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Simon D. Brandt

Liverpool John Moores University, Özyeğin University

93 papers in the library · 2,731 citations · publishing 2004-2026

Papers

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Pharmacological characterizations of the 'legal high' fluorolintane and isomers.

European Journal of Pharmacology August 15, 2019 Jason Wallach, Tristan Colestock, Julià Agramunt et al.

1,2-Diarylethylamines represent a class of molecules that have shown potential in the treatment of pain, epilepsy, neurodegenerative disease and depression. Examples include lefetamine, remacemide, and lanicemine. Recently, several 1,2-diarylethylamines including the dissociatives diphenidine, methoxphenidine and ephenidine as well as the opioid MT-45, have appeared as 'research chemicals' or...

In vitro metabolic fate of nine LSD-based new psychoactive substances and their analytical detectability in different urinary screening procedures

Analytical and Bioanalytical Chemistry July 19, 2019 Lea Wagmann, Lilian H. J. Richter, Tobias Kehl et al.

The market of new psychoactive substances (NPS) is characterized by a high turnover and thus provides several challenges for analytical toxicology. The analysis of urine samples often requires detailed knowledge about metabolism given that parent compounds either may be present only in small amounts or may not even be excreted. Hence, knowledge of the metabolism of NPS is a prerequisite for the...

Validation of an LC-MS/MS method for the quantitative analysis of 1P-LSD and its tentative metabolite LSD in fortified urine and serum samples including stability tests for 1P-LSD under different storage conditions

Journal of Pharmaceutical and Biomedical Analysis May 28, 2019 Christina Grumann, Kerstin Henkel, Alexander Stratford et al. 27 citations

A variety of hallucinogens of the lysergamide type has emerged on the drug market in recent years and one such uncontrolled derivative of lysergic acid diethylamide (LSD) is 1-propionyl-LSD (1P-LSD). Due to the high potency of LSD and some of its derivatives (common doses: 50-200 μg), sensitive methods are required for the analysis of biological samples such as serum and urine. The occurrence...

Return of the lysergamides. Part V: Analytical and behavioural characterization of 1‐butanoyl‐d‐lysergic acid diethylamide (1B‐LSD)

Drug Testing and Analysis May 13, 2019 Simon D. Brandt, Pierce V. Kavanagh, Folker Westphal et al. 72 citations

Abstract The psychedelic properties of lysergic acid diethylamide (LSD) have captured the imagination of researchers for many years and its rediscovery as an important research tool is evidenced by its clinical use within neuroscientific and therapeutic settings. At the same time, a number of novel LSD analogs have recently emerged as recreational drugs, which makes it necessary to study their...

Syntheses and analytical characterizations of the research chemical 1‐[1‐(2‐fluorophenyl)‐2‐phenylethyl]pyrrolidine (fluorolintane) and five of its isomers

Drug Testing and Analysis April 30, 2019 Michael Dybek, Jason Wallach, Pierce V. Kavanagh et al. 9 citations

Abstract A number of substances based on the 1,2‐diarylethylamine template have been investigated for various potential clinical applications whereas others have been encountered as research chemicals sold for non‐medical use. Some of these substances have transpired to function as NMDA receptor antagonists that elicit dissociative effects in people who use these substances recreationally....

2-Aminoindan and its Ring-Substituted Derivatives Interact with Plasma Membrane Monoamine Transporters and α2-Adrenergic Receptors

Psychopharmacology March 1, 2019 Adam L. Halberstadt, Simon D. Brandt, Donna Walther et al.

Over the last decade, many new psychostimulant analogues have appeared on the recreational drug market and most are derivatives of amphetamine or cathinone. Another class of designer drugs is derived from the 2-aminoindan structural template. Several members of this class, including the parent compound 2-aminoindan (2-AI), have been sold as designer drugs. Another aminoindan derivative,...

Comparison of the behavioral effects of mescaline analogs using the head twitch response in mice

Journal of Psychopharmacology February 21, 2019 Adam L. Halberstadt, Muhammad Chatha, Stephen J. Chapman et al. 25 citations

Background: In recent years, there has been increasing scientific interest in the effects and pharmacology of serotonergic hallucinogens. While a large amount of experimental work has been conducted to characterize the behavioral response to hallucinogens in rodents, there has been little systematic investigation of mescaline and its analogs. The hallucinogenic potency of mescaline is increased...

Pharmacological characterization of the LSD analog N-ethyl-N-cyclopropyl lysergamide (ECPLA)

Psychopharmacology February 14, 2019 Adam L. Halberstadt, Landon M. Klein, Muhammad Chatha et al. 25 citations

Rationale The lysergamide lysergic acid diethylamide (LSD) is a prototypical classical hallucinogen with remarkably high potency. LSD remains a popular recreational drug but is also becoming an important research tool for medical and neuroscience studies. Recently, several lysergamides that are close structural analogs of LSD have been sold as recreational drugs, which suggests that further...

Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases.

