RESUMEN
A new sildenafil analogue, propoxyphenyl isobutyl aildenafil has been found in trace quantity from one health supplement. It has been purified by preparative high performance liquid chromatography (HPLC). The structural elucidation of this compound has been carried out using high-resolution Orbitrap mass spectrometry under two fragmentation modes, namely High energy Collision Dissolution (HCD) and Collision Induced Dissolution (CID). Under MS(3) experiments and CID mode, the isobutyl-bonded fragments of propoxyphenyl isobutyl aildenafil at m/z 313 and 297 have been compared with the reference ions derived from isobutyl sildenafil. The accurate mass measurement of each product ions has been carried out with the aid of Mass Frontier software (version 5.0). The mass error of all product ions is not more than 5.0ppm.
Asunto(s)
Suplementos Dietéticos/análisis , Piperazinas/química , Sulfonas/química , Cromatografía Líquida de Alta Presión/métodos , Contaminación de Medicamentos , Iones/química , Espectrometría de Masas/métodosRESUMEN
Two unknown compounds are detected and isolated from health supplements for the enhancement of sexual function. The structures of the unknown compounds are elucidated using high-resolution MS, ESI-MS/MS, NMR, UV and IR. One compound is identified as an analogue of sildenafil in which the oxygen atom is substituted with a sulfur atom in the pyrazolopyrimidine moiety, and an ethyl group instead of a methyl group is attached to the piperazinyl nitrogen. Hence, this compound is named thiohomosildenafil. Another compound is also a sildenafil analogue in which the oxygen atom is substituted with a sulfur atom in the pyrazolopyrimidine moiety. This compound is named thiosildenafil. Both the two compounds are first detected in health supplements. The UV, IR and completely assigned NMR data of thiohomosildenafil and thiosildenafil are first reported.
Asunto(s)
Suplementos Dietéticos/análisis , Contaminación de Alimentos , Inhibidores de Fosfodiesterasa/análisis , Inhibidores de Fosfodiesterasa/aislamiento & purificación , Piperazinas/análisis , Piperazinas/aislamiento & purificación , Sulfonas/análisis , Sulfonas/aislamiento & purificación , Humanos , Espectroscopía de Resonancia Magnética , Masculino , Espectrometría de Masas , Estructura Molecular , Inhibidores de Fosfodiesterasa/química , Piperazinas/química , Purinas/análisis , Purinas/química , Purinas/aislamiento & purificación , Citrato de Sildenafil , Espectrometría de Masa por Ionización de Electrospray , Espectrofotometría Infrarroja , Espectrofotometría Ultravioleta , Sulfonas/química , Espectrometría de Masas en TándemRESUMEN
A sample labeled to be a natural herbal supplement for the enhancement of sexual function, was sent to Health Sciences Authority (HSA) of Singapore for testing. An unknown compound was detected and isolated from the product. The structure of the unknown compound was identified using LC-UV, high-resolution MS, ESI-MS/MS, IR, and NMR. The compound was characterized as a phosphodiesterase-5 (PDE-5) inhibitor, benzamidenafil. This is the first report of benzamidenafil, representing a new class of PDE-5 inhibitors, as an adulterant of a dietary supplement.