Voltammetric Oxidation of Drugs of Abuse II. Codeine and Metabolites

Garrido, Jorge; Delerue–Matos, Cristina; Borges, Fernanda; Macedo, T.R.A.; Oliveira-Brett, Ana Maria

doi:10.1002/elan.200302967

Cited by 43 publications

(27 citation statements)

References 30 publications

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“…In addition, it could be found in literature some studies involving compounds possessing similar functionalities that present a wave at similar potentials to that established for MDMA and MDA and that were also directly related to the oxidation of the aromatic ring [40,41].…”

Section: Electrochemical Oxidationmentioning

confidence: 64%

Electrochemical and spectroscopic characterisation of amphetamine-like drugs: Application to the screening of 3,4-methylenedioxymethamphetamine (MDMA) and its synthetic precursors

Milhazes

Martins

Uriarte

et al. 2007

Analytica Chimica Acta

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A complete physicochemical characterisation of MDMA and its synthetic precursors MDA, 3,4-methylenedioxybenzaldehyde (piperonal) and 3,4-methylenedioxy-␤-methyl-␤-nitrostyrene was carried out through voltammetric assays and Raman spectroscopy combined with theoretical (DFT) calculations. The former provided important analytical redox data, concluding that the oxidative mechanism of the N-demethylation of MDMA involves the removal of an electron from the amino-nitrogen atom, leading to the formation of a primary amine and an aldehyde. The vibrational spectroscopic experiments enable to afford a rapid and reliable detection of this type of compounds, since they yield characteristic spectral patterns that lead to an unequivocal identification.Moreover, the rational synthesis of the drug of abuse 3,4-methylenedioxymethamphetamine (MDMA or "ecstasy") from one of its most relevant precursors 3,4-methylene-dioxyamphetamine (MDA), is reported. In addition, several approaches for the N-methylation of MDA, a limiting synthetic step, were attempted and the overall yields compared.

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Section: Electrochemical Oxidationmentioning

confidence: 64%

Electrochemical and spectroscopic characterisation of amphetamine-like drugs: Application to the screening of 3,4-methylenedioxymethamphetamine (MDMA) and its synthetic precursors

Milhazes

Martins

Uriarte

et al. 2007

Analytica Chimica Acta

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“…3, E p ¼ þ 1.20 V, where the peak potential decreases as the pH increases (Fig. 2b), can easily be attributed to the oxidation of the tertiary amine group, by comparison with the voltammetric behavior of the heroin metabolites studied, in particular norheroin, as well as the behavior of other opiate analogues morphine and codeine (data not presented) [10]. The results obtained using a glassy carbon electrode are partially in agreement with those reported in the literature [9].…”

Section: Electrochemical Oxidationmentioning

confidence: 98%

“…Normorphine was prepared as described elsewhere [10]. Reagents used in the synthetic procedures were obtained from Sigma-Aldrich Quimica (Sintra, Portugal).…”

Section: Reagents and Solutionsmentioning

confidence: 99%

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Voltammetric Oxidation of Drugs of Abuse III. Heroin and Metabolites

Garrido¹,

Delerue–Matos²,

Borges

et al. 2004

Electroanalysis

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The oxidative behavior of heroin in aqueous solution is reported. In order to identify its oxidation peaks, several metabolites, 6-monoacetylmorphine, 3-monoacetylmorphine and norheroin, were synthesized and their electrochemical behavior studied using differential pulse voltammetry. The anodic waves observed for heroin correspond to the oxidation of the tertiary amine group and its follow-up product (secondary amine), and to the oxidation of the phenolic group obtained from hydrolysis, at alkaline pHs, of the 3-acetyl group. The results enabled a new oxidative mechanism for heroin to be proposed in which a secondary amine, norheroin, and an aldehyde are obtained. The voltammetric behavior of 6-monoacetylmorphine and morphine was found to be similar demonstrating that the presence of an acetyl substituent on the 6-hydroxy group does not have a relevant influence on the peak potential of the wave resulting from oxidation of the 3-phenolic group.

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“…The oxidation of phenethylamines as codeine, MDA and MDMA is complex 27,30,31 . MDA electrochemical studies are controversial as some authors show that MDA can undergo oxidation 30 while others stands the opposite 27 .…”

Section: Electrochemical Characterization Of 25b Nbome and 25imentioning

confidence: 99%

Rapid Screening Method for New Psychoactive Substances of Forensic Interest: Electrochemistry and Analytical Determination of Phenethylamines Derivatives (NBOMe) via Cyclic and Differential Pulse Voltammetry

2017

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ABSTRACT:The NBOMe derivatives are phenethylamines derived from the 2C class of hallucinogens. Only a few human pharmacologic studies have been conducted on these drugs and several cases of intoxication and deaths have been reported. Presently, NBOMe are not a part of the routine drugs-of-abuse screening procedure for many police forces and there are no rapid immunoassay screening tests that can detect the presence of those compounds. In this paper, the voltammetric behavior of 25B NBOMe and 25I NBOMe were investigated and their electroanalytical characteristics determined for the first time. A novel, fast and sensitive screening method for the identification of the two most common NBOMes (25B-NBOMe and 25I-NBOMe) in real samples is reported. The method uses the electrochemical oxidation of these molecules to produce an analytical signal that can be related to the NBOMe concentration with an average lower limit of quantitation of 0.01mg/mL for both of them. The method is selective enough to identify the two compounds individually, even given the great similarity in their structure.

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Voltammetric Oxidation of Drugs of Abuse II. Codeine and Metabolites

Cited by 43 publications

References 30 publications

Electrochemical and spectroscopic characterisation of amphetamine-like drugs: Application to the screening of 3,4-methylenedioxymethamphetamine (MDMA) and its synthetic precursors

Electrochemical and spectroscopic characterisation of amphetamine-like drugs: Application to the screening of 3,4-methylenedioxymethamphetamine (MDMA) and its synthetic precursors

Voltammetric Oxidation of Drugs of Abuse III. Heroin and Metabolites

Rapid Screening Method for New Psychoactive Substances of Forensic Interest: Electrochemistry and Analytical Determination of Phenethylamines Derivatives (NBOMe) via Cyclic and Differential Pulse Voltammetry

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