Drug Testing and Analysis February 1, 2019 Lea Wagmann, Simon D. Brandt, Alexander Stratford et al. 26 citations

Psychoactive substances of the 2C-series (2Cs) are phenethylamine-derived designer drugs that can induce psychostimulant and hallucinogenic effects. Chemically, the classic 2Cs contain two methoxy groups in positions 2 and 5 of the phenyl ring, whereas substances of the so-called FLY series contain rigidified methoxy groups integrated in a 2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran core. One...

Comparison of the behavioral responses induced by phenylalkylamine hallucinogens and their tetrahydrobenzodifuran ("FLY") and benzodifuran ("DragonFLY") analogs.

Neuropharmacology 2019 Adam L. Halberstadt, Muhammad Chatha, Alexander Stratford et al. 25 citations

In recent years, rigid analogs of phenylalkylamine hallucinogens have appeared as recreational drugs. Examples include 2-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)ethan-1-amine (2C-B-FLY) and 1-(8-bromobenzo[1,2-b;4,5-b']difuran-4-yl)-2-aminopropane (Bromo-DragonFLY, DOB-DFLY). Although some rigid compounds such as DOB-DFLY reportedly have higher potency than their non-rigid...

Receptor binding profiles and behavioral pharmacology of ring-substituted N,N-diallyltryptamine analogs.

Neuropharmacology November 1, 2018 Landon M. Klein, Nicholas V. Cozzi, Paul F. Daley et al. 43 citations

Substantial effort has been devoted toward understanding the psychopharmacological effects of tryptamine hallucinogens, which are thought to be mediated by activation of 5-HT2A and 5-HT1A receptors. Recently, several psychoactive tryptamines based on the N,N-diallyltryptamine (DALT) scaffold have been encountered as recreational drugs. Despite the apparent widespread use of DALT derivatives in...

DARK Classics in Chemical Neuroscience: Aminorex Analogues

ACS Chemical Neuroscience September 30, 2018 Julian Maier, Felix P. Mayer, Simon D. Brandt et al. 15 citations

Aminorex (5-phenyl-4,5-dihydro-1,3-oxazol-2-amine) and 4-methylaminorex (4-methyl-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine) are psychostimulants that have long been listed in Schedules IV and I of the UN Convention on Psychotropic Substances of 1971. However, a range of psychoactive analogues exist that are not internationally controlled and therefore often classified as new psychoactive...

The psychostimulant (±)-cis-4,4′-dimethylaminorex (4,4′-DMAR) interacts with human plasmalemmal and vesicular monoamine transporters

Neuropharmacology June 23, 2018 Julian Maier, Felix P. Mayer, Dino Luethi et al. 24 citations

(±)-cis-4,4′-Dimethylaminorex (4,4′-DMAR) is a new psychoactive substance (NPS) that has been associated with 31 fatalities and other adverse events in Europe between June 2013 and February 2014. We used in vitro uptake inhibition and transporter release assays to determine the effects of 4,4′-DMAR on human high-affinity transporters for dopamine (DAT), norepinephrine (NET) and serotonin...

Synthesis, analytical characterization, and monoamine transporter activity of the new psychoactive substance 4‐methylphenmetrazine (4‐MPM), with differentiation from its ortho‐ and meta‐ positional isomers

Drug Testing and Analysis April 19, 2018 Gavin McLaughlin, Michael H. Baumann, Pierce V. Kavanagh et al. 8 citations

The availability of new psychoactive substances (NPS) on the recreational drug market continues to create challenges for scientists in the forensic, clinical and toxicology fields. Phenmetrazine (3-methyl-2-phenylmorpholine) and an array of its analogs form a class of psychostimulants that are well documented in the patent and scientific literature. The present study reports on two...

Syntheses, analytical and pharmacological characterizations of the 'legal high' 4-[1-(3-methoxyphenyl)cyclohexyl]morpholine (3-MeO-PCMo) and analogues.

Drug Testing and Analysis February 1, 2018 Tristan Colestock, Jason Wallach, Matt Mansi et al. 14 citations

New psychoactive substances (NPS) are commonly referred to as 'research chemicals', 'designer drugs' or 'legal highs'. One NPS class is represented by dissociative anesthetics, which include analogues of the arylcyclohexylamine phencyclidine (PCP), ketamine and diphenidine. A recent addition to the NPS market was 4-[1-(3-methoxyphenyl)cyclohexyl]morpholine (3-MeO-PCMo), a morpholine analogue of...

Metabolism of the tryptamine-derived new psychoactive substances 5-MeO-2-Me-DALT, 5-MeO-2-Me-ALCHT, and 5-MeO-2-Me-DIPT and their detectability in urine studied by GC-MS, LC-MSn , and LC-HR-MS/MS.

Drug Testing and Analysis 2018 Achim T. Caspar, Jonas B Gaab, Julian A Michely et al. 33 citations

Many N,N-dialkylated tryptamines show psychoactive properties and were encountered as new psychoactive substances. The aims of the presented work were to study the phase I and II metabolism and the detectability in standard urine screening approaches (SUSA) of 5-methoxy-2-methyl-N,N-diallyltryptamine (5-MeO-2-Me-DALT), 5-methoxy-2-methyl-N-allyl-N-cyclohexyltryptamine (5-MeO-2-Me-ALCHT), and...

