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The metabolism of N-benzylpiperazine (BZP), a recently scheduled designer drug, in the rat has been studied by analyzing its urinary metabolites. p-Hydroxy-BZP (p-OH-BZP) was unequivocally identified as the main metabolite along with a minor metabolite m-hydroxy-BZP (m-OH-BZP), using gas chromatography-mass spectrometry and high-performance liquid chromatography-electrospray ionization mass spectrometry (LC-ESI MS). The time-course excretion profiles of BZP, p-OH-BZP, and m-OH-BZP in the rats were investigated after a single intraperitoneal dosing of 5 mg/kg BZP, by using an optimized analytical procedure that combines solid-phase extraction and LC-ESI MS determination. The cumulative amounts excreted within the first 48 h were approximately 25% for p-OH-BZP and 2% for m-OH-BZP, whereas 6.7% dose of the parent drug BZP was excreted unchanged within 36 h post-dosing. The concentration ratio of p-OH-BZP to m-OH-BZP was 11.6 in the first 4 h, but it increased to 22.7 in 48 h with the elapsed time post-dosing. Most of p-OH-BZP was excreted in urine within approximately 36 h post-dosing, with approximately 50% appearing as the glucuronide conjugate. The present results suggest that p-OH-BZP is the most relevant metabolite to be detected for the proof of BZP intake in the forensic and clinical analysis of human urine.

Metabolism and the Urinary Excretion Profile of the Recently Scheduled Designer Drug N-Benzylpiperazine (BZP) in the Rat