Analysis of Phenethylamines and Tryptamines in Designer Drugs Using Gas Chromatographymass Spectrometry

Takahashi, Misako; Nagashima, Machiko; Suzuki, Jin; Seto, Takako; Yasuda, Ichirou; Yoshida, Takemi

doi:10.1248/jhs.54.89

Cited by 21 publications

(18 citation statements)

References 13 publications

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“…[66] 1 Formerly thioether. H NMR spectra have been reported for 2C-T-2 in CDCl3, [67] in CD3OD, [43] and in D2O [48,68] ; for 2C-T-4 in CDCl3, [69] and in D2O [48] ; for 2C-T-7 in CDCl3, [69] in CD3OD, [43] and in D2O. [48,70] We have not found 1 H NMR spectra reported for 2C-T.…”

Section: The 4-rs Family: 4-alkylsulfanyl-25-dimethoxyphenyl Patternmentioning

confidence: 89%

“…H NMR spectra have been reported for 2C-B in DMSO-d6, [29] in CDCl3, [15,40] in CD3OD, [41][42][43] and in D2O [31,32,42,44] ; for 2C-C in CDCl3 [45,46] and in D2O [31,46] ; for 2C-I in CDCl3 [43] and in D2O [31,32,47,48] ; for bk-2C-B in DMSO-d6 [38,39] and in CDCl3. [49] 1 H NMR spectra have been reported for 25B-NBOMe in DMSO-d6 [16,37] and in CDCl3 [15,50] ; for 25C-NBOMe in DMSO-d6, [37] in CDCl3, [51] and in CD3OD [16,52] ; for 25I-NBOMe in DMSO-d6, [16,37,53] in CDCl3, [15,[54][55][56] and in CD3OD [57] ; for 25I-NBOH in DMSO-d6 [15,16,37] ; for 25I-NBMD in DMSO-d6.…”

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confidence: 99%

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PeakAL: Protons I Have Known and Loved - Fifty Shades of Grey-Market Spectra

Chapman

Avanes²

2015

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Section: The 4-rs Family: 4-alkylsulfanyl-25-dimethoxyphenyl Patternmentioning

confidence: 89%

mentioning

confidence: 99%

PeakAL: Protons I Have Known and Loved - Fifty Shades of Grey-Market Spectra

Chapman

Avanes²

2015

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“…Como a estrutura molecular da droga é alterada, estas não são definidas como proscritas, burlando a legislação vigente. [9][10][11][12] As primeiras designer drugs que surgiram eram narcóticas derivadas da heroína. 13,14 Depois surgiram os derivados das feniletilaminas que incluem a 2-metil-amino-3,4-metileno-dioxi--propiofenona (metilona), N-metil-1-(1,3-benzodioxol-5-il)-2--butanamina (MBDB) e a 2,5-dimetoxi-4-iodo-feniletilamina (2C-I).…”

Section: Aspectos Biológicos E Analíticos Das Designer Drugsunclassified

“…A partir destes dados foi possível realizar uma determinação rápida para confirmação destas substâncias, mesmo em caso de isômeros de posição, combinando informações do espectro ultravioleta, espectro de massas e tempos de retenção nos cromatogramas. 63 …”

Section: Figura 7 Estruturas Químicas Dos Derivados Canabinoides Canunclassified

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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“…(9,67,68,69,76,77,80,89) Limits of detection of the various published GC-MS methods vary depending on the specific compound, the matrix and the ionization source, but the numbers for blood and urine mostly lie in the low ppb range, with the best techniques reporting 1-50 ng/mL. …”

Section: Confirmatory Techniquesmentioning

confidence: 99%

Comprehensive Forensic Toxicological Analysis of Designer Drugs

Swortwood¹

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When a positive result occurs, confirmatory methods, such as gas chromatography (GC) or liquid chromatography (LC) coupled with mass spectrometry (MS), are required for more sensitive and specific analyses. In recent years, the need to study the activities of these compounds in screening assays as well as to develop confirmatory techniques to detect them in biological specimens has been recognized. Severe intoxications and fatalities have been encountered with emerging designer drugs, presenting analytical challenges for detection and identification of such novel compounds. The first major task of this research was to evaluate the performance of commercially available immunoassays to determine if designer drugs were cross-reactive. The second major task was to develop and validate a confirmatory method, using LC-MS, to identify and quantify these designer drugs in biological specimens.vi Cross-reactivity towards the cathinone derivatives was found to be minimal.Several other phenethylamines demonstrated cross-reactivity at low concentrations, but results were consistent with those published by the assay manufacturer or as reported in the literature. Current immunoassay-based screening methods may not be ideal for presumptively identifying most designer drugs, including the "bath salts." For this reason, an LC-MS based confirmatory method was developed for 32 compounds, including eight cathinone derivatives, with limits of quantification in the range of 1-10 ng/mL. The method was fully validated for selectivity, matrix effects, stability, recovery, precision, and accuracy. In order to compare the screening and confirmatory techniques, several human specimens were analyzed to demonstrate the importance of using a specific analytical method, such as LC-MS, to detect designer drugs in serum as immunoassays lack cross-reactivity with the novel compounds. Overall, minimal crossreactivity was observed, highlighting the conclusion that these presumptive screens cannot detect many of the designer drugs and that a confirmatory technique, such as the LC-MS, is required for the comprehensive forensic toxicological analysis of designer drugs.vii

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Analysis of Phenethylamines and Tryptamines in Designer Drugs Using Gas Chromatographymass Spectrometry

Abstract: We developed a method for determining the following ten psychedelic phenethylamines and tryptamines by gas chromatography-mass spectrometry (GC-MS). The phenethylamines examined were 3,4,5-trimethoxyamphetamine (

Cited by 21 publications

References 13 publications

PeakAL: Protons I Have Known and Loved - Fifty Shades of Grey-Market Spectra

PeakAL: Protons I Have Known and Loved - Fifty Shades of Grey-Market Spectra

Designer drugs: aspectos analíticos e biológicos

Comprehensive Forensic Toxicological Analysis of Designer Drugs

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