130-89-2

Basic information

• Product Name: QUININE HCL
• Synonyms: QUININE HCL;QUININE HYDROCHLORIDE;QUININE MONOHYDROCHLORIDE;6’-methoxy-,monohydrochloride,(8.alpha.,9R)-Cinchonan-9-ol;6’-methoxy-,monohydrochloride,(8-alpha,9r)-cinchonan-9-o;6’-methoxy-,monohydrochloride,(8alpha,9theta)-cinchonan-9-o;chinimetten;quininechloride
• CAS NO: 130-89-2
• Molecular Formula: C₂₀H₂₄N₂O₂*ClH
• Molecular Weight: 360.88
• EINECS: 205-001-1
• Mol File: 130-89-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 158-160 C
• Boiling Point: 495.9 °C at 760 mmHg
• Flash Point: 253.7 °C
• Appearance: /
• Density: 1.1206 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5400 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO (Slightly), Ethanol (1g/1ml), glycerol(1g/7ml), chloroform(1g/1ml)
• Water Solubility: 549.7mg/L(25 oC)
• CAS DataBase Reference: QUININE HCL(CAS DataBase Reference)
• NIST Chemistry Reference: QUININE HCL(130-89-2)
• EPA Substance Registry System: QUININE HCL(130-89-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• RIDADR: 1544
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 130-89-2(Hazardous Substances Data)

Usage

Chemical Properties

Quinine hydrochloride is a white, silky, glittering needles; odourless, effloresces when exposed to warm air. Soluble in water, very soluble in ethanol, freely soluble in chloroform, insoluble in ether. Its solutions are neutral or alkaline to litmus. It is an alkaloid derived from the bark of the cinchona tree. Quinine Hydrochloride is used as ingredient of beverages and injection medication.

Uses

Quinine Hydrochloride is used as an antimalarial drug, and is the active ingredient in extracts of the cinchona that have been used for that purpose since before 1633. Quinine is also a mild antipyretic and analgesic and has been used in common cold preparations for that purpose. It was used commonly and as a bitter and flavoring agent, and is still useful for the treatment of babesiosis. Quinine is also useful in some muscular disorders, especially nocturnal leg cramps and myotonia congenita, because of its direct effects on muscle membrane and sodium channels. The mechanisms of its antimalarial effects are not well understood.

Definition

Quinine Hydrochloride is the hydrochloride of a natural substance, quinine, obtained from the bark of various species of Cinchona including Cinchona succirubra, Pavon. (red cinchona); Cinchona officinalis, Linn; Cinchona calizaya, Wenddell; Cinchona ledgeriana, Moens. It is a nature-derived bitter flavoring agent for tonic water, among other beverages.

Biological Activity

Quinine hydrochloride is a displays antimalarial and muscle relaxant properties. Stereoisomer of quinidine; closely related to chloroquine.?

Safety Profile

Poison by ingestion, subcutaneous, intravenous, intramuscular, and intraperitoneal routes. Human systemic effects by intravenous route: convulsions or effect on seizure threshold, muscle contraction or spasticity, and nausea or vomiting. Mutation data reported. Used as a local anesthetic. When heated to decomposition it emits very toxic fumes of NO, and HCI. See also QUININE.

Synthesis

Manufacture of quinine by extraction from Cinchona bark and subsequent purification and synthesis to quinine hydrochloride.

InChI:InChI=1/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14+,19-,20+/m0/s1

Upstream product

• 76-60-8 bromocresol green 
• 121-54-0 benzethonium cloride 
• 56-54-2 quinine 
• 130-95-0 Quinine 
• 115-39-9 bromophenol blue 

Downstream Products

• 522-66-7 dihydroquinine 

Relevant articles and documents

Multiple-responsive ionic complex luminogen of quinine and camphorsulfonic acid with aggregation-induced emission

Bulky camphorsulfonic acid (CSA) was used to complex with quinine (Qu) to impose restricted intramolecular rotation (RIR) required for aggregation-induced emission (AIE) properties. After complexation with two equivalents of CSA, the non-emissive quinine (Qu) base can be protonated to produce an ionic complex Qu(CSA)2 with AIE properties. The ionic bonds in the complex Qu(CSA)2 are sensitive to various external stimuli, which allows its use as a luminescent sensor for pH values and different metal ions. Moreover, the ionic Qu(CSA)2 can be a denaturant and biological sensor for the blood protein of bovine serum albumin (BSA); through the use of Qu(CSA)2, the unfolding process of the BSA chains was evaluated. Theoretical and practical aspects of this ionic Qu(CSA)2 complex are discussed in this study.

Substitution reactions of benzethonium chloride with ion associates of bromocresol green - quinine and bromophenol blue - quinine in dichlormethane

An excess concentration of base quinine (Q) reacts with a sulphonphthalein diacidic dye XH2, (bromocresol green, BCGH2, or bromophenol blue, BPBH2) in dichlormethane solution to form an ion associate (X(2-)(QH21+)2) of stoichiometry 1:2 (dye:amine).Benzethonium chloride (CIB) reacts with the 1:2 ion associate to form an ion associate (QH1+,X2-,B1+) and quinine hydrochloride ClQH(1+).This substitution reaction is a chemical equilibrium with formation constants of 1.50+/-0.67, 1.64+/-0.54, 1.07+/-0.29, 1.04+/-0.20, and 0.84+/-0.26 for BCG and 1.86+/-0.59, 1.47+/-0.23, 1.40+/-0.65, 1.13+/-0.37, and 1.11+/-0.27 for BPB at 283.16, 288.16, 293.16, 298.16, and 303.16 K respectively.The thermodynamic parameters determined by van't Hoff's equation are ΔH0 = -21.766+/-7.482 kJmol-1, ΔS0 = -73+/-51 Jmol-1K-1, and ΔG0 = -1.134+/-0.972 kJmol-1 for BCG and ΔH0 = -18.678+/-7.482 kJmol-1, ΔS0 = -61+/-26 Jmol-1K-1, ΔG0 = -0.916+/-0.401 kJmol-1 for BPB (ΔG0 at 293.16K; and ΔH0 and ΔS0 determined in the range 283-303K). Key words: bromocresol green-quinine-benzetonium, ion associate mixture, bromophenol blue-quinine-benzethonium, equilibrium constants, thermodynamic parameters.