Metabolism of the designer drug 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in mice, after acute administration

Molecular and Cellular Mechanisms of Ecstasy-Induced Neurotoxicity: An Overview

“…This metabolite proved to be 100-fold more toxic than the parent drug MDMA when tested under the same experimental conditions [103]. The cytotoxic concentrations and effects of MDMA in the V79 fibroblasts were very similar to those observed previously in other cellular models including mouse hepatocytes [105,106]. The in vitro model used by Carmo and co-workers accounts only for the CYP2D6 catalyzed production of the oxidative metabolites.…”

Studies on the metabolism and toxicological detection of the designer drug 4-ethyl-2,5-dimethoxy-β-phenethylamine (2C-E) in rat urine using gas chromatographic–mass spectrometric techniques☆

“…The following metabolites in question could be identified: N-acetyl-2C-E (1), trifluoroacetylated 2C-E (21), N-acetyl-4-ethyltrifluoroacetoxy-methoxy-␤-phenethylamine isomer 1 (22), N-trifluoroacetyl-4-ethyl-trifluoroacetoxy-methoxy-␤-phenethylamine isomer 1 (23), N-acetyl-4-ethyl-trifluoroacetoxymethoxy-␤-phenethylamine isomer 2 (24), N-trifluoroacetyl-4-ethyl-trifluoroacetoxy-methoxy-␤-phenethylamine isomer 2 (25), N-acetyl-trifluoroacetoxy-methoxy-4-vinyl-␤-phenethylamine isomer 1 (26), N-acetyl-trifluoroacetoxy-methoxy-4-vinyl-␤-phenethylamine isomer 2 (27), N-trifluoroacetyl-4-(2 -trifluoroacetoxyethyl-)-trifluoroacetoxy-methoxy-␤-phenethylamine (28), N-acetyl-N-trifluoroacetyl-4-(2 -trifluoracetoxyethyl-)-2,5-dimethoxy-␤-phenethylamine (29), N-trifluoroacetyl-4-(2 -trifluoroacetoxyethyl)-2,5 -dimethoxy -␤ -phenethylamine (30), and N-acetyl-5-trifluoroacetoxy-2-methoxy-4-(2 -oxoethyl)-␤-phenethylamine (31). In the propionylated samples, the following compounds could be detected: N-acetyl-2,5 -dimethoxy-4-(1 -propionyloxyethyl) -␤ -phenethylamine (32) and N-acetyl-4-ethyl-2,5-dimethoxy-␤-propionyloxy-␤-phenethylamine (33). Only those compounds are shown, that allowed differentiation between metabolically N-acetylated metabolites and the free amines.…”

“…Furthermore, data on the metabolism are needed for toxicological risk assessment, because the metabolites may play a major role in the toxicity of a drug. Some studies have been published about the metabolism of psychoactive phenethylamines [25][26][27][28][29][30][31][32][33][34][35]. The aim of the study presented here was to identify the 2C-E metabolites in rat urine using GC-MS in the electron ionization (EI) and positive-ion chemical ionization (PICI) modes.…”

Studies on the toxicological detection of the designer drug 4-bromo-2,5-dimethoxy-β-phenethylamine (2C-B) in rat urine using gas chromatography–mass spectrometry

“…The metabolism of 2C-B has been extensively studied in rats [16][17][18], mice [19], and in hepatocytes from various species including humans [20,21]. Preliminary data are also available on excretion of 2C-B metabolites in human urine [22].…”