Use of a hydrolytic procedure and spectrometric methods in the structure elucidation of a thiocarbonyl analogue of sildenafil detected as an adulterant in an over-the-counter herbal aphrodisiac

John C. Reepmeyer, D. André D'avignon

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

A sildenafil-related compound was detected in an herbal dietary supplement marketed as an aphrodisiac. The compound was identified as an analogue of sildenafil in which the carbonyl group in the pyrimidine ring of sildenafil was substituted with a thiocarbonyl group, and the methyl group on the piperazine ring was substituted with a hydroxyethyl group. Based on this structure, the compound was named thiohydroxyhomosildenafil. The structure of the compound was established using HPLC/MS, UV spectrometry, electrospray ionization-MS/MS, NMR spectrometry, and a hydrolytic process. One key product of hydrolysis was 1-(2-hydroxyethyl)-piperazine; the identification of this product defined the amine portion of the compound. Another key product of hydrolysis was hydroxyhomosildenafil, generated by hydrolysis of the thiocarbonyl group to a carbonyl group (C = S → C = O). Hydroxyhomosildenafil was detected as a minor component in the dietary supplement.

Original languageEnglish (US)
Pages (from-to)1336-1342
Number of pages7
JournalJournal of AOAC International
Volume92
Issue number5
DOIs
StatePublished - 2009
Externally publishedYes

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