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☆

Theobald, Denis S.; Maurer, Hans H.

doi:10.1016/j.jchromb.2006.03.001

Cited by 40 publications

(29 citation statements)

References 41 publications

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“…This can be explained by formation of a mesomerically stabilized double bond or radical system after a loss of the acetamide part. Such fragmentation patterns have already been described for 2C-E [21]. Possible N-acetyl conjugates, described for other 2Cs [11], could of course not be differentiated from the chemically acetylated ones but were identified by LC-HR-MS n in the underivatized samples as described below.…”

Section: Identification Of the Phase I Metabolites By Gc-msmentioning

confidence: 64%

“…The postulated structures were deduced from the fragments detected in the EI mode, which were interpreted in correlation to that of the parent compound, other phenethylamines [21], and general Fig. 3 a Reconstructed GC-MS ion chromatograms recorded in human urine, indicating the spectra of the corresponding 2C-P metabolites (numbering according to Fig.…”

Section: Identification Of the Phase I Metabolites By Gc-msmentioning

confidence: 99%

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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

et al. 2014

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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.

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Section: Identification Of the Phase I Metabolites By Gc-msmentioning

confidence: 64%

Section: Identification Of the Phase I Metabolites By Gc-msmentioning

confidence: 99%

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

et al. 2014

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“…The majority of the drug undergoes a combination of O ‐demethylation, N ‐acetylation, deamination with oxidation to the corresponding acid, or reduction to the alcohol. Transformative pathways for 2C‐I and 2C‐E are not dissimilar, and in general, the O ‐demethylation of methoxy groups, beta‐oxidation of the alkyl side chain, and oxidative deamination can be likened to mescaline. In rat studies, the 2C‐T series may undergo combinations of N ‐acetylation, O ‐demethylation, sulfoxidation, S ‐dealkylation and S ‐methylation, and hydroxylation and demethylation .…”

Section: Dose and Duration Of Action Of 2c 2c‐t And Do‐series Drugsmentioning

confidence: 99%

Designer Psychostimulants in Urine by Liquid Chromatography–Tandem Mass Spectrometry,

Kerrigan

Mott

Jatzlau

et al. 2013

Journal of Forensic Sciences

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Designer psychostimulants are known by recreational drug users to produce a complex array of adrenergic and hallucinogenic effects. Many of these drugs are not targeted during routine toxicology testing and as a consequence, they are rarely reported. The purpose of this study was to develop a procedure for the detection of 15 psychostimulants in urine using liquid chromatography-tandem mass spectrometry (LC-MS/MS), specifically 2,5-dimethoxy-4-bromophenethylamine (2C-B), 2,5-dimethoxy-4-chlorophenethylamine (2C-C), 2,5-dimethoxy-4-methylphenethylamine (2C-D), 2,5-dimethoxy-4-ethylphenethylamine (2C-E), 2,5-dimethoxyphenethylamine (2C-H), 2,5-dimethoxy-4-iodophenethylamine (2C-I), 2,5-dimethoxy-4-ethylthiophenethylamine (2C-T-2), 2,5-dimethoxy-4-isopropylthiophenethylamine (2C-T-4), 2,5-dimethoxy-4-propylthiophenethylamine (2C-T-7), 2,5-dimethoxy-4-bromoamphetamine (DOB), 2,5-dimethoxy-4-chloroamphetamine (DOC), 2,5-dimethoxy-4-ethylamphetamine (DOET), 2,5-dimethoxy-4-iodoamphetamine (DOI), 2,5-dimethoxy-4-methylamphetamine (DOM), and 4-methylthioamphetamine (4-MTA). Analytical recoveries using solid-phase extraction were 64-92% and the limit of detection was 0.5 ng/mL for all drugs except 2C-B (1 ng/mL). The assay was evaluated in terms of analytical recovery, precision, accuracy, linearity, matrix effect, and interferences. The technique allows for the simultaneous detection of 15 psychostimulants at sub-ng/mL concentrations.

