Biotransformation and detectability of the designer drug 2,5-dimethoxy-4-propylphenethylamine (2C-P) studied in urine by GC-MS, LC-MS n , and LC-high-resolution-MS n

Abstract

2,5-Dimethoxy-4-propylphenethylamine (2C-P) is a hallucinogenic designer drug of the phenethylamine class, the so-called 2Cs, named according to the ethyl spacer between the nitrogen and the aromatic ring. The aims of the present work were to identify the phases I and II metabolites of 2C-P. In addition, the detectability of 2C-P and its metabolites in urine as proof of an intake in clinical or forensic cases was tested. According to the identified metabolites, the following pathways were proposed: N-acetylation; deamination followed by reduction to the corresponding alcohol and oxidation to carbonic acid; mono- and bis-hydroxylation at different positions; mono- and bis-O-demethylation, followed by glucuronidation, sulfation, or both; and combination of these steps. Proof of an intake of a common user's dose of 2C-P was possible by both standard urine screening approaches, the GC-MS as well as the LC-MS(n) approach.

Diphenidine, a new psychoactive substance: metabolic fate elucidated with rat urine and human liver preparations and detectability in urine using GC‐MS, LC‐MSn, and LC‐HR‐MSn

“…Of course, depending on species differences, genetic variations, doses, and/or time after administration, diphenidine might also be detected and the panel of metabolites may vary. According to many former studies, combination of rat urine studies with incubations of new drugs with pHLM provides a tool for good predictions of phase I metabolites for detection in human urine.…”

“…The sample preparation was according to already published studies for lefetamine and its derivatives . A 2‐mL aliquot of urine was adjusted to pH 5.2 with acetic acid and incubated at 56°C for 1.5 h with 30 μL of a mixture (100 000 Fishman units/mL) of glucuronidase/arylsulfatase from Helix Pomatia L. Then, the urine sample was diluted with 2 mL of water, mixed and gradually loaded onto the cation exchange cartridge, which was preconditioned with 1 mL of methanol and 1 mL of water.…”

Mass spectrometric properties ofN-(2-methoxybenzyl)-2-(2,4,6-trimethoxyphenyl)ethanamine (2,4,6-TMPEA-NBOMe), a new representative of designer drugs of NBOMe series and derivatives thereof

“…), are the most studied and described in the literature. Most popular phenethylamines contain methoxy groups in positions 2 and 5 and different lipophilic substituents in position 4 in benzene ring (2C family) …”

“…Applying GC/MS to study amphetamines of 2C and NBOMe series (as well as of the metabolites thereof) and to ensure their reliable determination and identification, their acyl and alkyl derivatives are often obtained …”

High-resolution mass spectrometry in toxicology: current status and future perspectives

“…Some of these studies showed that the metabolism of rats was qualitatively comparable to that of humans as the rat metabolites could also be detected in authentic human urine from clinical or forensic case work Welter et al 2013Welter et al , 2015bMeyer et al 2013cMeyer et al , 2015Caspar et al 2015;Helfer et al 2015b;Wink et al 2015c).…”