Synthetic Cannabinoids and Synthetic Cannabinoid-Induced Psychotic Disorders

2018 ◽  
pp. 199-220 ◽  
Author(s):  
Papanti Duccio ◽  
Schifano Fabrizio ◽  
Orsolini Laura
Keyword(s):  
Psychotic Disorders ◽  
Synthetic Cannabinoids ◽  
Synthetic Cannabinoid

scholarly journals Identification and Analytical Characterization of a Novel Synthetic Cannabinoid-Type Substance in Herbal Material in Europe

Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 793
Author(s):  
Emmanouil D. Tsochatzis ◽  
Joao Alberto Lopes ◽  
Margaret V. Holland ◽  
Fabiano Reniero ◽  
Giovanni Palmieri ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Cannabinoid Receptor ◽  
Analytical Data ◽  
Synthetic Cannabinoids ◽  
Synthetic Cannabinoid ◽  
Gas Chromatography Mass Spectrometry ◽  
New Psychoactive Substances ◽  
Synthetic Cannabinoid Receptor Agonists ◽  
Analytical Laboratories

The rapid diffusion of new psychoactive substances (NPS) presents unprecedented challenges to both customs authorities and analytical laboratories involved in their detection and characterization. In this study an analytical approach to the identification and structural elucidation of a novel synthetic cannabimimetic, quinolin-8-yl-3-[(4,4-difluoropiperidin-1-yl) sulfonyl]-4-methylbenzoate (2F-QMPSB), detected in seized herbal material, is detailed. An acid precursor 4-methyl-3-(4,4-difluoro-1-piperidinylsulfonyl) benzoic acid (2F-MPSBA), has also been identified in the same seized material. After extraction from the herbal material the synthetic cannabimimetic, also referred to as synthetic cannabinoid receptor agonists or “synthetic cannabinoids”, was characterized using gas chromatography-mass spectrometry (GC-MS), 1H, 13C, 19F and 15N nuclear magnetic resonance (NMR) and high-resolution tandem mass spectrometry (HR-MS/MS) combined with chromatographic separation. A cheminformatics platform was used to manage and interpret the analytical data from these techniques.

scholarly journals Activity-Based Detection of Cannabinoids in Serum and Plasma Samples

2018 ◽  
Vol 64 (6) ◽  
pp. 918-926 ◽  
Author(s):  
Annelies Cannaert ◽  
Jolien Storme ◽  
Cornelius Hess ◽  
Volker Auwärter ◽  
Sarah M R Wille ◽  
...  
Keyword(s):  
Cannabinoid Receptors ◽  
Cannabinoid Receptor ◽  
Synthetic Cannabinoids ◽  
Receptor Activation ◽  
Synthetic Cannabinoid ◽  
New Psychoactive Substances ◽  
Simple Liquid ◽  
Analytical Sensitivity ◽  
Monitoring Centre ◽  
Screening Strategies

Abstract BACKGROUND Synthetic cannabinoids are the largest group of new psychoactive substances monitored by the European Monitoring Centre of Drugs and Drug Addiction. The rapid proliferation of novel analogs makes the detection of these new derivatives challenging and has initiated considerable interest in the development of so-called “untargeted” screening strategies to detect these compounds. METHODS We developed new, stable bioassays in which cannabinoid receptor activation by cannabinoids led to recruitment of truncated β-arrestin 2 (βarr2) to the cannabinoid receptors, resulting in functional complementation of a split luciferase, allowing readout via bioluminescence. Aliquots (500 μL) of authentic serum (n = 45) and plasma (n = 73) samples were used for simple liquid–liquid extraction with hexane:ethyl acetate (99:1 v/v). Following evaporation and reconstitution in 100 μL of Opti-MEM® I/methanol (50/50 v/v), 10 μL of these extracts was analyzed in the bioassays. RESULTS Truncation of βarr2 significantly (for both cannabinoid receptors; P = 0.0034 and 0.0427) improved the analytical sensitivity over the previously published bioassays applied on urine samples. The new bioassays detected cannabinoid receptor activation by authentic serum or plasma extracts, in which synthetic cannabinoids were present at low- or sub-nanogram per milliliter concentration or in which Δ9-tetrahydrocannabinol was present at concentrations >12 ng/mL. For synthetic cannabinoid detection, analytical sensitivity was 82%, with an analytical specificity of 100%. CONCLUSIONS The bioassays have the potential to serve as a first-line screening tool for (synthetic) cannabinoid activity in serum or plasma and may complement conventional analytical assays and/or precede analytical (mass spectrometry based) confirmation.

