Isolation and structural elucidation of a new tadalafil analogue in health supplements: bisprenortadalafil

  • Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2016 Jun;33(6):945-52. doi: 10.1080/19440049.2016.1179134.
Ji Hyun Lee  1 ,  Han Na Park  1 ,  Bogonda Ganganna  2 ,  Ji Hye Jeong  1 ,  Sung-Kwan Park  1 ,  Jongkook Lee  2 ,  Sun Young Baek  1
Affiliations
  • 1. a Advanced Analysis Team, Toxicological Evaluation and Research Department , National Institute of Food and Drug Safety Evaluation, Ministry of Food and Drug Safety , Cheongju-si , Korea.
  • 2. b College of Pharmacy , Kangwon National University , Chuncheon , Korea.
PMID: 27167568 DOI: 10.1080/19440049.2016.1179134
Abstract

A new tadalafil analogue was found, along with nortadalafil, using HPLC-DAD during the inspection of a health product sold without official approval. The analogue was separated using a semi-preparative HPLC system and its structure was determined by a combination of mass spectrometry and NMR spectroscopy. The compound was identified as a tadalafil analogue in which the N-methyl group of tadalafil was replaced with a tadalafil precursor moiety. Nuclear Overhauser effect spectroscopy experiments suggested a cis-relationship between the substituents on a piperidine ring in the tadalafil moiety.

Keywords
PDE-5 inhibitor; Tadalafil analogue; bisprenortadalafil; dietary supplement; nortadalafil.
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