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The accurate assessment of racemic pharmaceuticals requires enantioselective analytical methods. This study presents the development and validation of an enantioselective liquid chromatography with a fluorescence detection method for the concomitant quantification of the enantiomers of tramadol and their metabolites, N-desmethyltramadol and O-desmethyltramadol, in wastewater samples. Optimized conditions were achieved using a Lux Cellulose-4 column 150 Chi 4.6 mm, 3 mu m isocratic elution, and 0.1% diethylamine in hexane and ethanol (96: 4, v/v) at 0.7 mL min 1. The samples were extracted using 150 mg Oasis (R) mixed-mode cation exchange (MCX) cartridges. The method was validated using a synthetic effluent of a laboratory-scale aerobic granular sludge sequencing batch reactor. The method demonstrated to be selective, accurate, and linear (r(2) > 0.99) over the range of 56 ng L (-1) to 392 ng L (-1). The detection and the quantification limits of each enantiomer were 8 ng L 1 and 28 ng L (-1) for tramadol and N-desmethyltramadol, and 20 ng L (-1) And 56 ng L- 1 for O-desmethyltramadol. The feasibility of the method was demonstrated in a screening study in influent and effluent samples from a wastewater treatment plant. The results demonstrated the occurrence of tramadol enantiomers up to 325.1 ng L (-1) and 357.9 ng L (-1), in the effluent and influent samples, respectively. Both metabolites were detected in influents and effluents.