Health Risk Behaviors With Synthetic Cannabinoids Versus Marijuana

2017 ◽  
pp. 5-14
Author(s):  
Heather B. Clayton ◽  
Richard Lowry ◽  
Carmen Ashley ◽  
Amy Wolkin ◽  
Althea M. Grant
Keyword(s):  
Substance Use ◽  
Risk Behaviors ◽  
Synthetic Cannabinoids ◽  
Health Risk Behaviors ◽  
Synthetic Cannabinoid ◽  
Self Report ◽  
Behavioral Risk ◽  
Substance Use Prevention ◽  
The Past ◽  
Nationally Representative

BACKGROUND AND OBJECTIVES Data are limited on the behavioral risk correlates of synthetic cannabinoid use. The purpose of this study was to compare the behavioral risk correlates of synthetic cannabinoid use with those among marijuana users. METHODS Data from the 2015 Youth Risk Behavior Survey, a cross-sectional survey conducted in a nationally representative sample of students in grades 9 through 12 (N = 15 624), were used to examine the association between self-reported type of marijuana use (ie, never use of marijuana and synthetic cannabinoids, ever use of marijuana only, and ever use of synthetic cannabinoids) and self-report of 36 risk behaviors across 4 domains: substance use, injury/violence, mental health, and sexual health. Multivariable models were used to calculate adjusted prevalence ratios. RESULTS Students who ever used synthetic cannabinoids had a significantly greater likelihood of engaging in each of the behaviors in the substance use and sexual risk domains compared with students who ever used marijuana only. Students who ever used synthetic cannabinoids were more likely than students who ever used marijuana only to have used marijuana before age 13 years, to have used marijuana ≥1 times during the past 30 days, and to have used marijuana ≥20 times during the past 30 days. Several injury/violence behaviors were more prevalent among students who ever used synthetic cannabinoids compared with students who ever used marijuana only. CONCLUSIONS Health professionals and school-based substance use prevention programs should include strategies focused on the prevention of both synthetic cannabinoids and marijuana.

scholarly journals Hospital Stay in Synthetic Cannabinoid Users With Bipolar Disorder, Schizophrenia, or Other Psychotic Disorders Compared With Cannabis Users

2019 ◽  
Vol 80 (2) ◽  
pp. 230-235 ◽  
Author(s):  
Huiqiong Deng ◽  
Pratikkumar V. Desai ◽  
Satyajit Mohite ◽  
Olaoluwa O. Okusaga ◽  
Xiang Yang Zhang ◽  
...  
Keyword(s):  
Bipolar Disorder ◽  
Hospital Stay ◽  
Psychotic Disorders ◽  
Synthetic Cannabinoid

scholarly journals T195. PSYCHOTIC DISORDERS IN PATIENTS WHO USE SYNTHETIC CANNABINOIDS: CLINICAL CHARACTERISTICS AND PATIENT PROFILE

2020 ◽  
Vol 46 (Supplement_1) ◽  
pp. S305-S306
Author(s):  
Valentin Skriabin ◽  
Maria Vinnikova
Keyword(s):  
Clinical Characteristics ◽  
Psychotic Disorders ◽  
Clinical Presentation ◽  
Violent Behavior ◽  
Synthetic Cannabinoids ◽  
Psychotic Episode ◽  
Patient Profile ◽  
Observational Cohort ◽  
Male Patients

