Description
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Identity & Molecular Data
- Chemical name: (-)-Quinine hydrochloride dihydrate
- CAS #: 6119‑47‑7 
- EC number: 205‑001‑1 
- Molecular formula: C₂₀H₂₅ClN₂O₂·2 H₂O
- Molar mass: ~396.9 g/mol 
- Optical rotation: –230 ± 5° ([α]²⁰/D) 
Physical Properties
- Appearance: White to off-white powder 
- Melting point: 115–116 °C (decomposes) 
- Solubility: ~62.5 g/L in water; also cited as 0.25 mg in 5 mL H₂O in pharma tests 
- pH: ~6.0 when 1% solution at 20 °C  
- Bulk density: ~310 kg/m³ 
Applications & Uses
- Antimalarial medication: Especially for Plasmodium falciparum resistant to chloroquine, used orally or IV 
- Fluorometric reagent: Commonly used in fluorescence assays (excitation/emission: ~322/450 nm in water) 
- Actinometry: Employed for measuring light in photochemical research 
Mode of Action & Pharmacology
- Antimalarial mechanism: Inhibits hemozoin formation in parasites, disrupting digestion of hemoglobin; may also inhibit nucleic-acid synthesis and glycolysis 
- Other effects: Potassium channel blockade in enteric neurons; acts as blood schizonticide 
Safety & Handling
- Hazard classification: Oral acute tox 4; respiratory/skin sensitizer 
- LD₅₀ (rat, oral): ~620 mg/kg 
- Hazard statements: Harmful if swallowed; may cause allergic skin reactions and asthma; handle with care 
- Precautions: Wear gloves, eye protection, dust mask (N95), work in ventilated area; avoid dust inhalation 
- Storage: Below +30 °C; dispose per organic reagent guidelines 
Regulatory Status & Warnings
- Medical use: Approved for malaria; no longer first-line due to alternatives; off-label use for leg cramps discouraged by FDA & FDA bans OTC usage for cramps 
- Side effects: Cinchonism (headache, tinnitus, visual changes); severe reactions include arrhythmia, thrombocytopenia, hemolytic anemia, renal failure 
- Contraindications: Avoid in G6PD deficiency, heart conduction disorders; interacts via CYP2D6 inhibition 
- Food & beverage uses: Flavoring agent in tonic water, limited to ≤100 mg/L in EU and ≤83 ppm in US 
Industry & Research Use
- Pharmacopeia grade: Compliant with USP/NF and Ph.Eur standards 
- Research grade: Pure, fluorescent-grade powder (≥98%), used in spectroscopy and fluorescence studies 
Trivia & Anecdotes
- Tonic water’s origin: Developed to mask quinine’s bitterness; gin and tonic originated from this practice 
- Fluorescence: Under UV light, quinine glows cyan—often used in fun demos 
Property | Value |
---|---|
CAS | 6119‑47‑7 |
Formula | C₂₀H₂₅ClN₂O₂·2 H₂O |
Mol. mass | ~396.9 g/mol |
Melting point | 115–116 °C (decomp.) |
Solubility | ~62.5 g/L (∞ water), pH ~6 |
Hazard | Acute oral tox; skin/lung sensitizer; LD₅₀ ≈ 620 mg/kg (rat) |
Uses | Antimalarial; fluorescent reagent; flavoring |
Regulatory notes | Restricted for leg cramps (US); limited beverage presence |
Pharmacology | Blood schizonticide; CYP2D6 inhibitor; may cause cinchonism |
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