9-Aminoacridine

Base Information

• Chemical Name: 9-Aminoacridine
• CAS No.: 90-45-9
• Deprecated CAS: 148651-03-0
• Molecular Formula: C₁₃H₈N₂
• Molecular Weight: 192.22
• Hs Code.: 2933 99 80
• European Community (EC) Number: 201-995-6
• NSC Number: 757794,28747,13000
• UNII: 78OY3Z0P7Z
• DSSTox Substance ID: DTXSID2024456
• Nikkaji Number: J761.367I,J3.917I
• Wikipedia: 9-Aminoacridine
• Wikidata: Q513937
• NCI Thesaurus Code: C77023
• Pharos Ligand ID: 5LWVP3BZCFM1
• Metabolomics Workbench ID: 133983
• ChEMBL ID: CHEMBL43184
• Mol file: 90-45-9.mol

Synonyms:9 Aminoacridine;9-Aminoacridine;Acridinamine;Aminacrine;Aminacrine Hydrochloride;Aminoacridine;Aminoacridine Hydrochloride;Aminopt;Hydrochloride, Aminacrine;Hydrochloride, Aminoacridine;Mykocert

Chemical Property of 9-Aminoacridine

Chemical Property:

• Appearance/Colour: yellow crystals or powder
• Vapor Pressure: 4.76E-07mmHg at 25°C
• Melting Point: 241 C
• Refractive Index: 1.5014 (estimate)
• Boiling Point: 413.5°C at 760 mmHg
• PKA: 9.99(at 20℃)
• Flash Point: 233.2°C
• PSA: 38.91000
• Density: 1.268
• LogP: 3.55140
• Storage Temp.: Store below +30°C.
• Solubility.: ethanol: hazy
• Water Solubility.: 11.65mg/L(24 oC)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 194.084398327
• Heavy Atom Count: 15
• Complexity: 207

Purity/Quality:

99% ^*data from raw suppliers

9-Aminoacridine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=C3C=CC=CC3=N2)N
• General Description: 9-Aminoacridine (9AA) is an anticancer compound that can be conjugated to bi-nuclear amino acid platforms (MAAPs) for targeted drug delivery, where its cytotoxicity is "switched off" in the conjugated state and "switched on" upon release in cancer cells. This approach enhances specificity and reduces off-target effects, demonstrating its potential in modular drug delivery systems for cancer therapy.

Technology Process of 9-Aminoacridine

There total 34 articles about 9-Aminoacridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

acridin-9-amine hydrochloride (134-50-9) → aminacrine (110166-26-2,90-45-9)

Guidance literature:

With sodium hydroxide; In water; ethyl acetate; for 0.25h; Concentration; Reagent/catalyst; Solvent;

Reference yield: 96.0%

9-Chloroacridine (1207-69-8) + ethylamine (75-04-7,85404-22-4) → aminacrine (110166-26-2,90-45-9)

Guidance literature:

With ammonia; In dimethyl sulfoxide; at 120 ℃; for 3h; Solvent; Temperature;

Reference yield: 95.0%

1-acridin-9-yl 3-tert-butylurea → aminacrine (110166-26-2,90-45-9)

Guidance literature:

In 5,5-dimethyl-1,3-cyclohexadiene; for 1h; Reflux;

DOI:10.1016/j.tetlet.2016.06.103

upstream raw materials:

9-Chloroacridine

9-azidoacridine

diethyl-thiophosphinsaeure-S-n-butylester

acridin-9-hydroxamsaeure

Downstream raw materials:

N'-phenyl-N-(acridyl-9) thiocarbamide

N-Acridin-9-yl-2-benzhydrylsulfanyl-nicotinamide

Refernces

Switch off/switch on regulation of drug cytotoxicity by conjugation to a cell targeting peptide

10.1016/j.ejmech.2014.07.073

This research aimed to develop a "switch off/switch on" regulation of drug cytotoxicity for targeted cancer therapy by conjugating anticancer drugs to bi-nuclear amino acid platforms (MAAPs) through solid-phase organic synthesis (SPOS). The purpose was to enhance the therapeutic efficacy of multiple drugs linked to a single carrier molecule, potentially improving target cell specificity and reducing side effects. The researchers synthesized MAAPs loaded with various anticancer agents, including Azatoxin (AZA), Camptothecin (CAMP), Prednisone (PRED), Chlorambucil (CLB), and the 9-aminoacridine anticancer compound YG-42. They demonstrated that the cytotoxic activity of these drugs could be controlled by chemical modification and delivery, effectively "switching off" the activity when conjugated to the MAAP and "switching on" when delivered to target cancer cells via a cell-targeting peptide. The conclusions supported the versatility of this approach for constructing MAAPs with various drugs and linkages, showing high variability in bio-stability and drug release kinetics. This research paves the way for more sophisticated MAAPs bearing diverse chemotherapeutic "cocktails" for preclinical cancer therapy assessment.

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