Determination of designer doping agent – 2-ethylamino-1-phenylbutane – in dietary supplements and excretion study following single oral supplement dose

Self Cite

Higenamine (Norcoclaurine) is a very popular substance in Chinese medicine and is present in many plants. The substance may be also found in supplements or nutrients, consumption of which may result in violation of anti-doping rules. Higenamine is prohibited in sport at all times and included in Class S3 (β-2-agonists) of the World Anti-Doping Agency (WADA) 2017 Prohibited List. The presence of higenamine in urine samples at concentrations greater than or equal to 10 ng/mL constitutes an adverse analytical finding (AAF). This work presents a new metabolite of higenamine in urine sample which was identified by means of ultra performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS). Samples were prepared according to 2 protocols - a Dilute and Shoot (DaS) approach and a method involving acid hydrolysis and double liquid-liquid extraction (LLE). To meet the requirements typical for a confirmatory analysis, the screening procedure was further developed. In samples prepared by the DaS method, 2 peaks were observed; the earlier one was specific for higenamine and the later one unknown. MS scan analysis showed mass about 80 Da higher than that of higenamine. In turn, in samples prepared in accordance with the protocol involving hydrolysis, an increase in the area under peak for higenamine was observed, while the second peak was absent. It seems that the described strategy of detection of higenamine in urine avoids false negative results.

Section: Discussionmentioning

confidence: 99%

Analysis for higenamine in urine by means of ultra‐high‐performance liquid chromatography–tandem mass spectrometry: Interpretation of results

Grucza

Kwiatkowska

Kowalczyk

et al. 2017

Self Cite

“…In 2015, Wojtowicz et al . reported on the identification of a designer stimulant referred to as 2‐ethylamino‐1‐phenylbutane in both dietary supplements as well as an athlete's doping control sample . By means of administration studies and urine sample analysis by GC‐MS, elimination curves for the intact drug and one of its metabolites (2‐amino‐1‐phenylbutane) were obtained to support the interpretation of urinary concentrations occurring in the context of AAFs in doping controls.…”

Section: Stimulantsmentioning

confidence: 99%

Annual banned‐substance review: analytical approaches in human sports drug testing

Thevis

Kuuranne

Geyer

et al. 2017

There has been an immense amount of visibility of doping issues on the international stage over the past 12 months with the complexity of doping controls reiterated on various occasions. Hence, analytical test methods continuously being updated, expanded, and improved to provide specific, sensitive, and comprehensive test results in line with the World Anti-Doping Agency's (WADA) 2016 Prohibited List represent one of several critical cornerstones of doping controls. This enterprise necessitates expediting the (combined) exploitation of newly generated information on novel and/or superior target analytes for sports drug testing assays, drug elimination profiles, alternative test matrices, and recent advances in instrumental developments. This paper is a continuation of the series of annual banned-substance reviews appraising the literature published between October 2015 and September 2016 concerning human sports drug testing in the context of WADA's 2016 Prohibited List. Copyright © 2016 John Wiley & Sons, Ltd.

“…Similarly, Kobayashi et al . and Wojtowicz et al . investigated options to detect the newly identified phenethylamine derivative 2‐amino‐ N ‐ethyl‐1‐phenylbutane (2‐AEPB) in doping controls.…”

Section: Stimulantsmentioning

confidence: 99%

“…[203] The routinely applied GC-MS-based test method was assessed concerning its LOD for NN-DMPPA, which was determined at 30 ng/mL and, thus, fulfilling WADA MRPL criteria. Similarly, Kobayashi et al [204] and Wojtowicz et al [205] investigated options to detect the newly identified phenethylamine derivative 2-amino-N-ethyl-1-phenylbutane (2-AEPB) in doping controls. Following in vitro and in vivo studies, the intact compound and its desethylated analogue were identified as appropriate target analytes, enabling the unequivocal detection of the prohibited substance down to approximately 3-5 ng/mL using both LC-HRMS and GC-MS.…”

Section: Stimulantsmentioning

confidence: 99%

See 1 more Smart Citation

Annual banned‐substance review: analytical approaches in human sports drug testing

Thevis

Kuuranne

Walpurgis

et al. 2016

The aim of improving anti-doping efforts is predicated on several different pillars, including, amongst others, optimized analytical methods. These commonly result from exploiting most recent developments in analytical instrumentation as well as research data on elite athletes' physiology in general, and pharmacology, metabolism, elimination, and downstream effects of prohibited substances and methods of doping, in particular. The need for frequent and adequate adaptations of sports drug testing procedures has been incessant, largely due to the uninterrupted emergence of new chemical entities but also due to the apparent use of established or even obsolete drugs for reasons other than therapeutic means, such as assumed beneficial effects on endurance, strength, and regeneration capacities. Continuing the series of annual banned-substance reviews, literature concerning human sports drug testing published between October 2014 and September 2015 is summarized and reviewed in reference to the content of the 2015 Prohibited List as issued by the World Anti-Doping Agency (WADA), with particular emphasis on analytical approaches and their contribution to enhanced doping controls.