Abstract Background Cannabidiol (CBD) and delta-9-tetrahydrocannabinol (THC) are the two principal ingredients of natural cannabis with counteracting functions. Synthetic cannabinoids (SCs) are much more potent than natural cannabis, since they act as a more potent full agonist at the cannabinoid subtype 1 receptor than THC, and they also lack cannabinoids such as CBD that may otherwise counteract psychoactive properties of THC. Therefore, SCs may induce a more severe clinical presentation than natural cannabis does: the use of SCs may be associated with agitation, anxiety, tachycardia, hallucinations, irritability, memory and cognitive impairment, violent behavior, unresponsiveness, and psychosis. Clinical characteristics, specificity of the disease course and patient profile of the SC-induced psychoses are still poorly characterized in the scientific literature. The present study was therefore designed to evaluate the psychotic disorders in patients with synthetic cannabinoid use disorder in terms of patient profile and clinical characteristics with reference to their follow-up. Methods A total of 60 male patients (n=60; mean (standard deviation [SD]) age: 23.6 (3.5) years) diagnosed with psychotic disorder induced by the SC use who were hospitalized at the intensive care unit or emergency department of the Moscow Research and Practical Centre on Addictions of the Moscow Department of Healthcare were included in this single-centre, longitudinal, observational cohort study. The catamnestic follow-up period was up to 2 years. Results We evaluated different clinical cases of SC-induced psychoses and identified four clinical types of them on the ground of leading psychopathological syndrome during the patient’s entire length of hospitalization: Then we performed a catamnestic follow-up of patients to reveal the possible schizophrenic process manifestation in patients who use SC. Catamnestic follow-up revealed that manifestation of the schizophrenic process was present in 8 patients (13% of cases). Discussion Our results revealed that SC-induced psychoses affect young adults primarily. Consistent with the statement that the majority of first-time SC users are experienced marijuana smokers, SC was used following other transitional substances rather than as the first substance in the majority of our patients, with cannabis being the most popular antecedent substance. SC was not the first substance used in the majority of our patients, and it had been preceded by use of other transitional substances, such as cannabis in most cases. Despite the exogenous nature, structurally such psychoses are often endoformic. For instance, even the delirium is atypical and includes the elements of Kandinsky-Clerambault’s syndrome. Psychopathologically hallucinations and delusions dominate in the clinical presentation of the psychoses (with predominant hallucinatory symptoms or affective paranoid symptoms). Development of substance-induced psychoses is often associated with the manifestation of the schizophrenic process (in our study it was revealed in 13% of cases). It is extremely difficult to create a differential diagnosis between such psychotic disorders and a primary endogenous psychotic episode. In such cases the appearance of deficit symptoms specific for schizophrenia becomes crucial.

Synthesis of the 5-Fluoro-4-hydroxypentyl Side Chain Metabolites of Synthetic Cannabinoids 5F-APINACA and CUMYL-5F-PINACA

Synthesis ◽  
2018 ◽  
Vol 50 (23) ◽  
pp. 4683-4689 ◽  
Author(s):  
Mark Trudell ◽  
Ryan McKinnie ◽  
Tasneam Darweesh ◽  
Phoebe Zito ◽  
Terrell Shields
Keyword(s):  
Efficient Method ◽  
Synthetic Cannabinoids ◽  
Synthetic Cannabinoid ◽  
Protecting Groups ◽  
Side Chain ◽  
Hydroxy Metabolites

An efficient method for the construction of the 5-fluoro-4-hydroxypentyl side chain common to a number of synthetic cannabinoid metabolites was developed. A series of hydroxyl protecting groups was examined to assess the viability as orthogonal protecting groups for epoxidation and regioselective hydrofluorination. The 1-[5-fluoro-4-(diphenyl-tert-butylsilyloxy)]pentyl tosylate was prepared in 67% overall yield (six steps) from pent-4-en-1-ol and was employed for the synthesis of the 4-hydroxy metabolites of the synthetic cannabinoid 5F-APINACA and CUMYL-5F-PINACA.

Emerging Synthetic Cannabinoids: Development and Validation of a Novel Liquid Chromatography Quadrupole Time-of-Flight Mass Spectrometry Assay for Real-Time Detection

2019 ◽  
Vol 44 (3) ◽  
pp. 207-217 ◽  
Author(s):  
Alex J Krotulski ◽  
Amanda L A Mohr ◽  
Barry K Logan
Keyword(s):  
United States ◽  
Mass Spectrometry ◽  
Liquid Chromatography ◽  
Real Time ◽  
Synthetic Cannabinoids ◽  
Time Of Flight ◽  
Forensic Toxicology ◽  
The United States ◽  
Synthetic Cannabinoid ◽  
Flight Mass Spectrometry

Abstract Synthetic cannabinoids pose significant threats to public health and safety, as their implications in overdose and adverse events continue to arise in United States and around the world. Synthetic cannabinoids have seen several generations of chemically diverse structural elements, impacting potency and effects. These factors create new analytical challenges for forensic laboratories. This report describes an efficient liquid chromatography/quadrupole time-of-flight mass spectrometry (LC-QTOF-MS) assay for the identification of synthetic cannabinoid parent compounds and metabolites, including real-time identification of emergent compounds, using a SCIEX TripleTOF® 5600+ with non-targeted SWATH® acquisition. Method validation evaluated precision/accuracy, limits of detection, interferences, processed sample stability and carryover, for which 19 parent compounds and 19 metabolites were tested. To demonstrate feasibility, de-identified blood sample extracts were acquired from a large forensic toxicology laboratory and analyzed using the validated LC-QTOF-MS assay. In mid-2018, 200 blood extracts were analyzed, demonstrating a 19% positivity rate with > 94% agreement rate with original testing. In addition, three newly discovered synthetic cannabinoids were identified, including 5F-MDMB-PICA, 4-cyano CUMYL-BUTINACA and 5F-EDMB-PINACA. These synthetic cannabinoids were previously unreported in forensic toxicology casework in the United States. 5F-MDMB-PICA has become the most prevalent synthetic cannabinoid in United States, as of early 2019. These results demonstrate the effectiveness of this assay and workflow in the identification and characterization of synthetic cannabinoids, as well as the usefulness of sample-mining using non-targeted mass acquisition by LC-QTOF-MS for the discovery of NPS. High resolution mass spectrometry should be considered when developing new or novel assays for synthetic cannabinoids.

