Isolation and identification of thiohomosildenafil and thiosildenafil in health supplements.
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.
Zou
Peng
P
Department of Pharmacy, Faculty of Science, National University of Singapore, Singapore.
Hou
Peiling
P
Oh
Sharon Sze-Yin
SS
Chong
Y M
YM
Bloodworth
Bosco Chen
BC
Low
Min-Yong
MY
Koh
Hwee-Ling
HL
D019587:Dietary Supplements / Q000032:analysis*; D005506:Food Contamination; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry; D015394:Molecular Structure; D010726:Phosphodiesterase Inhibitors / Q000032:analysis* / Q000737:chemistry / Q000302:isolation & purification*; D010879:Piperazines / Q000032:analysis* / Q000737:chemistry / Q000302:isolation & purification*; D011687:Purines / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification; D000068677:Sildenafil Citrate; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013450:Sulfones / Q000032:analysis* / Q000737:chemistry / Q000302:isolation & purification*; D053719:Tandem Mass Spectrometry
D010726:Phosphodiesterase Inhibitors; D010879:Piperazines; D011687:Purines; D013450:Sulfones; D000068677:Sildenafil Citrate