Journal of Pharmaceutical and Biomedical Analysis, volume 118, pages 235-241
Isolation and characterization of a tadalafil analogue, N -cyclopentyl nortadalafil in health supplement
Yimin Xu
1, 2
,
Chee Leong Kee
2
,
Xiaowei Ge
2
,
Min Yong Low
2
,
Hwee-Ling Koh
3
2
Pharmaceutical Laboratory, Applied Sciences Group, Health Sciences Authority, 11 Outram Road, Singapore 160978, Singapore
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Publication type: Journal Article
Publication date: 2016-01-01
scimago Q2
wos Q2
SJR: 0.584
CiteScore: 6.7
Impact factor: 3.1
ISSN: 07317085, 1873264X
Drug Discovery
Spectroscopy
Pharmaceutical Science
Clinical Biochemistry
Analytical Chemistry
Abstract
A tadalafil analogue was detected for the first time during the screening of a health supplement for undeclared sexual enhancement drugs. The compound had been isolated and purified by preparative high-pressure liquid chromatography (HPLC). Its chemical structure was elucidated using high-resolution mass spectrometry (HRMS), electrospray ionization tandem mass spectrometry (ESI-MS/MS) and nuclear magnetic resonance (NMR) spectroscopy. The compound had a protonated molecular ion at m/z 444 with a chemical formula of C26H25N3O4. The data obtained from the MS analysis of the compound suggested that the N-methyl group on the piperazinedione moiety of tadalafil was substituted with a -C5H9 group. Analysis using NMR was performed and the -C5H9 group was characterized as a cyclopentyl moiety. The analogue was named N-cyclopentyl nortadalafil.
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