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“…Alguns estudos têm sido publicados sobre o processo de biotransformação de substâncias psicoativas, principalmente das feniletilaminas. 50,51 Para a 2C-B, estudos investigaram o processo da biotransformação, procurando identificá-la qualitativa e quantitativamente em hepatócitos de ratos 52 e metabólitos na urina. 5,51,53,54 Foi publicado, também, o processo de biotransformação hepático da 2C-B em seis diferentes espécies, incluindo humanos e camundongos.…”

Section: Derivados Anfetamínicosunclassified

Designer drugs: aspectos analíticos e biológicos

Bulcão¹,

Garcia²,

Limberger³

et al. 2012

Quím. Nova

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Recebido em 17/12/10; aceito em 12/7/11; publicado na web em 2/9/11 DESIGNER DRUGS: ANALYTICAL AND BIOLOGICAL ASPECTS. In the recent years, analytical toxicologists have been facing difficulties in detecting designer drugs due to the chemical modifications on the existing structures and the speed in which they are released into the market, requiring the development and improvement of specific and appropriate analytical methods. This work is a review of the literature which summarizes the characteristics of the drugs and the analytical validated methods using conventional and unconventional matrices currently used for correct identification and quantification of the following classes of emerging drugs of abuse: derivatives of opiates, amphetamines, tryptamines, piperazines and cannabinoids.Keywords: biological matrices; drug abuse; toxicology. INTRODUÇÃOAs chamadas designer drugs (drogas planejadas, ou seja, aná-logos estruturais) estão entre as drogas de abuso mais utilizadas no Ocidente. Seus efeitos psicotrópicos específicos, que fundamentam sua utilização como drogas de abuso, são descritos como capacidade aumentada da comunicabilidade, empatia e autoconhecimento, o que distingue esta classe de compostos das substâncias estimulantes e alucinógenas propriamente ditas, que produzem estados de euforia e agitação e, alucinações visuais e auditivas, respectivamente. 1,2A utilização de substâncias psicoativas é antiga na história da civilização, as primeiras experiências humanas ocorreram por meio do consumo de plantas. A partir do século XIX, o homem isolou princípios ativos vegetais como morfina, cocaína e efedrina. Porém, foi no final do século passado, com o surgimento das anfetaminas, que uma substância psicoativa foi totalmente sintetizada em laboratório. Com o aparecimento das drogas sintéticas, nos anos 80, ocorreu a popularização das designer drugs. Essas drogas têm como característica essencial o fato de terem sido modificadas em laboratório, com o intuito de potencializar ou criar efeitos psicoativos ou evitar efeitos indesejáveis, além de burlar a legislação vigente. Além disto, a disponibilidade e a diminuição do custo tecnológico permitem que tais drogas sejam sintetizadas com facilidade em laboratórios clandestinos domésticos. [3][4][5] Nos anos 90, com a popularização da internet, houve uma enorme divulgação e distribuição das designer drugs. 5,6 Entretanto, foi na primeira década do século XXI que o número de novos usuários de substâncias ilícitas aumentou de forma significativa, com relatos da apreensão de diversas designer drugs em todo o mundo. 7,8As designer drugs mais utilizadas são os compostos anfetamíni-cos, tais como 3,4-metileno-dioxi-anfetamina (MDA), 3,4-metilenodioxi-metanfetamina (MDMA, ecstasy), p-metoxi-anfetamina (PMA) e p-metoxi-metanfetamina (PMMA). No Brasil, o uso recreacional tem sido constatado em vários pacientes que buscam tratamento nas clínicas de reabilitação, além de apreensões destas drogas, sendo, portanto, de grande relevância sua correta identificação e/ou quantific...

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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☆

Cited by 40 publications

References 41 publications

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

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

Designer Psychostimulants in Urine by Liquid Chromatography–Tandem Mass Spectrometry,

Designer drugs: aspectos analíticos e biológicos

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