Sakamoto Miho, Moriyasu Takako, Minowa Keiko, Kishimoto Kiyoko, Kadoi Hideo, Hamano Tomoko, Fukaya Haruhiko
Tokyo Metropolitan Institute of Public Health, Department of Pharmaceutical Sciences, 24-1 Hyakunincho 3-chome, Shinjuku-ku, Tokyo 169-0073, Japan.
J AOAC Int. 2012 Jul-Aug;95(4):1048-52. doi: 10.5740/jaoacint.11-235.
A sildenafil-related compound was detected in a dietary supplement marketed as an aphrodisiac. The compound was detected during analysis of the dietary supplement using LC-UV and LC/electrospray ionization-MS. The structure of the compound was established using high resolution MS, NMR spectrometry, and X-ray crystal structure analysis. The compound was identified as 5-(5-((3,5-dimethylpiperazin-1-yl)sulfonyl)-2-ethoxyphenyl)-l-methyl-7-((1-methyl-4-nitro-1H-imidazol-5-yl)thio)-3-propyl-1H-pyrazolo[4,3-d] pyrimidine. Based on this structure, the compound was named nitroprodenafil. The dietary supplement was found to contain 90 mg nitroprodenafil/capsule. This article describes the structural characterization of a new sildenafil-related compound. The compound was detected during analysis of a dietary supplement using LC-UV and LC/electrospray ionization (ESI)-MS. The structure was established using high resolution MS (HRMS), NMR spectrometry, and X-ray crystal structure analysis. The structures of methisosildenafil, thiomethisosildenafil, and this new analog, named nitroprodenafil (21), are shown in Figure 1. In the Demizu et al. report, the compound is named mutaprodenafil instead ofnitroprodenafil. Considering the naming right, the authors of this paper think the use of mutaprodenafil is appropriate as the compound name, although nitroprodenafil is used.
在一种作为壮阳药销售的膳食补充剂中检测到一种与西地那非相关的化合物。在使用液相色谱 - 紫外（LC - UV）和液相色谱/电喷雾电离质谱（LC/ESI - MS）对该膳食补充剂进行分析时检测到了该化合物。使用高分辨率质谱、核磁共振光谱和X射线晶体结构分析确定了该化合物的结构。该化合物被鉴定为5 - (5 - ((3,5 - 二甲基哌嗪 - 1 - 基)磺酰基)-2 - 乙氧基苯基)-1 - 甲基 - 7 - ((1 - 甲基 - 4 - 硝基 - 1H - 咪唑 - 5 - 基)硫代)-3 - 丙基 - 1H - 吡唑并[4,3 - d]嘧啶。基于此结构，该化合物被命名为硝基伐地那非。发现该膳食补充剂每粒胶囊含有90毫克硝基伐地那非。本文描述了一种新的与西地那非相关化合物的结构表征。在使用LC - UV和LC/电喷雾电离（ESI） - MS对一种膳食补充剂进行分析时检测到了该化合物。使用高分辨率质谱（HRMS）、核磁共振光谱和X射线晶体结构分析确定了其结构。甲磺酸异西地那非、硫代甲磺酸异西地那非以及这种名为硝基伐地那非（21）的新类似物的结构如图1所示。在出水区等人的报告中，该化合物被命名为变构伐地那非而非硝基伐地那非。考虑到命名权，本文作者认为尽管使用了硝基伐地那非，但使用变构伐地那非作为化合物名称是合适的。
