3915-61-5

Basic information

• Product Name: 1-METHYL-2-P-DIMETHYLAMINO-STYRYL-QUINOLINIUM-IODIDE
• Synonyms: 1-METHYL-2-P-DIMETHYLAMINO-STYRYL-QUINOLINIUM-IODIDE;2-(4-DIMETHYLAMINOSTYRYL)-1-METHYLQUINOLINIUM IODIDE;2-(4-DIMETHYLAMINOSTYRYL)-1-METHYL-
• CAS NO: 3915-61-5
• Molecular Formula: C₂₀H₂₁N₂*I
• Molecular Weight: 416.3
• Mol File: 3915-61-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 261 °C (dec.)(lit.)
• Boiling Point: 458.3°C at 760 mmHg
• Flash Point: 208.7°C
• Appearance: /
• Density: 1.131g/cm³
• Vapor Pressure: 1.39E-08mmHg at 25°C
• Refractive Index: 1.687
• Solubility: DMSO: soluble
• CAS DataBase Reference: 1-METHYL-2-P-DIMETHYLAMINO-STYRYL-QUINOLINIUM-IODIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYL-2-P-DIMETHYLAMINO-STYRYL-QUINOLINIUM-IODIDE(3915-61-5)
• EPA Substance Registry System: 1-METHYL-2-P-DIMETHYLAMINO-STYRYL-QUINOLINIUM-IODIDE(3915-61-5)

Safety Data

• Hazard Codes: T
• Statements: 61-36/37/38
• Safety Statements: 53-26-36/37/39-45
• WGK Germany: 3
• F: 8-10
• Hazardous Substances Data: 3915-61-5(Hazardous Substances Data)

Usage

General Description

1-METHYL-2-P-DIMETHYLAMINO-STYRYL-QUINOLINIUM-IODIDE is a fluorescent molecule commonly used as a staining agent in biological research and diagnostics. It belongs to the styrylquinolines family of compounds and is known for its high affinity to cell membranes and its ability to bind to nucleic acids. This makes it useful for visualizing cell structures and studying cell function. The molecule emits a strong orange-red fluorescence when excited by light, making it a valuable tool for fluorescence microscopy and flow cytometry applications. Additionally, its high photostability and low cytotoxicity make it a preferred choice for long-term live-cell imaging studies.

InChI:InChI=1/C20H22N2/c1-21(2)18-12-8-16(9-13-18)10-14-19-15-11-17-6-4-5-7-20(17)22(19)3/h4-15,19H,1-3H3/b14-10+

Upstream product

• 64-17-5 ethanol 
• 19197-31-0 3-nitro-4'-(N,N-dimethylamino)benzylideneaniline 
• 876-87-9 N-methylquinaldinium iodide 
• 62-53-3 aniline 
• 17087-90-0 N-(4-dimethylaminobenzylidene)-p-toluidine 
• 15485-29-7 4-dimethylamino-benzaldehyde-(4-bromo-phenylimine) 
• 1749-04-8 N-(4-(N,N-dimethylamino)benzal)-p-anisidine 
• 889-37-2 N,N-dimethyl-4-((phenylimino)methyl)aniline 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 91-63-4 2-methylquinoline 
• 48189-64-6 2-(p-dimethylaminostyryl)quinoline 
• 74-88-4 methyl iodide 

Downstream Products

• 1246473-92-6 (E)-2-(4-(dimethylamino)styryl)-1-methylquinolinium 4-methoxybenzenesulfonate 
• 1246473-94-8 (E)-2-(4-(dimethylamino)styryl)-1-methylquinolinium 4-chlorobenzenesulfonate 
• 1246473-93-7 (E)-2-(4-(dimethylamino)styryl)-1-methylquinolinium 4-bromobenzenesulfonate 
• 1246473-91-5 (E)-2-(4-(dimethylamino)styryl)-1-methylquinolinium 4-methylbenzenesulfonate 
• 1246473-95-9 (E)-2-(4-(dimethylamino)styryl)-1-methylquinolinium 4-aminobenzenesulfonate 
• 24147-41-9 2-(4-dimethylamino-styryl)-3-methyl-benzooxazolium; toluene-4-sulfonate 

Relevant articles and documents

Design and Synthesis of Novel c-di-GMP G-Quadruplex Inducers as Bacterial Biofilm Inhibitors

The formation of biofilms by clinical pathogens typically leads to chronic and recurring antibiotic-resistant infections. High cellular levels of cyclic diguanylate (c-di-GMP), a ubiquitous secondary messenger of bacteria, have been proven to be associate

Design, synthesis and evaluation of 2-arylethenyl-N-methylquinolinium derivatives as effective multifunctional agents for Alzheimer's disease treatment

A series of 2-arylethenyl-N-methylquinolinium derivatives were designed and synthesized based on our previous research of 2-arylethenylquinoline analogues as multifunctional agents for the treatment of Alzheimer's disease (AD) (Eur. J. Med. Chem. 2015, 89, 349–361). The results of in vitro biological activity evaluation, including β-amyloid (Aβ) aggregation inhibition, cholinesterase inhibition, and antioxidant activity, showed that introduction of N-methyl in quinoline ring significantly improved the anti-AD potential of compounds. The optimal compound, compound a12, dramatically attenuated the cell death of glutamate-induced HT22 cells by preventing the generation of ROS and increasing the level of GSH. Most importantly, intragastric administration of a12?HAc was well tolerated at doses up to 2000 mg/kg and could traverse blood-brain barrier.

Design, synthesis and in vitro antitumour activity of new heteroaryl ethylenes

Almond and VolSurf + modelling procedures allowed the structural design of new di- and mono-heteroaryl-ethylenes. The structural modifications suggested by the molecular modelling were verified by the synthesis of the designed molecules and by the evaluation of their in vitro activities against two lung tumour cell lines, A549 and H226. 2-{(E)-2-[5′-(Dibutylamino)-2,2′- bithien-5-yl]vinyl}-1-methylquinolinium iodide exhibited in vitro antiproliferative activity two orders of magnitude higher than that of the most active compound previously synthesized in our laboratory.