Excretory Profile of 4-Bromo-2,5-dimethoxyphenethylamine (2C-B) in Rat.

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.…”

Identification of 2,5-dimethoxy-4-ethylthiophenethylamine and its metabolites in the urine of rats by gas chromatography–mass spectrometry

“…These compounds are often referred to as "designer drugs" because all are considered potent stimulants of the central nervous system, but contain slightly different functional groups in their chemical structure. 2C-T-2 is a ringsubstituted phenethylamine, possesses psychoactive properties [1] and similar to 2C-B [4][5][6][7], but little information is available concerning its detection and metabolic fate.…”

A model system for prediction of the in vivo metabolism of designer drugs using three-dimensional culture of rat and human hepatocytes

“…The 2C-B metabolite profiles in TESTLIVER-rat and TESTLIVER-human culture media after incubation are shown in Table 2 were also found. According to our previous report [15], the main in vivo metabolite of 2C-B in rat urine was 5-OH-NAc-2C-B followed by 2-OH-NAc-2C-B and OH-2C-Bs, whereas excretion of 2C-B-CBA and 2C-B-ALC was relatively minor. Although percent distribution of the metabolites obtained from the TESTLIVERrat system after 48 h incubation was quantitatively different from that obtained from rat in vivo experiments, the same metabolites could be detected for both the new in vitro system and the conventional in vivo experiments ( Table 2).…”

“…7. 2C-T-7 is mainly metabolized by sulfoxidation, sulfone formation, hydroxylation of the S-propyl group, N-acetylation, and S-depropylation followed by Data expressed as mean ± standard deviation of six determinations (two lots, three bundles for each lot) a Data from Kanamori et al [15] b S-methylation [12]. 2C-T-7 metabolite profiles in TEST-LIVER-rat and TESTLIVER-human are shown in Table 4.…”