Structural elucidation of a tadalafil analogue found in a dietary supplement

A tadalafil analogue was detected in a dietary supplement marketed for tonic effect, along with hydroxyhomosildenafil and aminotadalafil. The tadalafil analogue was isolated by preparative thin layer chromatography (TLC) and its structure was elucidated using high-performance liquid chromatography (HPLC), liquid chromatography electrospray ionization-mass spectrometry (LC-ESI-MS), Fourier transform-ion cyclotron resonance-mass spectrometry (FT-ICR-MS) and nuclear magnetic resonance (NMR) spectroscopy. The compound was determined to be methyl-1-(1,3-benzodioxol-5-yl)-2-(chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate.