N-Nitroso Desmethyl Citalopram
Product Number: N031095
English Name: N-Nitroso Desmethyl Citalopram
English Alias: N-(3-(5-cyano-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)propyl)-N-methylnitrous amide
CAS Number: None
Molecular Formula: C₁₉H₁₈FN₃O₂
Molecular Weight: 339.36
As a nitroso impurity of Desmethyl Citalopram, this compound has the following advantages:
Well-defined with distinct functional groups: Contains isobenzofuran ring, 5-cyano, 1-(4-fluorophenyl), and 3-(N-methylnitrous amide)propyl. Unlike desmethyl citalopram, its nitrosoamide (-N-NO) polarity, fluorine electronegativity, and polycyclic hydrophobicity create significant differences, enabling precise differentiation via HPLC/ion-pair chromatography as a specific marker;
High stability and traceability: Rigid isobenzofuran structure and stability of cyano/nitrosoamide ensure stability under dark, low-temperature conditions. As a derivative from amine nitrosation during storage/synthesis, it directly reflects amino stability and nitrite exposure, improving impurity tracing accuracy;
High detection sensitivity: Polycyclic conjugation shows strong UV absorption (230-270nm), combined with m/z 340 [M+H]⁺ enabling ppb-level analysis via LC-MS, compatible with SSRI nitroso impurity systems.
Pharmaceutical quality control: Used as an impurity reference standard to quantify N-Nitroso Desmethyl Citalopram in APIs, ensuring compliance with genotoxic impurity limits in pharmaceutical standards;
Stability studies: Monitoring impurity levels under varying conditions (pH, light) to assess degradation trends and support shelf-life assurance;
Synthesis assessment: Evaluating purity of demethylated intermediates in citalopram synthesis to reduce nitrosation risk at the source.
Desmethyl citalopram, a major citalopram metabolite, contains an N-methylamino group that may undergo nitrosation upon exposure to nitrous acid (e.g., from nitrate reduction), forming N-methylnitrous amide derivatives like N-Nitroso Desmethyl Citalopram. Due to potential genotoxicity, nitroso impurities are strictly regulated, and their residues may affect citalopram safety, making detection and control critical for quality assurance.
Current research focuses on:
Analytical method validation: Developing UPLC-MS/MS methods with C18 columns for separation, achieving 0.01 ppb detection limits;
Nitrosation mechanism: Studying impurity formation kinetics under varying nitrite concentration and pH to clarify N-methylamino-to-nitrosoamide conversion pathways;
Control strategies: Exploring nitrosation inhibitors (e.g., ascorbic acid) to keep impurity levels below safety limits (<0.001%);
Toxicity evaluation: Conducting in vitro genotoxicity tests (e.g., Ames test) to assess potential hazards and support limit setting.
We can also customize related analogues and modified peptides including HPLC, MS, 1H-NMR, MS, HPLC, IR, UV, COA, MSDS.
This product is intended for laboratory use only!
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