Structure determination of new analogues of vardenafil and sildenafil in dietary supplements

H. J. Park, H. K. Jeong, M. I. Chang, M. H. Im, J. Y. Jeong, D. M. Choi, K. Park, M. K. Hong, J. Youm, S. B. Han, D. J. Kim, J. H. Park, S. W. Kwon

Research output: Contribution to journalArticle

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Abstract

New analogues of vardenafil and sildenafil illegally added to dietary supplements were detected by high-performance liquid chromatography (HPLC) analysis with a photodiode array detector (PDA). These compounds were isolated and their structures elucidated by mass spectrometry (MS), infrared (IR) spectroscopy, one- and two-dimensional nuclear magnetic resonance (NMR). One of the new analogues given the trivial name pseudovardenafil (compound 1) was structurally elucidated and shown to be 1-[[3-(1,4-dihydro-5-methyl-4-oxo-7-propylimidazo[5,1-f][1,2,4] triazin-2-yl)-4-ethoxyphenyl]sulfonyl]-piperidine. It was a vardenafil analogue isolated from a dietary supplement capsule Compared with vardenafil, the piperidine ring was substituted for the ethylpiperazine group. The second new analogue, trivially named hydroxyhongdenafil (compound 2), was separated from bulk powder used as a raw material for a dietary supplement. The piperazine and phenyl groups were connected through an acetyl group instead of a sulfonyl group, and hydroxyethylpiperazine was substituted for the methylpiperazine of sildenafil. It was structurally elucidated as 5-[2-ethoxy-5-[[4-(2-hydroxyethyl)-1-piperazinyl]acetyl]phenyl]-1, 4-dihydro-1-methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one.

Original languageEnglish (US)
Pages (from-to)122-129
Number of pages8
JournalFood Additives and Contaminants
Volume24
Issue number2
DOIs
StatePublished - Feb 2007

Fingerprint

Dietary supplements
Dietary Supplements
piperidines
dietary supplements
piperazine
High performance liquid chromatography
infrared spectroscopy
Photodiodes
Powders
detectors
Capsules
Names
Mass spectrometry
raw materials
nuclear magnetic resonance spectroscopy
Infrared spectroscopy
Mass Spectrometry
Spectrum Analysis
powders
Raw materials

ASJC Scopus subject areas

  • Food Science
  • Chemistry (miscellaneous)
  • Toxicology
  • Health, Toxicology and Mutagenesis

Cite this

Park, H. J., Jeong, H. K., Chang, M. I., Im, M. H., Jeong, J. Y., Choi, D. M., ... Kwon, S. W. (2007). Structure determination of new analogues of vardenafil and sildenafil in dietary supplements. Food Additives and Contaminants, 24(2), 122-129. https://doi.org/10.1080/02652030600983625

Structure determination of new analogues of vardenafil and sildenafil in dietary supplements. / Park, H. J.; Jeong, H. K.; Chang, M. I.; Im, M. H.; Jeong, J. Y.; Choi, D. M.; Park, K.; Hong, M. K.; Youm, J.; Han, S. B.; Kim, D. J.; Park, J. H.; Kwon, S. W.

In: Food Additives and Contaminants, Vol. 24, No. 2, 02.2007, p. 122-129.

Research output: Contribution to journalArticle

Park, HJ, Jeong, HK, Chang, MI, Im, MH, Jeong, JY, Choi, DM, Park, K, Hong, MK, Youm, J, Han, SB, Kim, DJ, Park, JH & Kwon, SW 2007, 'Structure determination of new analogues of vardenafil and sildenafil in dietary supplements', Food Additives and Contaminants, vol. 24, no. 2, pp. 122-129. https://doi.org/10.1080/02652030600983625
Park, H. J. ; Jeong, H. K. ; Chang, M. I. ; Im, M. H. ; Jeong, J. Y. ; Choi, D. M. ; Park, K. ; Hong, M. K. ; Youm, J. ; Han, S. B. ; Kim, D. J. ; Park, J. H. ; Kwon, S. W. / Structure determination of new analogues of vardenafil and sildenafil in dietary supplements. In: Food Additives and Contaminants. 2007 ; Vol. 24, No. 2. pp. 122-129.
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