TY - JOUR
T1 - 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
AU - Reepmeyer, John C.
AU - D'avignon, D. André
N1 - Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.
PY - 2009
Y1 - 2009
N2 - 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.
AB - 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.
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U2 - 10.1093/jaoac/92.5.1336
DO - 10.1093/jaoac/92.5.1336
M3 - Article
C2 - 19916370
AN - SCOPUS:70449377664
SN - 1060-3271
VL - 92
SP - 1336
EP - 1342
JO - Journal of AOAC International
JF - Journal of AOAC International
IS - 5
ER -