A new analogue of sildenafil was discovered to have been added illegally to a functional food marketed for penile erectile dysfunction. The structure of the analogue was established by various NMR spectroscopic techniques (including DEPT, COSY, TOCSY, HMQC, HMBC). Because of the addition of a methylene group to sildenafil, the main ingredient of Viagra(R), it was given the name homosildenafil, and this has never been reported previously. An analytical method using HPLC was proposed. Homosildenafil was added as a new inspection item and other foods have since been discovered to contain it.

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