scholarly journals The synthetic cannabinoid JWH-018 modulates Saccharomyces cerevisiae energetic metabolism

2019 ◽  
Vol 19 (5) ◽  
Author(s):  
Carla Ferreira ◽  
Joana Couceiro ◽  
Carlos Família ◽  
Carolina Jardim ◽  
Pedro Antas ◽  
...  
Keyword(s):  
Saccharomyces Cerevisiae ◽  
Molecular Mechanisms ◽  
Synthetic Cannabinoids ◽  
Cellular Level ◽  
Pentose Phosphate ◽  
Synthetic Cannabinoid ◽  
Glycolytic Flux ◽  
Vast Number ◽  
2D Gel ◽  
The Impact

ABSTRACT Synthetic cannabinoids are a group of novel psychoactive substances with similar properties to Δ9-THC. Among the vast number of synthetic cannabinoids, designed to be tested in clinical trials, JWH-018 was the first novel psychoactive substance found in the recreational drug marketplace. The consumption of JWH-018 shows typical effects of CB1 agonists including sedation, cognitive dysfunction, tachycardia, postural hypotension, dry mouth, ataxia and psychotropic effects, but appeared to be more potent than Δ9-THC. However, studies on human cells have shown that JWH-018 toxicity depends on the cellular line used. Despite these studies, the underlying molecular mechanisms to JWH-018 action has not been clarified yet. To understand the impact of JWH-018 at molecular and cellular level, we used Saccharomyces cerevisiae as a model. The results showed an increase in yeast growth rate in the presence of this synthetic cannabinoid due to an enhancement in the glycolytic flux at expense of a decrease in pentose phosphate pathway, judging by 2D-Gel proteomic analysis, qRT-PCR experiments and ATP measurements. Overall, our results provide insights into molecular mechanisms of JWH-018 action, also indicating that Saccharomyces cerevisiae is a good model to study synthetic cannabinoids.

Clinical Variants of Psychopathological Disorders in Users of Synthetic Cannabinoids (Spices)

2017 ◽  
Vol 41 (S1) ◽  
pp. S199-S200
Author(s):  
N. Bokhan ◽  
G.Y. Selivanov
Keyword(s):  
Psychotic Disorders ◽  
Late Onset ◽  
Paranoid Schizophrenia ◽  
Synthetic Cannabinoids ◽  
Designer Drug ◽  
Addiction Psychiatry ◽  
Continuous Type ◽  
Icd 10 ◽  
Group 5 ◽  
Group 2

IntroductionThe problem of mental health of synthetic (“designer”) drug or “spice” users draws the increasing attention of experts of various areas in psychiatry, addiction psychiatry and psychotherapy.Research objective To classify and describe the psychotic states arising after the use of “spice”; to define the personality changes and probable consequences of the use observed in patients in the conditions of a hospital.Material and methodsOne hundred and one patients (93 men and 8 women; mean age 27.8 ± 7.6 years) with dependence on “spice” revealed between 2014 and 2015 were examined. History taking, clinical-psychopathological investigation and experimental psychological testing were used.Results and discussionAs a result of research the patients were divided into 5 groups according to criteria of ICD-10:– group 1: acute intoxication with delirium (n = 16; 15.84%);– group 2: residual and late-onset psychotic disorders like flashbacks (n = 9; 8.92%);– group 3: withdrawal state with delirium (n = 32; 31.68%);– group 4: psychotic disorder, mainly hallucinatory (n = 30; 29.70%);– group 5: paranoid schizophrenia (n = 14; 13.86%).The use of synthetic cannabinoids (“spice”) can initiate transient psychotic episodes, serve as the contributing factor of development of paranoid schizophrenia, continuous type of the course, leads to “accentuation” of schizoid, paranoid and psychopathic traits of the personality. It is proposed to make up a question of the possibility of additional use of the clarifying designation “synthetic cannabinoids/spice” at reference of patients using synthetic cannabinoids to the section of ICD-10 F12 “Mental and behavioural disorders due to use of cannabinoids” the agenda of clinicians.Disclosure of interestThe authors have not supplied their declaration of competing interest.

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