Analysis of octopamine in human doping control samples

Abstract

The biogenic amine octopamine [4-(2-amino-1-hydroxyethyl)phenol] is prohibited in sports owing to its stimulating and performance-enhancing properties. Adverse analytical findings in athletes' doping control samples commonly result from surreptitious applications; however, the occurrence of octopamine in nutritional supplements and in selected invertebrates as well as the assumption that its N-methylated analog synephrine [4-(1-hydroxyethyl-2-methylamino)phenol, not banned by anti-doping authorities but currently monitored in prevalence studies) might be converted in-vivo into octopamine have necessitated a study to investigate the elimination of synephrine and octopamine present in over-the-counter products. Urine samples collected after administration of nutritional supplements containing octopamine and/or synephrine as well as urine samples collected after therapeutic application of octopamine- or synephrine-containing drugs were analyzed using a validated solid-phase extraction-based procedure employing a weak cation exchange resin and liquid chromatographic/tandem mass spectrometric detection with electrospray ionization and multiple reaction monitoring. In the case of therapeutic octopamine application, the urinary concentration of the target compound increased from baseline levels below the lower limit of detection to 142 µg/mL, while urine samples collected after synephrine as well as dietary supplement administration did not yield any evidence for elevated renal excretion of octopamine.

Separation of octopamine racemate on (R,S)-2-amino-1-phenylethanol imprinted polymer – Experimental and computational studies

“…The functional monomers: methacrylic acid (2), trifluoromethacrylic acid (4), itaconic acid (5), isopropenylbenzene (7), 2-hydroxyethyl methacrylate (8), and 2-(diethylamino)ethyl methacrylate (9) were from Sigma-Aldrich (Steinheim, Germany), acrylamide (6) and allylamine (10) were from Fluka (Steinheim, Germany), 4-vinylbenzoic acid (1), acrylic acid (3) were from Alfa Aesar (Karlsruhe, Germany). The cross-linker, ethylene glycol dimethacrylate was purchased from Sigma-Aldrich (Steinheim, Germany).…”

“…The monomers can be divided in three groups: acidic, 4-vinylbenzoic acid (1), methacrylic acid (2), acrylic acid (3), trifluoromethacrylic acid (4) or itaconic acid (5), neutral, acrylamide (6), isopropenylbenzene (7), 2-hydroxyethyl methacrylate (8) or 2-(diethylamino)ethyl methacrylate (9), and basic, allylamine (10). The polymerization process was carried out in methanol acting as the porogen, taking into account the solubility of all components.…”

“…The compound has been prohibited in elite sport since several adverse findings concerning octopamine have been reported during doping control analyses. Moreover, the N-methylated analog of octopamine-synephrine, which is not banned by anti-doping authorities, might be converted in vivo into octopamine [9].…”

Development and validation of an LC–MS/MS method for the quantification of ephedrines in urine

“…In anti-doping analysis ephedrines used to be quantified in urine by GC-NPD, GC-MS or HPLC-UV after preconcentrating the sample by liquid-liquid extraction (LLE) [3][4][5] or after an online clean-up [6]. The sensitivity of liquid chromatography coupled to mass spectrometry (LC-MS) and the compatibility of the system with the aqueous matrix of urine has allowed quantitative analysis of ephedrines without preconcentration step by direct injection [7,8]. The aim of this work is to develop and validate a quantitative method for the direct urinary detection of ephedrines by LC-MS/MS.…”

Stimulant Reduction Intervention using Dosed Exercise (STRIDE) - CTN 0037: Study protocol for a randomized controlled trial

“…Summarizing studies of the effect of exercise on neurotransmitters [37] conclude that exercise results in changes in synthesis and metabolism within central dopaminergic, noradrenergic, and serotonergic systems, all of which are implicated in addiction. Additional biological effects of exercise may include decreased reactivity to stress [38] and decreased use of substances as a way of coping with stress [39]. Exercise-induced improvements in self-efficacy [40,41] may be another mechanism for improving outcomes.…”