Cyclobenzaprine USP Related Compound A

Details:

Cyclobenzaprine USP Related Compound A; 18029-54-4

Product Information

• Product Code：C140001

• English Name：Cyclobenzaprine USP Related Compound A

• English Alias：5-(3-(dimethylamino)propyl)-5H-dibenzo[a,d][7]annulen-5-ol

• CAS No.：18029-54-4

• Molecular Formula：C??H??NO

• Molecular Weight：293.40

Advantages

• High-Purity Reference Standard：Confirmed by HPLC (≥99.0%), NMR (1H, 13C), HRMS, and elemental analysis, compliant with USP standards, suitable for Cyclobenzaprine impurity analysis and quality control.

• Stability Assurance：Stable for 36 months at -20℃ under light-protected, sealed storage; degradation rate <0.3% in methanol-water mixture within 6 months.

Applications

• USP Compliance Testing：Used for UPLC-MS/MS detection of USP Related Compound A in Cyclobenzaprine API and formulations, controlling content to meet USP pharmacopoeia standards (single impurity limit ≤0.1%).

• Process Optimization Research：Monitors impurity formation during Cyclobenzaprine synthesis, reducing generation by >40% by adjusting cyclization temperature (e.g., 80-90℃) and reaction time.

• Method Validation：Serves as a USP reference standard for developing impurity detection methods, verifying UPLC resolution (≥3.0) and LOD (0.01 ng/mL).

Background Description

Cyclobenzaprine, a skeletal muscle relaxant, is used to relieve muscle spasms. USP Related Compound A, as a process-related impurity of Cyclobenzaprine, may originate from hydroxylation side reactions during dibenzocycloheptene ring synthesis. Its hydroxyl and dimethylamino groups may affect drug stability and efficacy. Due to specific control requirements in the USP, studying this impurity is crucial for ensuring Cyclobenzaprine quality.

Research Status

• Detection Technology：UPLC-MS/MS with C18 column (1.7μm) and 0.1% formic acid-acetonitrile gradient elution achieves separation within 6 minutes, with LOD of 0.005 ng/mL meeting USP pharmacopoeia trace analysis requirements.

• Formation Mechanism：Formed by hydration of 5-(3-(dimethylamino)propyl)-5H-dibenzo[a,d][7]annulene under acidic conditions (e.g., acetic acid/water system); optimizing reaction pH and solvent polarity inhibits side reactions.

• Safety Evaluation：In vitro cytotoxicity shows IC?? of 195.3 μM against C2C12 muscle cells (Cyclobenzaprine IC??=12.6 μM), with lower toxicity than the main drug but requiring strict content control. Long-term stability testing is ongoing to monitor degradation under different humidity, light, and temperature conditions.