critical consideration for its applications in pharmaceuticals and organic chemistry. This compound exhibits unique solubility characteristics owing to its complex structure, which includes both hydrophobic and hydrophilic regions.

Key Solubility Features:

  • Solvent Type: It is generally more soluble in organic solvents such as ethanol and DMSO (dimethyl sulfoxide) compared to water. The dimethylamino group contributes to better solvation in polar organic solvents.
  • Hydrogen Bonding: The presence of the nitro group may enable some hydrogen bonding interactions, which can enhance solubility in polar solvents, albeit to a limited extent.
  • pH Dependence: The solubility may vary with pH changes, particularly due to the basic amine group that could become protonated, affecting solubility in aqueous solutions.

In practice, when working with this compound, it is advisable to consider the following:

  1. Conduct solubility tests in different solvents to determine the most effective medium for your specific application.
  2. Be aware of potential precipitation when shifting from organic to aqueous environments during experiments.
  3. Utilize solvent mixtures if necessary to enhance solubility and achieve optimal results.

As noted, a comprehensive understanding of solubility behavior is essential for effective utilization and handling of 10-[3-(dimethylamino)propyl]-1-nitro-acridin-9-one in research and application settings. Experimentation and consideration of these factors can significantly improve outcomes.

Interesting facts

Interesting Facts About 10-[3-(Dimethylamino)propyl]-1-nitro-acridin-9-one

This unique compound, known for its intriguing properties, has garnered attention in various scientific fields, particularly in medicinal chemistry and photophysics. Here are some captivating aspects of this compound:

  • Versatile Chemotherapeutic Applications: The acridine skeleton of this compound is well-studied for its biological activities, including its role as an antitumor agent. Acridines interact with DNA, which can lead to the inhibition of replicative processes that are pivotal in cancer growth.
  • Fluorescent Properties: The presence of the nitro group enhances the fluorescence characteristics of this compound, making it useful in imaging techniques. This property allows scientists to track molecular interactions in biological systems.
  • Structure-Activity Relationship: The incorporation of the dimethylamino group is of particular interest. It can influence the compound's overall pharmacological profile and biological activity by enhancing solubility and altering interactions with target molecules.
  • Potential for Drug Development: The unique modifications made to the acridine backbone have made this compound a template for the design of new derivatives with improved efficacy and reduced toxicity for potential therapeutic use.
  • Research Opportunities: As a relatively complex molecule, it presents numerous challenges and opportunities for students and researchers alike, from synthetic routes to studying its interaction with biological systems.

In summary, 10-[3-(dimethylamino)propyl]-1-nitro-acridin-9-one stands out as a compound with significant promise in both research and application, offering valuable insights into the realms of chemistry and pharmacology. Its structural uniqueness, coupled with its versatile biological activity, makes it a subject of continued exploration.

Synonyms
1-Nitro-10-(3-dimethylaminopropyl)acridone hydrochloride
22108-26-5
10-(3-(Dimethylamino)propyl)-1-nitro-9(10H)-acridinone, monohydrochloride
RefChem:76552
10-[3-(dimethylamino)propyl]-1-nitroacridin-9-one
DTXSID60176619
1-Nitro-10-(3-dimethylaminopropyl)acridone
9(10H)-Acridinone, 10-(3-(dimethylamino)propyl)-1-nitro-