2-Methiopropamine, a thiophene analogue of methamphetamine: studies on its metabolism and detectability in the rat and human using GC-MS and LC-(HR)-MS techniques

@article{Welter20132MethiopropamineAT,
  title={2-Methiopropamine, a thiophene analogue of methamphetamine: studies on its metabolism and detectability in the rat and human using GC-MS and LC-(HR)-MS techniques},
  author={Jessica Welter and Markus R. Meyer and Ehud Wolf and Wolfgang Weinmann and Pierce V Kavanagh and Hans H Maurer},
  journal={Analytical and Bioanalytical Chemistry},
  year={2013},
  volume={405},
  pages={3125-3135}
}
Abstract2-Methiopropamine [1-(thiophen-2-yl)-2-methylaminopropane, 2-MPA], a thiophene analogue of methamphetamine, is available from online vendors selling “research chemicals.” The first samples were seized by the German police in 2011. As it is a recreational stimulant, its inclusion in routine drug screening protocols should be required. The aims of this study were to identify the phase I and II metabolites of 2-MPA in rat and human urine and to identify the human cytochrome-P450 (CYP… Expand
Ketamine-derived designer drug methoxetamine: metabolism including isoenzyme kinetics and toxicological detectability using GC-MS and LC-(HR-)MSn
TLDR
The enzyme kinetic studies showed that the initial metabolic step in humans, the N-deethylation, was catalyzed by CYP2B6 and CYP3A4, and both SUSAs using GC-MS or LC-MSn allowed monitoring an MXE intake in urine. Expand
Benzofuran analogues of amphetamine and methamphetamine: studies on the metabolism and toxicological analysis of 5-APB and 5-MAPB in urine and plasma using GC-MS and LC-(HR)-MSn techniques
Abstract5-APB (5-(2-aminopropyl)benzofuran) and its N-methyl derivative 5-MAPB (N-methyl-5-(2-aminopropyl)benzofuran) are analogues of amphetamine and methamphetamine, respectively, and belong to theExpand
Studies on the metabolism and toxicological detection of the new psychoactive designer drug 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine (25I-NBOMe) in human and rat urine using GC-MS, LC-MSn, and LC-HR-MS/MS
TLDR
25I-NBOMe was extensively metabolized and could be detected only by the LC-MS screening approaches, demonstrating that drug–drug interactions might occur in certain constellations. Expand
Elucidation of the metabolites of the novel psychoactive substance 4-methyl-N-ethyl-cathinone (4-MEC) in human urine and pooled liver microsomes by GC-MS and LC-HR-MS/MS techniques and of its detectability by GC-MS or LC-MS(n) standard screening approaches.
TLDR
An intake of 4-MEC should be detectable in urine by the GC-MS and LC-MS(n) standard urine screening approaches at least after overdose, and pathways proposed were similar to those described for the N-methyl homologue mephedrone and other related drugs. Expand
Dimethocaine, a synthetic cocaine analogue: studies on its in-vivo metabolism and its detectability in urine by means of a rat model and liquid chromatography–linear ion-trap (high-resolution) mass spectrometry
TLDR
DMC and its metabolites could be detected in the urine samples by use of GC–MS and LC–MSn standard urine-screening approaches (SUSAs), and these metabolites were used for identification of DMC in rat urine after application of a common user’s dose. Expand
Qualitative metabolism assessment and toxicological detection of xylazine, a veterinary tranquilizer and drug of abuse, in rat and human urine using GC–MS, LC–MSn, and LC–HR-MSn
TLDR
It should be possible to monitor application of xylazine assuming similar toxicokinetics in humans, and mainly the hydroxy metabolites were detected using the authors’ standard urine screening approaches by GC–MS and LC–MSn. Expand
New Psychoactive Substances 3-Methoxyphencyclidine (3-MeO-PCP) and 3-Methoxyrolicyclidine (3-MeO-PCPy): Metabolic Fate Elucidated with Rat Urine and Human Liver Preparations and their Detectability in Urine by GC-MS, “LC-(High Resolution)-MSn” and “LC-(High Resolution)-MS/MS”
TLDR
The detectability studies showed that the authors’ SUSAs were suitable for monitoring the intake of both drugs using the identified metabolites. Expand
GC-MS and LC-(high-resolution)-MSn studies on the metabolic fate and detectability of camfetamine in rat urine
TLDR
The metabolic fate and the detectability of CFA in urine was studied and to elucidate which cytochrome-P450 (CYP) isoenzymes are involved in the main metabolic steps, with the hydroxy-aryl CFA and the corresponding glucuronide being the most abundant. Expand
Diphenidine, a new psychoactive substance: metabolic fate elucidated with rat urine and human liver preparations and detectability in urine using GC-MS, LC-MSn , and LC-HR-MSn.
TLDR
After application of a common users' dose, diphenidine metabolites could be detected in rat urine by the authors' GC-MS as well as LC-MSn SUSA. Expand
Studies on the metabolism and the detectability of 4-methyl-amphetamine and its isomers 2-methyl-amphetamine and 3-methyl-amphetamine in rat urine using GC-MS and LC-(high-resolution)-MSn
TLDR
The aims of the presented work were to study the metabolism and detectability of each isomer in urine samples of 4-MA and its isomers and to confirm the intake of a commonly used dose of the MAs with an additional workup in rat urine. Expand
...
1
2
3
4
5
...

