New designer drug N-(1-phenylcyclohexyl)-3-ethoxypropanamine (PCEPA): studies on its metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric techniques

Abstract

Studies are described on the metabolism and toxicological detection of the phencyclidine-derived designer drug N-(1-phenylcyclohexyl)-3-ethoxypropanamine (PCEPA) in rat urine using gas chromatographic/mass spectrometric techniques. The identified metabolites indicated that PCEPA was metabolized by N-dealkylation, O-deethylation partially followed by oxidation of the resulting alcohol to the corresponding carboxylic acid, hydroxylation of the cyclohexyl ring at different positions of PCEPA, N-dealkyl PCEPA, O-deethyl PCEPA, and of the corresponding carboxylic acids. Finally, aromatic hydroxylation of PCEPA, the corresponding carboxylic acids, and O-deethyl PCEPA, the latter partially followed by oxidation to the corresponding carboxylic acid and hydroxylation of the cyclohexyl ring could be observed. All metabolites were partially excreted in the conjugated form. The authors' systematic toxicological analysis (STA) procedure using full-scan GC/MS after acid hydrolysis, liquid-liquid extraction, and microwave-assisted acetylation allowed the detection in rat urine of an intake of a common drug users' dose of PCEPA. Assuming a similar metabolism in humans, the STA in human urine should be suitable as proof of intake of PCEPA.