Identification of a new tadalafil analogue found in a dietary supplement

Eung-Sun LeeAdvanced Analysis Team, Toxicological Evaluation and Research Department, National Institute of Food and Drug Safety Evaluation, Korea Food & Drug Administration, Osong Health Technology Administration Complex, 187 Osongsaengmyeong2-ro, Yeonje-ri, Osongeup, Cheongwon-gun, Chungcheongbuk-do 363-700, Korea

Ji Won KimAdvanced Analysis Team, Toxicological Evaluation and Research Department, National Institute of Food and Drug Safety Evaluation, Korea Food & Drug Administration, Osong Health Technology Administration Complex, 187 Osongsaengmyeong2-ro, Yeonje-ri, Osongeup, Cheongwon-gun, Chungcheongbuk-do 363-700, Korea

Ji Hyun LeeAdvanced Analysis Team, Toxicological Evaluation and Research Department, National Institute of Food and Drug Safety Evaluation, Korea Food & Drug Administration, Osong Health Technology Administration Complex, 187 Osongsaengmyeong2-ro, Yeonje-ri, Osongeup, Cheongwon-gun, Chungcheongbuk-do 363-700, Korea

Kyoung Moon HanAdvanced Analysis Team, Toxicological Evaluation and Research Department, National Institute of Food and Drug Safety Evaluation, Korea Food & Drug Administration, Osong Health Technology Administration Complex, 187 Osongsaengmyeong2-ro, Yeonje-ri, Osongeup, Cheongwon-gun, Chungcheongbuk-do 363-700, Korea

Sooyeul ChoAdvanced Analysis Team, Toxicological Evaluation and Research Department, National Institute of Food and Drug Safety Evaluation, Korea Food & Drug Administration, Osong Health Technology Administration Complex, 187 Osongsaengmyeong2-ro, Yeonje-ri, Osongeup, Cheongwon-gun, Chungcheongbuk-do 363-700, Korea

Insun HwangAdvanced Analysis Team, Toxicological Evaluation and Research Department, National Institute of Food and Drug Safety Evaluation, Korea Food & Drug Administration, Osong Health Technology Administration Complex, 187 Osongsaengmyeong2-ro, Yeonje-ri, Osongeup, Cheongwon-gun, Chungcheongbuk-do 363-700, Korea

Soon Young HanAdvanced Analysis Team, Toxicological Evaluation and Research Department, National Institute of Food and Drug Safety Evaluation, Korea Food & Drug Administration, Osong Health Technology Administration Complex, 187 Osongsaengmyeong2-ro, Yeonje-ri, Osongeup, Cheongwon-gun, Chungcheongbuk-do 363-700, Korea

Kabyong ChaeAdvanced Analysis Team, Toxicological Evaluation and Research Department, National Institute of Food and Drug Safety Evaluation, Korea Food & Drug Administration, Osong Health Technology Administration Complex, 187 Osongsaengmyeong2-ro, Yeonje-ri, Osongeup, Cheongwon-gun, Chungcheongbuk-do 363-700, Korea

Jinho KimAdvanced Analysis Team, Toxicological Evaluation and Research Department, National Institute of Food and Drug Safety Evaluation, Korea Food & Drug Administration, Osong Health Technology Administration Complex, 187 Osongsaengmyeong2-ro, Yeonje-ri, Osongeup, Cheongwon-gun, Chungcheongbuk-do 363-700, KoreaCorrespondence[email protected]

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Abstract

A new tadalafil analogue, acetaminotadalafil, was detected by HPLC in a bulk powder that is being used as an ingredient formanufacturing dietary supplements. The analogue was isolated by semi-preparative HPLC. A chemical structure of the new compound was elucidated by HPLC, LC-quadrupole time-of-flight mass spectrometry (LC-Q-TOF/MS), nuclear magnetic resonance (NMR), infrared (IR) and circular dichroism (CD) spectroscopy. The compound was identified as an acetylatedcompound of aminotadalafil. The structure of the previous unknown compound was confirmed as (6R,12aR)-2-acetamino-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-pyrazino[1′,2′:1,6]pyrido[3,4-b]indole-1,4-dione and named as acetaminotadalafil.

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Acknowledgements

This work was supported by a grant (11181-KFDA-675) from the Korea Food and Drug Administration in 2011.

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Identification of a new tadalafil analogue found in a dietary supplement

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