scholarly journals The isolation and characterisation of the synthetic cannabinoid AM-2201 from commercial products using purification by HPLC-DAD

2015 ◽  
Vol 2 (1) ◽  
Author(s):  
Smilja Duranovic ◽  
Mathieu Elie ◽  
Mark Baron

AbstractA total of six products containing legal highs were purchased via the internet from the UK- based retailers and screened for the presence of synthetic cannabinoids using a fast GC-MS method and identified, in the absence of reference materials, by comparing the mass spectra with the Scientific Working Group for the Analysis of Seized Drugs (SWGDRUG) mass spectral library. Four synthetic cannabinoids were detected: RCS-4, CP-47, 497, UR-144 and AM-2201. The active ingredient (1-(5-fluoropentyl)-3-(1-naphthoyl) indole), with the street name AM-2201, detected in the product named Doob was isolated and purified from the methanolic extract of the product using preparative HPLC with analytical column (column overloading method). The structure of the substance was confirmed using NMR. This approach used common analytical equipment found in forensic and other analytical laboratories (except for the NMR), therefore can be useful for the identification of unknown psychoactive substances in drugs of abuse.

2020 ◽  
Vol 44 (7) ◽  
pp. 697-707
Author(s):  
Kelly Francisco da Cunha ◽  
Karina Diniz Oliveira ◽  
Marilyn A Huestis ◽  
Jose Luiz Costa

Abstract New psychoactive substances (NPS) are a major public health problem, primarily due to the increased number of acute poisoning cases. Detection of these substances is a challenge. The aim of this research was to develop and validate a sensitive screening method for 104 drugs of abuse, including synthetic cannabinoids, synthetic cathinones, fentanyl analogues, phenethylamines and other abused psychoactive compounds (i.e., THC, MDMA, LSD and their metabolites) in oral fluid by liquid chromatography–tandem mass spectrometry (LC–MS-MS). The Quantisal™ oral fluid device was used to collect oral fluid samples. The oral fluid–elution buffer mixture (500-μL sample) was extracted with t-butyl methyl ether, and chromatographic separation was performed on a Raptor™ biphenyl column (100 × 2.1 mm ID, 2.7 μm), with a total run time of 13.5 min. Limits of detection were established at three concentrations (0.05, 0.1 or 1 ng/mL) for most analytes, except for acetyl norfentanyl and mescaline (5 ng/mL). Matrix effects were generally <20% and overall extraction recoveries >60%. The highest matrix effect was observed within the synthetic cannabinoid group (PB22, −55.5%). Lower recoveries were observed for 2C-T (47.2%) and JWH-175 (58.7%). Recoveries from the Quantisal™ device were also evaluated for all analytes (56.7–127%), with lower recoveries noted for 25I-NBOMe, valerylfentanyl and mCPP (56.7, 63.0 and 69.9%, respectively). Drug stability in oral fluid was evaluated at 15, 60 and 90 days and at 25, 4 and −20°C. As expected, greater stability was observed when samples were stored at −20°C, but even when frozen, some NPS (e.g., synthetic cannabinoids) showed more than 20% degradation. The method was successfully applied to the analysis of seven authentic oral fluid samples positive for 17 different analytes. The method achieved good sensitivity and simultaneous detection of a wide range of NPS.


2020 ◽  
Vol 10 (9) ◽  
pp. 606
Author(s):  
Liana Fattore ◽  
Matteo Marti ◽  
Rafaela Mostallino ◽  
Maria Paola Castelli

Sex and gender deeply affect the subjective effects and pharmaco-toxicological responses to drugs. Men are more likely than women to use almost all types of illicit drugs and to present to emergency departments for serious or fatal intoxications. However, women are just as likely as men to develop substance use disorders, and may be more susceptible to craving and relapse. Clinical and preclinical studies have shown important differences between males and females after administration of “classic” drugs of abuse (e.g., Δ9-tetrahydrocannabinol (THC), morphine, cocaine). This scenario has become enormously complicated in the last decade with the overbearing appearance of the new psychoactive substances (NPS) that have emerged as alternatives to regulated drugs. To date, more than 900 NPS have been identified, and can be catalogued in different pharmacological categories including synthetic cannabinoids, synthetic stimulants (cathinones and amphetamine-like), hallucinogenic phenethylamines, synthetic opioids (fentanyls and non-fentanyls), new benzodiazepines and dissociative anesthetics (i.e., methoxetamine and phencyclidine-derivatives). This work collects the little knowledge reached so far on the effects of NPS in male and female animal and human subjects, highlighting how much sex and gender differences in the effects of NPS has yet to be studied and understood.


