9-Aminoacridine
[CAS# 90-45-9]

Identification

• Classification: API >> Synthetic anti-infective drugs >> Disinfectant antiseptic
• Name: 9-Aminoacridine
• Synonyms: 9AA; Aminacrin; Aminacrine; Izoacridina; Monacrin; NSC 13000; NSC 28747
• Molecular Formula: C₁₃H₁₀N₂
• Molecular Weight: 194.23
• CAS Registry Number: 90-45-9
• EC Number: 201-995-6
• SMILES: C1=CC=C2C(=C1)C(=C3C=CC=CC3=N2)N

Properties

• Solubility: 10 mM (DMSO)
• Density: 1.3±0.1 g/cm³, Calc.^*, 1.268 g/mL (Expl.)
• Melting point: 238-240 ºC (Expl.)
• Index of Refraction: 1.780, Calc.^*
• Boiling Point: 413.5±20.0 ºC (760 mmHg), Calc.^*
• Flash Point: 233.2±9.0 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

9-Aminoacridine is a chemical compound with the molecular formula C9H8N2. It belongs to the family of acridines, which are a group of aromatic compounds known for their fluorescent properties and potential biological activity. This compound consists of an acridine skeleton with an amino group attached at the 9-position, giving it unique chemical and physical characteristics that make it valuable in a variety of scientific fields.

The discovery of 9-aminoacridine can be traced back to the early 20th century when researchers were exploring the structure-activity relationships of acridine derivatives. Acridine itself was first synthesized in the 19th century and was known for its use in dyes and its characteristic fluorescence. Scientists soon began to investigate modifications to the basic acridine structure to enhance its properties or create new functionalities, which led to the synthesis of various derivatives, including 9-aminoacridine.

The amino group on the 9-position of the acridine ring significantly alters the compound's chemical reactivity and its ability to interact with biological systems. This modification has made 9-aminoacridine an important molecule in both medicinal chemistry and materials science. One of its most notable features is its ability to intercalate with DNA, a property that has made it a useful tool in biological research and as a potential therapeutic agent.

In terms of its biological applications, 9-aminoacridine has been studied for its role as an anti-cancer agent. Its ability to intercalate into the DNA helix disrupts the normal functioning of DNA, which can lead to the inhibition of DNA replication and transcription. This mechanism of action makes 9-aminoacridine a potential candidate for the development of anti-cancer drugs. It has been investigated in preclinical studies for its cytotoxic effects on cancer cells, although further research is needed to assess its efficacy and safety in clinical applications.

9-Aminoacridine is also known for its use as a fluorescent probe in molecular biology. Due to its ability to bind to nucleic acids, it can be used to visualize and study DNA and RNA in vitro. It has been employed in various fluorescence-based assays, including those used to detect DNA damage, as well as in assays to study the interactions between small molecules and nucleic acids. Its fluorescence properties are valuable for monitoring the binding interactions between 9-aminoacridine and DNA, providing insights into the mechanisms of DNA-drug interactions.

In addition to its biological applications, 9-aminoacridine has found use in the development of light-emitting devices and organic semiconductors. Its fluorescent properties make it an attractive candidate for incorporation into materials that require optical activity, such as light-emitting diodes (LEDs) and organic solar cells. The development of acridine-based compounds for electronic applications is an area of active research, and 9-aminoacridine's properties make it a promising candidate for further exploration.

In conclusion, 9-aminoacridine is a versatile compound with significant potential in both medicinal and materials science. Its ability to intercalate with DNA and its fluorescent properties make it an important tool in molecular biology and a candidate for the development of anti-cancer therapies. Additionally, its utility in electronic applications highlights the broad range of possibilities for this unique chemical substance.