83-89-6

Basic information

• Product Name: QUINACRINE DIHYDROCHLORIDE DIHYDRATE
• Synonyms: 2-methoxy-6-chloro-9-diethylaminopentylaminoacridine;3-chloro-7-methoxy-9-(1-methyl-4-diethylaminobutylamino)acridine;6-chloro-9-((4-(diethylamino)-1-methylbutyl)amino)-2-methoxy-acridin;6-chloro-9-((4-(diethylamino)-1-methylbutyl)amino)-2-methoxyacridine;6-chloro-9-((4-(dimethylamino)-1-methylbutyl)amino)-2-methoxyacridine;acrichine;acrinamine;acriquine
• CAS NO: 83-89-6
• Molecular Formula: C₂₃H₃₀ClN₃O
• Molecular Weight: 508.91
• EINECS: 201-508-7
• Product Categories: ATABRINE
• Mol File: 83-89-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 247-250 °C
• Boiling Point: 557.1 °C at 760 mmHg
• Flash Point: 290.7 °C
• Appearance: /
• Density: 1.0989 (rough estimate)
• Refractive Index: 1.5790 (estimate)
• CAS DataBase Reference: QUINACRINE DIHYDROCHLORIDE DIHYDRATE(CAS DataBase Reference)
• NIST Chemistry Reference: QUINACRINE DIHYDROCHLORIDE DIHYDRATE(83-89-6)
• EPA Substance Registry System: QUINACRINE DIHYDROCHLORIDE DIHYDRATE(83-89-6)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 37/39-26
• Hazardous Substances Data: 83-89-6(Hazardous Substances Data)

Usage

Description

QUINACRINE DIHYDROCHLORIDE DIHYDRATE is a member of the acridine class, which is acridine substituted by a chloro group at position 6, a methoxy group at position 2, and a [5-(diethylamino)pentan-2-yl]nitrilo group at position 9. It is an organic compound with a chemical formula of C19H22Cl2N2O and is known for its yellow coloration and antimalarial properties.

Uses

Used in Anthelmintic Applications:
QUINACRINE DIHYDROCHLORIDE DIHYDRATE is used as an anthelmintic agent for treating various parasitic worm infections. It is effective in eliminating intestinal worms and reducing the associated symptoms and complications.
Used in Antimalarial Applications:
QUINACRINE DIHYDROCHLORIDE DIHYDRATE is used as an antimalarial agent, acting similarly to chloroquine. It was extensively used from the mid-1920s to the end of World War II due to its reasonable effectiveness against malaria-causing parasites.
Used as an Intercalating Agent:
QUINACRINE DIHYDROCHLORIDE DIHYDRATE is used as an intercalating agent in various applications, such as in the study of nucleic acids and their interactions with other molecules. Its ability to bind between the base pairs of DNA or RNA allows it to be used in research and diagnostic applications.
However, due to its side effects, such as causing the skin to turn yellow and yellow vision at high doses, QUINACRINE DIHYDROCHLORIDE DIHYDRATE is no longer in use as an antimalarial drug.

Safety Profile

Poison by intravenous and subcutaneous routes. Moderately toxic by ingestion. Mutation data reported. Experimental reproductive effects. Has been implicated in aplas tic anemia. When heated to decomposition, it emits very toxic fumes of Cland NOx.

InChI:InChI=1/C23H30ClN3O/c1-5-27(6-2)13-7-8-16(3)25-23-19-11-9-17(24)14-22(19)26-21-12-10-18(28-4)15-20(21)23/h9-12,14-16H,5-8,13H2,1-4H3,(H,25,26)

Upstream product

• 7478-26-4 6-chloro-2-methoxy-9-phenoxyacridine 
• 140-80-7 5-diethylamino-2-pentylamine 
• 83-89-6 quinacrine 
• 86-38-4 6,9-dichloro-2-methoxyacridine 
• 124-30-1 1-aminooctadecane 
• 108-95-2 phenol 
• 210584-71-7 6-chloro-2,9-dimethoxyacridine 
• 3548-09-2 6-chloro-2-methoxyacridin-9-amine 
• 2411-88-3 6-chloro-9-mercapto-2-methoxy-acridine 
• 57623-77-5 2-p-anisidino-4-chloro-benzoyl chloride 
• 4822-23-5 (6-chloro-2-methoxy-acridin-9-yl)-methyl-amine 
• 4822-25-7 N-(6-chloro-2-methoxy-acridin-9-yl)-acetamide 

Downstream Products

• 83-89-6 (+)-N⁴,N⁴-diethyl-N¹-(6-chloro-2-methoxy-acridin-9-yl)-1-methyl-butanediyldiamine 
• 83-89-6 (-)-N⁴,N⁴-diethyl-N¹-(6-chloro-2-methoxy-acridin-9-yl)-1-methyl-butanediyldiamine 

Relevant articles and documents

Lewis acid-catalyzed generation of C-C and C-N bonds on π-deficient heterocyclic substrates

Focused microwave irradiation of a series of halogenated nitrogen heterocycles and different kinds of nucleophiles in the presence of a catalytic amount of indium trichloride leads to the efficient and completely regioselective generation of aromatic C-C and C-N bonds. The method is simple, rapid, general and inexpensive, and can be performed without the use of dried solvents. Most of the synthetized compounds are new and in many cases the work-up required only filtration. Furthermore, this is the first example of the use of a Lewis acid as a catalyst for heteroarylation, vinylation and amination reactions on π-deficient heterocyclic substrates.

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