Identification of a new tadalafil analogue found in a dietary supplement

Lee, Eung-Sun; Kim, Ji Won; Lee, Ji Hyun; Han, Kyoung Moon; Cho, Soo-Yeul; Hwang, Insun; Han, Soon Young; Chae, Kabyong; Kim, Jin-Ho

doi:10.1080/19440049.2013.766766

Cited by 22 publications

(11 citation statements)

References 12 publications

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“…Adulteration is an exemplary repercussion of such laxity. Well documented are instances of diuretics, stimulants, anorectics, or oxidative uncouplers contained in weight loss supplements [60][61][62][63][64][65][66][67][68][69][70][71][72][73][74], steroids in performance enhancers [75][76][77][78][79][80], and phosphodiesterase 5 inhibitors contained within male enhancement products [72,74,[81][82][83][84][85][86][87][88][89][90][91][92][93]. At least nine people died in Sweden following exposure to Kratom adulterated with Odesmethyltramadol, a potent opioid analgesic.…”

Section: Supplement Regulationmentioning

confidence: 99%

Suspected Adulteration of Commercial Kratom Products with 7-Hydroxymitragynine

et al. 2016

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Introduction Kratom (Mitragyna speciosa), a plant native to Southeast Asia, has been used for centuries for its stimulant and opium-like effects. Mitragynine and 7-hydroxymitragynine, exclusive to M. speciosa, are the alkaloids primary responsible for Kratom's biologic and psychoactive profile, and likely contribute to its problematic use. We purchased several commercially available Kratom analogs for analysis and through our results, present evidence of probable adulteration with the highly potent and addictive plant alkaloid, 7-hydroxymitragynine. Methods A simple and sensitive LC-MS/MS method was developed for simultaneous quantification of mitragynine and 7-hydroxymitragynine in methanol extract of marketed Kratom supplements. Results We found multiple commercial Kratom products to have concentrations of 7-hydroxymitragynine that are substantially higher than those found in raw M. speciosa leaves. Conclusions We have found multiple packaged commercial Kratom products likely to contain artificially elevated concentrations of 7-hydroxymitragynine, the alkaloid responsible for M. speciosa's concerning mechanistic and side effect profile. This study describes a unique form of product adulteration, which stresses the importance of increased dietary supplement oversight of Kratom-containing supplements.

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Section: Supplement Regulationmentioning

confidence: 99%

Suspected Adulteration of Commercial Kratom Products with 7-Hydroxymitragynine

et al. 2016

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“…Since the identification of homosildenafil by Shin et al [7], there are 46 analogues being reported [5]. Recently, our laboratory found a new tadalafil analogue, acetaminotadalafil, in dietary supplement [8]. The consumption of these adulterated products could be harmful to consumers with various health risks.…”

Section: Introductionmentioning

confidence: 97%

Simultaneous determination of 38 phosphodiestrase-5 inhibitors in illicit erectile dysfunction products by liquid chromatography–electrospray ionization-tandem mass spectrometry

Lee

Han

et al. 2013

Journal of Pharmaceutical and Biomedical Analysis

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“…Several analogs of tadalafil have been reported in the literature . Aminotadalafil ( RR ‐ATDF) was first described in 2006 .…”

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confidence: 99%

Identification of N‐octylnortadalafil and its Stereoisomers in Dietary Supplements with Chiral Liquid Chromatography–Circular Dichroism

et al. 2016

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A direct chiral liquid chromatography-circular dichroism (LC-CD) method was developed for the simple and rapid identification of N-octylnortadalafil [(6R, 12aR)-6-(1,3-benzodioxol-5-yl)-2-octyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione; RR-OTDF] and its stereoisomers in dietary supplements. Samples were extracted with methanol. Compounds were then separated by chiral LC-CD using Chiralcel OD-RH (4.6 × 150 mm, 5 µm) with 5 mM ammonium formate (pH 3)/0.1% formic acid in acetonitrile (95:5, v/v) mixture solution (mobile phase A) and 0.1% formic acid in acetonitrile (mobile phase B). The isocratic elution used was mobile phase A / mobile phase B (3:7, v/v) at a flow rate of 1 ml/min. The column temperature was held at 30°C. RR-OTDF and its stereoisomers were separated within 20 min with the resolution factors being over 2.0. Using this method, RR-OTDF and (6R, 12aS)-6-(1,3-benzodioxol-5-yl)-2-octyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione were detected in a dietary supplement.

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Identification of a new tadalafil analogue found in a dietary supplement

Cited by 22 publications

References 12 publications

Suspected Adulteration of Commercial Kratom Products with 7-Hydroxymitragynine

Suspected Adulteration of Commercial Kratom Products with 7-Hydroxymitragynine

Simultaneous determination of 38 phosphodiestrase-5 inhibitors in illicit erectile dysfunction products by liquid chromatography–electrospray ionization-tandem mass spectrometry

Identification of N‐octylnortadalafil and its Stereoisomers in Dietary Supplements with Chiral Liquid Chromatography–Circular Dichroism

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