26953-37-7

Usage

Uses

Used in Pharmaceutical Industry:
N-(2-AMINO-ETHYL)-2-(BENZYL-PHENYL-AMINO)-ACETAMIDE MALEATE is used as an impurity in the synthesis of Antazoline (A678405) for its role as a histamine H1 receptor blocker. This application is significant because it contributes to the development of antihistamine pharmaceuticals, which are crucial in treating various allergic reactions and conditions.
Application Reason:
The compound's involvement in the synthesis of Antazoline highlights its importance in the pharmaceutical industry. As a histamine H1 receptor blocker, Antazoline is effective in alleviating symptoms associated with histamine release, such as itching, redness, and swelling. This makes N-(2-AMINO-ETHYL)-2-(BENZYL-PHENYL-AMINO)-ACETAMIDE MALEATE a valuable component in the production of antihistamine medications.

Upstream product

• 107-15-3 ethylenediamine 
• 91-75-8 antazoline 

Relevant academic research and scientific papers

Synthesis and identification of the primary degradation product in a commercial ophthalmic formulation using NMR, MS, and a stability-indicating HPLC method for antazoline and naphazoline

HPLC analysis of an anti-infective ophthalmic solution (Albalon-A), containing the active drugs naphazoline and antazoline, revealed a degradation peak of unknown identity. To elucidate the identity of the degradant, the active drugs were each hydrolyzed by refluxing at high pH, and their respective hydrolysis products were isolated and spectrally characterized by NMR, FT-IR, and MS for conclusive structure elucidation. The degradant's identity was confirmed by HPLC-MS analysis of Albalon-A ophthalmic solution to be the antazoline hydrolysis product N-[(N- benzylanilino)acetyl]ethylenediamine (IV). A stability-indicating HPLC method was then developed which was able to resolve IV from the active drugs. This HPLC method was then validated for quantitating the active drugs and IV. Validation studies demonstrated linear UV response at 280 nm, recover >98%, good reproducibility, and a detection limit of 2 μg/mL IV. Overall, the data demonstrated that the HPLC method was quantitative and specific for antazoline, naphazoline, and IV. Analysis of an expired stability of the ophthalmic solution indicated the concentration of IV was 0.002% (w/v).

The influence of pH on the stability of antazoline: kinetic analysis

Degradation of the drug antazoline was studied in aqueous solutions by means of pH-rate profiling (pH 0-7.4). The novel approach of Runge-Kutta numerical integration in combination with multi-parameter optimisation was applied to UV-Vis spectral data to determine a valid kinetic model and kinetic parameters of the degradation process. The overall degradation mechanism was found to be dependent on the environmental pH. In the pH range of 3.0-7.4, the formation of the antazoline hydrolysis product (N-(2-aminoethyl)-2-(N-benzylanilino)acetamide) through three different pathways (acidic, non-catalysed, and semi-alkaline hydrolysis) was observed. In highly acidic media (pH 0-2), the degradation mechanism was found to be more complex. Although the same primary degradation product formed, a colourful (dark blue/violet) intermediate was also observed and further investigated by HPLC/TOF-MS.