Chromatographic separation of R/S-enantiomers of amphetamine and methamphetamine: Pathways of methamphetamine synthesis and detection in blood samples by qualitative enantioselective LC–MS/MS analysis

Maas, Alexandra; Losacker, Moritz; Heß, Cornelius

doi:10.1016/j.forsciint.2018.08.013

Cited by 22 publications

(13 citation statements)

References 27 publications

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“…Furthermore, consumption of very high doses or concomitant use of other drugs may lead to saturation of CYP2D6 so that metabolism is taken over by other (less stereoselective) enzymes. Illegal amphetamine is present exclusively in racemic form [ 4 , 43 , 57 ]. For forensic interpretation, therefore, the (additional) use of (S)-amphetamine-containing drugs must be excluded, as this medication would lead to an underestimation of the time difference to consumption.…”

Section: Discussionmentioning

confidence: 99%

“…Samples from individuals reporting consumption of pharmaceutical drugs containing (S)-amphetamine or (S)-amphetamine precursors (e.g., Attentin or Elvanse) or other enantiomeric compositions of amphetamine (e.g., Adderall) were excluded to prevent the data from being distorted. Cases positive for methamphetamine were also excluded, since amphetamine represents the main metabolite and this would therefore bias the results [ 4 ].…”

Section: Methodsmentioning

confidence: 99%

“…Amphetamine remains one of the most frequently abused drugs worldwide [ 1 ]. Intoxications with this stimulant represent one of the most common case groups and present difficult questions for toxicologists [ 2 , 3 , 4 ].…”

Section: Introductionmentioning

confidence: 99%

“…Amphetamine is a chiral molecule and exists in the enantiomeric forms (S)-amphetamine (d-(+)-amphetamine, dexamphetamine) and (R)-amphetamine (l-(-)-amphetamine, levoamphetamine). Analytical chiral separation is most commonly conducted via capillary electrophoresis (CE) [ 19 , 20 ], direct [ 4 , 21 ] and indirect high-performance liquid chromatography (HPLC) [ 22 , 23 ] and indirect gas chromatography (GC) [ 24 , 25 ].…”

Section: Introductionmentioning

confidence: 99%

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Enantioselective Quantification of Amphetamine and Metabolites in Serum Samples: Forensic Evaluation and Estimation of Consumption Time

et al. 2021

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In forensic toxicology, amphetamine intoxications represent one of the most common case groups and present difficult questions for toxicologists. Estimating the time of consumption and the current influence of the stimulant is particularly difficult when only total amphetamine concentrations are considered. Stereoselective analysis and the consideration of metabolites can provide valuable information to facilitate interpretation. An enantioselective liquid chromatography−tandem mass spectrometry (LC-MS/MS) method for detection of amphetamine, norephedrine and 4-hydroxyamphetamine was developed. Validation showed satisfactory selectivity, sensitivity, linearity (0.5–250 ng/mL), precision and accuracy for all enantiomers. The method was applied to a collective of 425 forensic serum samples and 30 serum samples from psychiatric inpatients stating their last time of amphetamine consumption. Norephedrine and 4-hydroxyamphetamine were detected more frequently at higher amphetamine concentrations and at lower amphetamine (R)/(S) concentration ratios, possibly indicating recent consumption. Mean (R)/(S) ratio of amphetamine was 1.14, whereas higher ratios (mean 1.36) were found for amphetamine concentrations below 100 ng/mL. The (R)/(S) ratios of psychiatric inpatients significantly correlated with the reported time intervals to last consumption. The use of amphetamine (R)/(S) ratios and the simultaneous detection of metabolites are promising factors that can facilitate estimation of consumption time and current impairment.

