58175-87-4

Basic information

• Product Name: (R)-Chloroquine
• Synonyms: (R)-Chloroquine;7-Chloro-4-[[(R)-4-(diethylamino)-1-methylbutyl]amino]quinoline;1,4-Pentanediamine, N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-, (4R)-;1,4-Pentanediamine, N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-, (R)-
• CAS NO: 58175-87-4
• Molecular Formula: C₁₈H₂₆ClN₃
• Molecular Weight: 319.87
• Mol File: 58175-87-4.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 460.6°C at 760 mmHg
• Flash Point: 232.3°C
• Appearance: /
• Density: 1.111g/cm³
• Vapor Pressure: 1.15E-08mmHg at 25°C
• Refractive Index: 1.592
• CAS DataBase Reference: (R)-Chloroquine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-Chloroquine(58175-87-4)
• EPA Substance Registry System: (R)-Chloroquine(58175-87-4)

Safety Data

• Hazardous Substances Data: 58175-87-4(Hazardous Substances Data)

Usage

Description

(R)-Chloroquine is an enantiomer of the drug chloroquine, a synthetic derivative of quinine, which is widely used as an antimalarial and autoimmune disease medication. It is known for its potent antiviral and anti-inflammatory properties, making it a potential treatment for various conditions.

Uses

Used in Antiviral Applications:
(R)-Chloroquine is used as an antiviral agent for inhibiting the replication of various viruses, including the coronavirus. Its activity against these viruses has garnered interest in its potential use as a treatment option.
Used in Autoimmune Disease Treatment:
(R)-Chloroquine is used as a medication for autoimmune diseases due to its immunomodulatory effects. It can suppress the production of inflammatory cytokines, which may help in managing the symptoms and progression of autoimmune conditions.
Used in Inflammatory Condition Management:
(R)-Chloroquine is used as an anti-inflammatory agent to manage inflammatory conditions. Its ability to suppress the production of inflammatory cytokines makes it a potential treatment option for such conditions.
However, it is important to note that the use of (R)-Chloroquine is limited due to potential toxicity and side effects. Ongoing research is being conducted to further evaluate its therapeutic potential and safety profile.

InChI:InChI=1/C18H26ClN3/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21)/t14-/m1/s1

Upstream product

• 54-05-7 Chloroquine 
• 105-14-6 5-diethylamino-2-pentanone 
• 86-98-6 4,7-dichloroquinoline 
• 67459-52-3 (S)-N¹,N¹-diethylpentane-1,4-diamine 
• 50-63-5 chloroquine phosphate 
• 140-80-7 5-diethylamino-2-pentylamine 
• 67459-50-1 (R)-(-)-4-amino-1-(diethylamino)pentane 
• 1198-40-9 4-amino-7-chloroquinoline 
• 77529-81-8 N,N-diethyl-(S)-glutamine hydrochloride 
• 77529-85-2 (S)-2-amino-5-(diethylamino)pentan-1-ol 
• 108-95-2 phenol 

Downstream Products

• 69698-56-2 (R)-chloroquine phosphate 
• 69698-56-2 (R)-chloroquine phosphate 

Relevant articles and documents

Enantioselective analyses of chloroquine and hydroxychloroquine in rat liver microsomes through chiral liquid chromatography–tandem mass spectrometry

An efficient, sensitive and selective liquid chromatography–tandem mass spectrometry (LC–MS/MS) chiral analysis method was established for determination of chloroquine and hydroxychloroquine enantiomers in rat liver microsomes. Effects of polysaccharide c

Preparation method and application of chiral chloroquine and phosphate thereof

The invention discloses a preparation method and application of chiral chloroquine and phosphate thereof. The method comprises the following steps: in a resolving solvent, salifying and crystallizing chloroquine racemate and a resolving agent to separate out crystals; performing primary recrystallizing, dissociating the crystals in an alkaline solution; filtering and separating out the resolving agent; performing extracting with an organic solvent, and drying and concentrating organic phases to respectively obtain corresponding (R)/(S)-chloroquine; and further salifying the (R)/(S)-chloroquine with phosphoric acid in the solvent to respectively obtain corresponding (R)/(S)-chloroquine phosphate. By adopting the method provided by the invention, the optical purity ee value of a finished product can be greater than 80% after primary crystallization, and the product with higher purity can be obtained by primary recrystallization. The crystals are good in crystal form and easy to filter and separate; the method is simple and convenient in resolution operation, free of tedious purification processes such as column separation, high in product optical purity, and relatively high in yield; and the resolving agent is reusable, so that production cost is low, and the method has a good industrial application prospect.

Preparation method of chiral aminochloroquinoline

The invention discloses a preparation method of chiral aminochloroquinoline, which comprises the following steps: splitting a chiral side chain, preparing enantiomer salt, splitting the side chain andchiral acid crystals to obtain chiral acid salt, neutralizing the chiral acid salt to obtain free basic groups, and reacting the free basic groups with 4, 7-dichloroquinoline to obtain chiral aminochloroquinoline. The yield of the chiral aminochloroquinoline obtained by the method is high, and the purity reaches 99.7%.