References

SHOWING 1-10 OF 17 REFERENCES
New cathinone-derived designer drugs 3-bromomethcathinone and 3-fluoromethcathinone: studies on their metabolism in rat urine and human liver microsomes using GC-MS and LC-high-resolution MS and their detectability in urine.
TLDR
For both compounds, detection in rat urine was possible within the authors' systematic toxicological analysis using both GC-MS and LC-MS(n) after a suspected recreational users dose. Expand
Qualitative studies on the metabolism and the toxicological detection of the fentanyl-derived designer drugs 3-methylfentanyl and isofentanyl in rats using liquid chromatography–linear ion trap–mass spectrometry (LC-MSn)
TLDR
In urine of rats after the administration of suspected recreational doses, the parent drugs could not be detected, but their common nor metabolite should therefore be the target for urine screening. Expand
Metabolism and toxicological detection of the designer drug 4-chloro-2,5-dimethoxyamphetamine in rat urine using gas chromatography-mass spectrometry
TLDR
The authors’ systematic toxicological analysis procedure using full-scan gas chromatography-mass spectrometry after acid hydrolysis, liquid-liquid extraction and microwave-assisted acetylation allowed the detection of an intake of a dose of DOC in rat urine that corresponds to a common drug user’s dose. Expand
Drugs of abuse screening in urine as part of a metabolite-based LC-MSn screening concept
TLDR
The presented LC-MSn method complements the well-established gas chromatography-mass spectroscopy procedure in the authors’ laboratory and could be used for drug screening in clinical and forensic toxicology and in doping control. Expand
Species differences in the metabolism of suprofen in laboratory animals and man.
TLDR
The metabolism of the oral anti-inflammatory agent suprofen (S), 2-4-(2-thienylcarbonyl)phenyl)propionic acid, has been studied in mice, rats, guinea pigs, dogs, monkeys, and human volunteers and its major metabolites were determined by GC/MS and HPLC techniques. Expand
The syntheses of 1-(2-thienyl)-2-(methylamino) propane (methiopropamine) and its 3-thienyl isomer for use as reference standards.
TLDR
The synthetic methodology presented here could be readily extended to the syntheses of analogous compounds and has been found to be separable from methiopropamine by gas chromatography using one of the routine protocols. Expand
Metabolic hydroxylation of the thiophene ring: isolation of 5-hydroxy-tienilic acid as the major urinary metabolite of tienilic acid in man and rat.
TLDR
A new very simple assay using HPLC and direct injection of urine led to a very precise and reproductible determination of tienilic acid and its hydroxylated metabolite in urine, the first example of metabolic hydroxYLation of the thiophene ring. Expand
Development of the first metabolite-based LC-MSn urine drug screening procedure-exemplified for antidepressants
TLDR
The presentedLC-MSn method complements established GC-MS or LC-MS procedures in the authors’ lab and allowed detecting unknown compounds based on known fragment structures and confirms the body passage. Expand
Mass spectral and GC data of drugs, poisons, pesticides, pollutants and their metabolites: Part 3 mass spectra (m/z222 to 777 amu).
Volume 1 (Methods, Tables). Methods. 1 Introduction. 2 Experimental Section. 2.1 Origin and choice of samples. 2.2 Sample preparation. 2.2.1 Standard extraction procedures. 2.2.1.1 StandardExpand
Disposition and metabolism of tenidap in the rat.
TLDR
After the oral administration of C-14 labeled tenidap, bile, urine and plasma were examined and an unusual reduction of hydroxytenidap took place, resulting in the formation of a novel thiolactone analog, suggesting the involvement of gut microflora. Expand
...
1
2
...