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Section: Discussionmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Enantioselective Quantification of Amphetamine and Metabolites in Serum Samples: Forensic Evaluation and Estimation of Consumption Time

et al. 2021

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“…Currently, multiple detection technologies have been established for MTA determination including high performance liquid chromatography (HPLC), liquid chromatography-mass spectrometry (LC-MS), liquid chromatography-tandem mass spectrometry (LC-MS-MS), gas chromatography (GC), gas chromatography-mass spectrometry (GC-MS), and gas chromatography/fourier transform infrared spectroscopy (GC/FTIR). [9][10][11][12][13][14] However, these methods involve some disadvantages, such as complicated operations, cumbersome sample pre-treatments and professional staff. Therefore, proposing new assays for simple and sensitive determination of MTA has become imperative.…”

Section: Introductionmentioning

confidence: 99%

Highly sensitive fluorescent aptasensor based on MoS2 nanosheets for one-step determination of methamphetamine

et al. 2022

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In this work, a simple and sensitive fluorescence aptasensor based on MoS2 nanosheets (MoS2-Ns) combined with fluorophore labeled aptamer (aptamer-FAM) for MTA determination in one step has been described. The aptamer-FAM can be spontaneously absorbed by the surface of MoS2-Ns to form an aptamer-FAM/MoS2-Ns sensing platform, resulting in the quenching of the fluorescence of aptamer-FAM largely. However, after introducing the target MTA, the fluorescence will be restored depending on the levels of MTA added. Such above reaction platform possesses a linear correlation between 5 and 2400 nM, with a detection limit of 2.3 nM (S/N=3). Moreover, the cross reactivity to ketamine, morphine and cocaine was little significant. Simultaneously, the assay was also successfully applied to recognize MTA in spiked human blood and urine, as well as in the real forensic identification samples obtained from the forensic case about MTA abuser.

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Determination of the enantiomeric composition of amphetamine, methamphetamine and 3,4‐methylendioxy‐N‐methylamphetamine (MDMA) in seized street drug samples from southern Germany

Losacker

Zörntlein

Schwarze

et al. 2021

Drug Testing and Analysis

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Amphetamine (speed), methamphetamine (crystal meth), and 3,4-methylenedioxy-Nmethylamphetamine (MDMA, ecstasy) represent the most frequently abused amphetamine-type stimulants (ATS). Differences in pharmacological potency and metabolism have been shown for the enantiomers of all three stimulants. Legal consequences in cases of drug possession may also differ according to the German law depending on the enantiomeric composition of the seized drug. Therefore, enantioselective monitoring of seized specimens is crucial for legal and forensic casework.Various kinds of samples of amphetamine (n = 143), MDMA (n = 94), and methamphetamine (n = 528) that were seized in southern Germany in 2019 and 2020 were analyzed for their chiral composition using different chromatographic methods.Whereas all samples of amphetamine and MDMA were racemic mixtures, the chiral composition of the methamphetamine specimens was diverse. Although the vast majority (n = 502) was present as (S)-methamphetamine, also specimens containing pure (R)-methamphetamine (n = 7) were found. Furthermore, few samples (n = 8) were of racemic nature or contained non-racemic mixtures of both enantiomers (n = 10).Because methamphetamine appears in varying enantiomeric compositions, any seizure should be analyzed using an enantioselective method. Amphetamine and MDMA, on the other hand, currently appear to be synthesized exclusively via racemic pathways and are not chirally purified. Nevertheless, regular monitoring of the chiral composition should be ensured.

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Chromatographic separation of R/S-enantiomers of amphetamine and methamphetamine: Pathways of methamphetamine synthesis and detection in blood samples by qualitative enantioselective LC–MS/MS analysis

Cited by 22 publications

References 27 publications

Enantioselective Quantification of Amphetamine and Metabolites in Serum Samples: Forensic Evaluation and Estimation of Consumption Time

Enantioselective Quantification of Amphetamine and Metabolites in Serum Samples: Forensic Evaluation and Estimation of Consumption Time

Highly sensitive fluorescent aptasensor based on MoS2 nanosheets for one-step determination of methamphetamine

Determination of the enantiomeric composition of amphetamine, methamphetamine and 3,4‐methylendioxy‐N‐methylamphetamine (MDMA) in seized street drug samples from southern Germany

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