N-Nitroso Desmethyl Doxycycline NEW

N-Nitroso Desmethyl Doxycycline

WhatsAPP: +86 17386083646
E-mail: anna@molcoo.com

Product Information

Product Information

• Product Number: D036003

• English Name: N-Nitroso-N-Desmethyl Doxycycline

• English Alias: (4S,4aR,5S,5aR,6R,12aS)-3,5,10,12,12a-pentahydroxy-6-methyl-4-(methyl(nitroso)amino)-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

• CAS Number: None

• Molecular Formula: C₂₁H₂₁N₃O₉

• Molecular Weight: 459.41

Advantages

As a nitroso impurity of N-Desmethyl Doxycycline, this compound has the following advantages:

• Well-defined with multiple chiral centers: Contains (4S,4aR,5S,5aR,6R,12aS) hexachiral tetracene core, pentahydroxy substituents, 4-methyl(nitroso)amino, and 2-carboxamide. Unlike N-desmethyl doxycycline, its nitrosoamide polarity and tetracene hydrophobicity create significant differences, enabling precise differentiation via HPLC/ion-pair chromatography as a specific marker;

• High stability and traceability: Rigid tetracene structure and stability of hydroxyls/nitrosoamide ensure stability under dark, low-temperature conditions. As a derivative from amine nitrosation during storage/degradation, it directly reflects amino stability and nitrite exposure, improving impurity tracing accuracy;

• High detection sensitivity: Tetracene conjugation shows strong UV absorption (260-300nm), combined with m/z 460 [M+H]⁺ enabling ppb-level analysis via LC-MS, compatible with tetracycline nitroso impurity systems.

Applications

• Pharmaceutical quality control: Used as an impurity reference standard to quantify N-Nitroso-N-Desmethyl Doxycycline 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;

• Degradation pathway analysis: Identifying 4-amino nitrosation as a key degradation route to guide formulation improvements (e.g., antioxidant addition).

Background Description

N-Desmethyl doxycycline, a doxycycline metabolite, contains a 4-methylamino group that may undergo nitrosation upon exposure to nitrous acid (e.g., from nitrate reduction), forming 4-methyl(nitroso)amino derivatives like N-Nitroso-N-Desmethyl Doxycycline. Due to potential genotoxicity, nitroso impurities are strictly regulated, and their residues may affect doxycycline safety, making detection and control critical for quality assurance.

Research Status

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 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, chromosome aberration) 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!

WhatsAPP: +86 17386083646
E-mail: anna@molcoo.com