Literature DB >> 26648097

In vitro, in vivo and in silico metabolic profiling of α-pyrrolidinopentiothiophenone, a novel thiophene stimulant.

Madeleine J Swortwood1, Jeremy Carlier1, Kayla N Ellefsen1,2, Ariane Wohlfarth1,3, Xingxing Diao1, Marta Concheiro-Guisan1,4, Robert Kronstrand5,6, Marilyn A Huestis1.   

Abstract

BACKGROUND: Little or no pharmacological or toxicological data are available for novel psychoactive substances when they first emerge, making their identification and interpretation in biological matrices challenging. MATERIALS &
METHODS: A new synthetic cathinone, α-pyrrolidinopentiothiophenone (α-PVT), was incubated with hepatocytes and samples were analyzed using liquid chromatography coupled to a Q Exactive™ Orbitrap mass spectrometer. Authentic urine specimens from suspected α-PVT cases were also analyzed. Scans were data mined with Compound Discoverer™ for identification and structural elucidation of metabolites. RESULTS/
CONCLUSION: Seven α-PVT metabolites were identified in hepatocyte incubations, and in the authentic urine samples, also with an additional monohydroxylated product and a glucuronide of low intensity. α-PVT dihydroxypyrrolidinyl, α-PVT 2-ketopyrrolidinyl, α-PVT hydroxythiophenyl and α-PVT thiophenol had the most intense in vivo signals.

Entities:  

Keywords:  hepatocytes; high-resolution MS; metabolism; novel psychoactive substances; synthetic cathinone; α-PVT

Mesh:

Substances:

Year:  2015        PMID: 26648097      PMCID: PMC5493968          DOI: 10.4155/bio.15.237

Source DB:  PubMed          Journal:  Bioanalysis        ISSN: 1757-6180            Impact factor:   2.681


  38 in total

Review 1.  Metabolism of designer drugs of abuse: an updated review.

Authors:  Markus R Meyer; Hans H Maurer
Journal:  Curr Drug Metab       Date:  2010-06-01       Impact factor: 3.731

2.  Schedules of controlled substances: temporary placement of 10 synthetic cathinones into Schedule I. Final order.

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Journal:  Fed Regist       Date:  2014-03-07

3.  Metabolism of JWH-015, JWH-098, JWH-251, and JWH-307 in silico and in vitro: a pilot study for the detection of unknown synthetic cannabinoids metabolites.

Authors:  Sabina Strano-Rossi; Luca Anzillotti; Stefania Dragoni; Roberto Maria Pellegrino; Laura Goracci; Vincenzo Lorenzo Pascali; Gabriele Cruciani
Journal:  Anal Bioanal Chem       Date:  2014-05-08       Impact factor: 4.142

Review 4.  Clinical pharmacokinetics.

Authors:  A J Atkinson; W Kushner
Journal:  Annu Rev Pharmacol Toxicol       Date:  1979       Impact factor: 13.820

5.  UPLC/ESI-MS/MS-based determination of metabolism of several new illicit drugs, ADB-FUBINACA, AB-FUBINACA, AB-PINACA, QUPIC, 5F-QUPIC and α-PVT, by human liver microsome.

Authors:  Takahiro Takayama; Mayu Suzuki; Kenichiro Todoroki; Koichi Inoue; Jun Zhe Min; Ruri Kikura-Hanajiri; Yukihiro Goda; Toshimasa Toyo'oka
Journal:  Biomed Chromatogr       Date:  2014-06       Impact factor: 1.902

6.  The use of human hepatocytes to select compounds based on their expected hepatic extraction ratios in humans.

Authors:  T Lavé; S Dupin; C Schmitt; B Valles; G Ubeaud; R C Chou; D Jaeck; P Coassolo
Journal:  Pharm Res       Date:  1997-02       Impact factor: 4.200

7.  Studies on the metabolism and toxicological detection of the new designer drug 4'-methyl-alpha-pyrrolidinopropiophenone in urine using gas chromatography-mass spectrometry.

Authors:  Dietmar Springer; Frank T Peters; Giselher Fritschi; Hans H Maurer
Journal:  J Chromatogr B Analyt Technol Biomed Life Sci       Date:  2002-06-15       Impact factor: 3.205

8.  Identification of cytochrome p450 enzymes involved in the metabolism of 4'-methyl-alpha-pyrrolidinopropiophenone, a novel scheduled designer drug, in human liver microsomes.

Authors:  Dietmar Springer; Liane D Paul; Roland F Staack; Thomas Kraemer; Hans H Maurer
Journal:  Drug Metab Dispos       Date:  2003-08       Impact factor: 3.922

9.  Simultaneous quantification of 28 synthetic cathinones and metabolites in urine by liquid chromatography-high resolution mass spectrometry.

