1-Benzhydryl-piperazine: Isolation, structure determination, and in silico studies for a novel potential narcotic agent detected in sports supplements

Adulteration of sports supplements poses significant health risks, necessitating stringent regulatory oversight. This study investigates deceptive practices by manufacturers, including concealment of formulations and manipulation of label information, impacting a wide demographic beyond elite athletes. Cinnarizine (CIN), and its degradation product, 1-benzhydryl-piperazine (BHP), which has amphetamine-like effects, are detected for the first time in 8 out of 41 sports supplements. An HPTLC method was developed to quantify CIN, and validated with specificity, linearity, the limit of detection (LOD), the limit of quantification (LOQ), accuracy, and precision studies. The linear range was between 50–800 ng spot−1. LOD and LOQ were 15 and 50 ng spot−1, respectively. The average recovery was calculated as 88.32 %, and %RSD values were less than 4 %. CIN’s degradation products were detected using GC-MS. CIN's decomposition into BHP also was confirmed via NMR analysis. Molecular docking studies revealed BHP's superior binding affinity and stability compared to 1-benzyl-piperazine (BZP), a prohibited narcotic agent, for dopamine and serotonin receptors, indicating potent psychoactive effects. Molecular dynamics simulations further elucidated interaction patterns, highlighting BHP's robust binding and potential for abuse, necessitating regulatory scrutiny and potential reevaluation of its legal status. It is also the first in silico study to compare BHP with BZP in terms of receptor interactions, which makes it pioneering. This study emphasizes the critical need for regulatory vigilance in the sports supplement industry to ensure consumer safety. Methodologies developed here for detecting adulterants provide foundational tools for future research aimed at enhancing public health protections against adulterated supplements. Regulatory collaboration and enhanced quality controls are essential to mitigate risks associated with deceptive practices and ensure the well-being of consumers. [Display omitted] •Adulteration in sports supplements is an increasing problem.•Cinnarizine is detected as an adulterant in sports supplements for the first time.•HPTLC was used to quantify cinnarizine, and its by-products were confirmed by GC-MS.•BHP’s affinity was studied for the interpretation as a potential narcotic agent.