Author(s):  
Lea Wagmann ◽  
Tanja M. Gampfer ◽  
Markus R. Meyer

AbstractThe still increasing number of drugs of abuse, particularly the so-called new psychoactive substances (NPS), poses an analytical challenge for clinical and forensic toxicologists but also for doping control. NPS usually belong to various classes such as synthetic cannabinoids, phenethylamines, opioids, or benzodiazepines. Like other xenobiotics, NPS undergo absorption, distribution, metabolism, and excretion processes after consumption, but only very limited data concerning their toxicokinetics and safety properties is available once they appear on the market. The inclusion of metabolites in mass spectral libraries is often crucial for the detection of NPS especially in urine screening approaches. Authentic human samples may represent the gold standard for identification of metabolites but are often not available and clinical studies cannot be performed due to ethical concerns. However, numerous alternative in vitro and in vivo models are available. This trends article will give an overview on selected models, discuss current studies, and highlight recent developments.


Author(s):  
Loretta T Ford ◽  
Jonathan D Berg

Introduction Novel psychotropic substances also known as legal highs are a major concern in UK prisons, fuelling violence and putting a strain on resources for inmates requiring medical treatment for adverse effects. We provide a clinical toxicology service including routine screening for novel psychoactive substances. In 2015, we were approached by Her Majesty Prison Service search dog training team to advise on which novel psychoactive substances to target, and again in 2016 to further provide analytical support to test five letters which the dogs positively identified for novel psychotropic substances during routine searches of prison mail rooms. Here we provide the first analytical confirmation that letters sent to inmates are being used to smuggle novel psychotropic substances into UK prisons. Results Novel psychotropic substances were detected on all five letters and these included the stimulants ethylphenidate, methiopropamine and methoxiphenidaine, the sedative etizolam and the third generation synthetic cannabinoids 5F-AKB-48, AB-FUBINACA, MDMB-CHMICA. Other compounds detected include the class A drug cocaine, class B drug methylphenidate and the cutting agents lignocaine, benzocaine and procaine. Conclusion Novel psychotropic substances smuggled into UK prisons is a major safety and security concern. By analytically confirming letters sent to inmates do contain novel psychotropic substances, we have produced categorical evidence to support anecdotal suggestions that novel psychotropic substances are entering UK prisons in this manner.


Author(s):  
Loretta T Ford ◽  
Jonathan D Berg

Introduction Legal highs also known as novel psychoactive substances mimic the effects of classic drugs of abuse. Challenges to developing screening services for novel psychoactive substances include identifying which novel psychoactive substances are available to target. Using new techniques such as exact mass time of flight can help identify common novel psychoactive substances to target for screening patient samples by routine methods such as tandem mass spectrometry. We demonstrate this strategy working in our own clinical toxicology laboratory after qualitative analysis of 98 suspect materials for novel psychoactive substances by ultra-performance liquid chromatography with time of flight mass spectrometry. Results From July 2014 to July 2015 we received 98 requests to test a range of different suspect materials for novel psychoactive substances including herbs, tobacco, liquids, pills and powders. Overall, 87% of the suspect materials tested positive for novel psychoactive substances, and 15% for controlled drugs. Three common novel psychoactive substances were present in 74% of the suspect materials: methiopropamine, a methamphetamine analogue; ethylphenidate, a cocaine mimic; and the third generation synthetic cannabinoid 5F-AKB-48. For the 55 branded products we tested only 24% of the stated contents matched exactly the compounds we detected. Conclusion Testing suspect materials using ultra-performance liquid chromatography with time of flight mass spectrometry has identified three common novel psychoactive substances in use in the UK, simplifying the development of a relevant novel psychoactive substances screening service to our population. By incorporating this into our routine liquid chromatography tandem mass spectrometry drugs of abuse screen, then offers a clinically relevant novel psychoactive substances service to our users. This strategy ensures our clinical toxicology service continues to remain effective to meet the challenges of the changing drug use in the UK.


Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 793
Author(s):  
Emmanouil D. Tsochatzis ◽  
Joao Alberto Lopes ◽  
Margaret V. Holland ◽  
Fabiano Reniero ◽  
Giovanni Palmieri ◽  
...  

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.


BMC Chemistry ◽  
2021 ◽  
Vol 15 (1) ◽  
Author(s):  
Fariba Heshmati Afshar ◽  
Masumeh Zadehkamand ◽  
Zahra Rezaei ◽  
Abbas Delazar ◽  
Vahideh Tarhriz ◽  
...  

Abstract Background Artemisia splendens from the Asteraceae family is a new source of biologically active compounds. The current study investigated to evaluate antimicrobial and cytotoxicity activity of methanolic extracts and their fractions obtained from aerial parts by agar disk diffusion and MTT methods, respectively. The active fractions were subjected to preparative HPLC for isolating the pure compounds, which were structurally elucidated, by 1H and 13C NMR. Results The results showed that the methanolic extract and its 60% SPE fraction have the anti-proliferative activity on A549 cell line in comparison with the control group. Meanwhile, the methanolic extract and its 40% SPE fraction can inhibit the growth of Gram-positive strains as anti-microbial activity. The 60% SPE fraction also illustrated anti-proliferative activity on the HT-29 cell line compared to the control group. Chromatographic separations via preparative HPLC yielded 5 flavonoids and three flavonoid glycosides. Conclusion Based on the results it can be concluded that A. splendens as a potential source of cytotoxic and antimicrobial compounds can be used in pharmaceutics.


1997 ◽  
Vol 13 (2) ◽  
pp. 151-161 ◽  
Author(s):  
Kevin B. Thurbide ◽  
C. M. Elson ◽  
P. G. Sim

The negative‒ion chemical ionization mass spectra of a group of structural isomers of amphetamine have been studied using carbon dioxide as the reagent gas. Characteristic and reproducible differences are observed for each member of the set implying that this technique offers a means of distinguishing among groups of amphetamine isomers. Characteristic adducts to the molecular ion are observed in the form (M–[H]+[O]) and (M–[H]+[CO2]). Descriptions of some fragments are given based on the mass spectral behaviour of a set of analogue compounds and the results of oxygen-18 labelled carbon dioxide reagent gas experiments. Contents of the carbon dioxide plasma and their impact on various analytes is also discussed.


1972 ◽  
Vol 50 (16) ◽  
pp. 2707-2710 ◽  
Author(s):  
Larry Weiler

The mass spectra of several γ-substituted β-keto esters have been recorded and interpreted. The fragmentation patterns are compared to those of α-substituted β-keto esters and are found to be very useful in differentiating the α- and γ-substituted isomers. The mass spectral fragmentation schemes are dominated by cleavages α to the carbonyl groups and by McLafferty rearrangements.


2014 ◽  
Vol 284 ◽  
pp. 60-69
Author(s):  
Mariola Wicka ◽  
◽  
Piotr Chołbiński ◽  
Dorota Kwiatkowska ◽  
Andrzej Pokrywka ◽  
...  

Year on year, one can observe an increase in the use of addictive substances. This leads to occurring the problem of addiction as well as the use of psychoactive substances as a serious hazard to road users. The Regulation of the Minister of Health on agents acting similarly to alcohol and the conditions and manner of conducting research on their presence in the human body, requires adequate benchmarks for performing these tests. An importantfactor, from consultative point of view, is the knowledge of the chemical structure of substances belonging to different groups of drugs of abuse, their metabolic transformations that occur in the body as well as their influence on the body. This is to aid in the proper interpretation of the results of the analytical tests.


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