Identification of pyrolysis products of the new psychoactive substance 2-amino-1-(4-bromo-2,5-dimethoxyphenyl)ethanone hydrochloride (bk-2C-B) and its iodo analogue bk-2C-I.

Drug Testing and Analysis 2018 Kelly B Texter, Rachel Waymach, Pierce V. Kavanagh et al. 9 citations

2-Amino-1-(4-bromo-2,5-dimethoxyphenyl)ethanone hydrochloride (bk-2C-B) has recently emerged as a new psychoactive substance (NPS). It is most commonly consumed orally, although there are indications that it might also be ingested by inhalation or 'smoking'. Information about the stability of bk-2C-B when exposed to heat is unavailable and the potential for pyrolytic degradation and formation...

Phencyclidine-Based New Psychoactive Substances.

Handbook of experimental pharmacology 2018 Jason Wallach, Simon D. Brandt

The serendipitous discovery of phencyclidine (PCP) in 1956 sets the stage for significant research efforts that resulted in a plethora of analogs and derivatives designed to explore the biological effects of this class. PCP soon became the prototypical dissociative agent that eventually sneaked through the doors of clinical laboratories and became an established street drug. Estimations suggest...

1,2-Diarylethylamine- and Ketamine-Based New Psychoactive Substances.

Handbook of experimental pharmacology 2018 Jason Wallach, Simon D. Brandt

While phencyclidine (PCP) and ketamine remain the most well-studied and widely known dissociative drugs, a number of other agents have appeared since the late 1950s and early 1960s, when the pharmacological potential of this class was first realized. For example, hundreds of compounds have been pursued as part of legitimate research efforts to explore these agents. Some of these found their way...

Self-Experiments with Psychoactive Substances: A Historical Perspective.

Handbook of experimental pharmacology 2018 Torsten Passie, Simon D. Brandt

The purpose of this chapter is to highlight the rich tradition of self-experiments (SEs) with psychoactive substances carried out by scientists and therapists for more than a century. Scientifically inspired controlled SEs dominated until the end of the twentieth century, when ethical requirements minimized controlled SEs and "wild" SEs expanded particularly with the emergence of new...

Fluorinated phenmetrazine “legal highs” act as substrates for high-affinity monoamine transporters of the SLC6 family

Neuropharmacology October 12, 2017 Felix P. Mayer, Nadine V. Burchardt, Ann M Decker et al. 30 citations

A variety of new psychoactive substances (NPS) are appearing in recreational drug markets worldwide. NPS are compounds that target various receptors and transporters in the central nervous system to achieve their psychoactive effects. Chemical modifications of existing drugs can generate NPS that are not controlled by current legislation, thereby providing legal alternatives to controlled...

Impact of Novel Psychoactive Substances on Clinical and Forensic Toxicology and Global Public Health

Clinical Chemistry June 30, 2017 Marilyn A. Huestis, Simon D. Brandt, Suman Rana et al. 42 citations

Novel psychoactive substances (NPS) have been a part of the landscape of clinical and forensic toxicology for over a century, beginning with the introduction of a few new drugs like heroin, lysergic acid diethylamide (LSD), 3,4-methylenedioxymethamphetamine (MDMA) and gammahydroxybutyric acid (GHB). However, after the appearance of synthetic cannabinoids in the early 2000’s there was a rapid...

Return of the lysergamides. Part IV: Analytical and pharmacological characterization of lysergic acid morpholide (LSM‐775)

Drug Testing and Analysis June 5, 2017 Simon D. Brandt, Pierce V. Kavanagh, Brendan Twamley et al. 56 citations

Lysergic acid diethylamide (LSD) is perhaps one of the best‐known psychoactive substances and many structural modifications of this prototypical lysergamide have been investigated. Several lysergamides were recently encountered as ‘research chemicals’ or new psychoactive substances (NPS). Although lysergic acid morpholide (LSM‐775) appeared on the NPS market in 2013, there is disagreement in...

Online test purchased new psychoactive substances in 5 different European countries: A snapshot study of chemical composition and price.

The International journal on drug policy June 1, 2017 Tibor Markus Brunt, Amanda Marie Atkinson, Thomas Nefau et al.

New psychoactive substances (NPS) are on offer worldwide online, in order to shed light on the purity and price of these substances in the European Union, a research collaboration was set up involving France, United Kingdom (UK), the Netherlands, Czech Republic and Poland. Per country, around 10 different NPS were test purchased from different webshops. Then, chemical analysis of NPS was done...

Return of the lysergamides. Part III: Analytical characterization of N6-ethyl-6-norlysergic acid diethylamide (ETH-LAD) and 1-propionyl ETH-LAD (1P–ETH-LAD)

Drug Testing and Analysis May 10, 2017 Simon D. Brandt, Pierce V. Kavanagh, Folker Westphal et al. 44 citations

The psychoactive properties of lysergic acid diethylamide (LSD) have fascinated scientists across disciplines and the exploration of other analogues and derivatives has been motivated by deepening the understanding of ligand-receptor interactions at the molecular level as well as by the search for new therapeutics. Several LSD congeners have appeared on the new psychoactive substances (NPS)...