Authors:  Marta Concheiro; Sebastien Anizan; Kayla Ellefsen; Marilyn A Huestis
Journal:  Anal Bioanal Chem       Date:  2013-10-03       Impact factor: 4.142

10.  Synthetic cathinone abuse.

Authors:  Michael Capriola
Journal:  Clin Pharmacol       Date:  2013-07-02
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  10 in total

1.  Behavioral evidence for the abuse potential of the novel synthetic cathinone alpha-pyrrolidinopentiothiophenone (PVT) in rodents.

Authors:  Jae Hoon Cheong; Mee Jung Choi; Choon-Gon Jang; Yong Sup Lee; Sooyeun Lee; Hee Jin Kim; Joung-Wook Seo; Seong Shoon Yoon
Journal:  Psychopharmacology (Berl)       Date:  2017-01-09       Impact factor: 4.530

2.  Identification of New Synthetic Cannabinoid ADB-CHMINACA (MAB-CHMINACA) Metabolites in Human Hepatocytes.

Authors:  Jeremy Carlier; Xingxing Diao; Cristina Sempio; Marilyn A Huestis
Journal:  AAPS J       Date:  2017-01-09       Impact factor: 4.009

3.  In vitro and in vivo human metabolism of a new synthetic cannabinoid NM-2201 (CBL-2201).

Authors:  Xingxing Diao; Jeremy Carlier; Mingshe Zhu; Shaokun Pang; Robert Kronstrand; Karl B Scheidweiler; Marilyn A Huestis
Journal:  Forensic Toxicol       Date:  2016-07-06       Impact factor: 4.096

4.  In silico, in vitro, and in vivo human metabolism of acetazolamide, a carbonic anhydrase inhibitor and common "diuretic and masking agent" in doping.

Authors:  Francesco P Busardò; Alfredo F Lo Faro; Ascanio Sirignano; Raffaele Giorgetti; Jeremy Carlier
Journal:  Arch Toxicol       Date:  2022-04-11       Impact factor: 6.168

5.  In Vitro and In Vivo Human Metabolism of Synthetic Cannabinoids FDU-PB-22 and FUB-PB-22.

Authors:  Xingxing Diao; Karl B Scheidweiler; Ariane Wohlfarth; Shaokun Pang; Robert Kronstrand; Marilyn A Huestis
Journal:  AAPS J       Date:  2016-01-25       Impact factor: 4.009

6.  Untargeted metabolomics by high resolution mass spectrometry coupled to normal and reversed phase liquid chromatography as a tool to study the in vitro biotransformation of new psychoactive substances.

Authors:  Sascha K Manier; Andreas Keller; Jan Schäper; Markus R Meyer
Journal:  Sci Rep       Date:  2019-02-26       Impact factor: 4.379

7.  Metabolism study and toxicological determination of mephtetramine in biological samples by liquid chromatography coupled with high-resolution mass spectrometry.

Authors:  Sara Odoardi; Serena Mestria; Giulia Biosa; Raffaella Arfè; Micaela Tirri; Matteo Marti; Sabina Strano Rossi
Journal:  Drug Test Anal       Date:  2021-05-04       Impact factor: 3.234

8.  Human Hepatocyte 4-Acetoxy-N,N-Diisopropyltryptamine Metabolite Profiling by Reversed-Phase Liquid Chromatography Coupled with High-Resolution Tandem Mass Spectrometry.

Authors:  Sara Malaca; Marilyn A Huestis; Leonardo Lattanzio; Luigi T Marsella; Adriano Tagliabracci; Jeremy Carlier; Francesco P Busardò
Journal:  Metabolites       Date:  2022-07-29

9.  Strategies to distinguish new synthetic cannabinoid FUBIMINA (BIM-2201) intake from its isomer THJ-2201: metabolism of FUBIMINA in human hepatocytes.

Authors:  Xingxing Diao; Karl B Scheidweiler; Ariane Wohlfarth; Mingshe Zhu; Shaokun Pang; Marilyn A Huestis
Journal:  Forensic Toxicol       Date:  2016-03-28       Impact factor: 4.096

Review 10.  Psychoactive Drugs-From Chemical Structure to Oxidative Stress Related to Dopaminergic Neurotransmission. A Review.

Authors:  George Jîtcă; Bianca E Ősz; Amelia Tero-Vescan; Camil E Vari
Journal:  Antioxidants (Basel)       Date:  2021-03-04
  10 in total

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