Reepmeyer John C, D'Avignon D André
U.S. Food and Drug Administration, Division of Pharmaceutical Analysis, St. Louis, MO 63101, USA.
J AOAC Int. 2009 Sep-Oct;92(5):1336-42.
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 HPLCIMS, 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.
在一种作为壮阳药销售的草本膳食补充剂中检测到一种与西地那非相关的化合物。该化合物被鉴定为西地那非的类似物，其中西地那非嘧啶环中的羰基被硫羰基取代，哌嗪环上的甲基被羟乙基取代。基于此结构，该化合物被命名为硫羟高西地那非。使用高效液相色谱 - 质谱联用仪（HPLC - MS）、紫外光谱法、电喷雾电离 - 串联质谱法（ESI - MS/MS）、核磁共振光谱法以及水解过程确定了该化合物的结构。水解的一个关键产物是1 - （2 - 羟乙基） - 哌嗪；该产物的鉴定确定了化合物的胺部分。水解的另一个关键产物是羟高西地那非，它是由硫羰基水解为羰基（C = S → C = O）产生的。羟高西地那非在膳食补充剂中作为次要成分被检测到。
