Product Number: D023016A
English Name: Dequalinium Impurity 16(Hydrochloride)
English Alias: 2-methyl-N-phenylquinolin-4-amine hydrochloride
CAS Number: 879662-14-3
Molecular Formula: C₁₆H₁₄N₂.HCl
Molecular Weight: 234.30 36.46
As an impurity of Dequalinium (in hydrochloride form), this compound has the following advantages:
Well-defined and distinct structure: Contains quinoline ring, methyl group, N-phenylamino group, and hydrochloride moiety, lacking the bis-quinoline and long-chain linkage of dequalinium. Synergistic effects of quinoline conjugation, amine, and chloride enable unique polarity and retention, allowing accurate identification via HPLC and LC-MS as a specific impurity marker;
High stability and traceability: Quinoline-amine conjugation and hydrochloride ionic bonding ensure stability under acidic conditions. As an incomplete condensation by-product in dequalinium synthesis, it directly reflects amination efficiency, improving process tracing accuracy;
High detection sensitivity: Strong UV absorption (260-280nm) from quinoline, combined with characteristic mass response of free base (m/z 235 [M+H]⁺), enables trace analysis via LC-MS (ppb level), compatible with bis-quinoline disinfectant impurity systems.
Pharmaceutical quality control: Used as a reference standard to quantify Dequalinium Impurity 16(Hydrochloride) in APIs and formulations, ensuring residual mono-quinoline impurities meet quality standards;
Synthesis optimization: Optimizing 2-methylquinoline-aniline amination (catalyst, temperature) by monitoring impurity levels to enhance bis-quinoline condensation efficiency;
Impurity profile enrichment: Contributing to dequalinium’s impurity profile for comprehensive purity assessment and regulatory submissions.
Dequalinium, a bis-quinoline cationic disinfectant for oral infections, is synthesized via condensation of two 2-methylquinoline molecules with aromatic amines. Incomplete condensation may leave mono-quinoline derivatives like 2-methyl-N-phenylquinolin-4-amine, which forms Dequalinium Impurity 16(Hydrochloride) upon hydrochlorination. Its weaker antibacterial activity and potential stability impacts make control critical for dequalinium quality assurance.
Current research focuses on:
Analytical method validation: Developing UPLC-MS/MS assays with hydrochloride-optimized parameters for simultaneous quantification of impurity and dequalinium, achieving 0.1 ppb detection limits;
Condensation kinetics: Studying impurity formation under varying reactant ratios to clarify bis-quinoline synthesis mechanisms;
Process refinement: Controlling impurity levels below 0.1% via optimized condensation conditions to enhance API purity;
Formulation compatibility: Evaluating interactions between the impurity and excipients to ensure stability of dequalinium formulations during shelf life
China
