Journal ArticleDOI
Identification and quantitation of two cannabimimetic phenylacetylindoles JWH-251 and JWH-250, and four cannabimimetic naphthoylindoles JWH-081, JWH-015, JWH-200, and JWH-073 as designer drugs in illegal products
TLDR
In this paper, six cannabimimetic indoles have been identified as adulterants in herbal or chemical products being sold illegally in Japan, with four of the compounds being new as adulters to our knowledge.Abstract:
Six cannabimimetic indoles have been identified as adulterants in herbal or chemical products being sold illegally in Japan, with four of the compounds being new as adulterants to our knowledge The identifications were based on analyses using gas chromatography–mass spectrometry, liquid chromatography–mass spectrometry, high-resolution mass spectrometry, and nuclear magnetic resonance spectroscopy The first two compounds were identified as phenylacetyl indoles JWH-251 (2-(2-methylphenyl)-1-(1-pentyl-1H-indol-3-yl)ethanone; 1) and its demethyl-methoxylated analog JWH-250 (2-(2-methoxyphenyl)-1-(1-pentyl-1H-indol-3-yl)ethanone; 2) Compound 2 was identical to that found as an adulterant in the UK and in Germany in 2009 The third compound was naphthoylindole JWH-081 (1-(4-methoxynaphthalenyl)-(1-pentyl-1H-indol-3-yl)methanone; 3), and the fourth was JWH-073 (1-naphthalenyl(1-butyl-1H-indol-3-yl)methanone; 4), which had been identified as an adulterant in our previous study Two additional compounds were JWH-015 (1-naphthalenyl(2-methyl-1-propyl-1H-indol-3-yl)methanone; 5) and JWH-200 (1-naphthalenyl(1-(2-(4-morpholinyl)ethyl)-1H-indol-3-yl)methanone; 6) Compounds 1–4 and 6 were reported to be synthetic cannabinoids with selective affinity for cannabinoid CB1 receptors, while compound 5 was reported to be a selective CB2 receptor agonist causing immunosuppressive effects without psychotropic affects One product contained both CB1 and CB2 receptor agonists in our collection Quantitative analyses of the six cannabimimetic compounds in 20 products revealed that there was large variation in concentrations of the detected compounds among products; for herbal cutting products, the total amounts of these cannabinoids ranged from 26 to 100 mgread more
Citations
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Spice drugs are more than harmless herbal blends: a review of the pharmacology and toxicology of synthetic cannabinoids
TL;DR: A review of the legal status of common synthetic cannabinoids detected in Spice and analytical procedures used to test Spice products and human specimens collected under a variety of clinical circumstances is provided in this paper.
Journal ArticleDOI
Acute toxicity due to the confirmed consumption of synthetic cannabinoids: clinical and laboratory findings
TL;DR: Acute toxic symptoms associated with their use are also reported after intake of high doses of cannabis, but agitation, seizures, hypertension, emesis and hypokalaemia seem to be characteristic to the synthetic cannabinoids, which are high-affinity and high-efficacy agonists of the CB(1) receptor.
Journal ArticleDOI
Beyond THC: The New Generation of Cannabinoid Designer Drugs
TL;DR: An escalating number of compounds with cannabinoid receptor activity are currently being found as ingredients of Spice, of which almost nothing is known in terms of pharmacology, toxicology, and safety.
Journal ArticleDOI
A Characterization of Synthetic Cannabinoid Exposures Reported to the National Poison Data System in 2010
Christopher Hoyte,Jeena Jacob,Andrew A. Monte,Mohammed Al-Jumaan,Alvin C. Bronstein,Alvin C. Bronstein,Kennon Heard +6 more
TL;DR: Most exposures to Δ-9-tetrahydrocannabinol homologs resulted in non-life-threatening effects not requiring treatment, although a minority of exposures resulted in more severe effects, including seizures.
Journal ArticleDOI
Two new-type cannabimimetic quinolinyl carboxylates, QUPIC and QUCHIC, two new cannabimimetic carboxamide derivatives, ADB-FUBINACA and ADBICA, and five synthetic cannabinoids detected with a thiophene derivative α-PVT and an opioid receptor agonist AH-7921 identified in illegal products
TL;DR: In this paper, two new types of quinolinyl carboxylates, quinolin-8-yl 1-pentyl-(1H-indole)-3-carboxylate (QUCHIC) and quinoline-8 -yl 1-(cyclohexylmethyl)-1Hindole-3 -carboxylate (QUChIC, 2), were identified as designer drugs in illegal products.
References
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Journal ArticleDOI
'Spice' and other herbal blends: harmless incense or cannabinoid designer drugs?
Volker Auwärter,Sebastian Dresen,Wolfgang Weinmann,Michael Müller,Michael Pütz,Nerea Ferreirós +5 more
Journal Article
Evaluation of binding in a transfected cell line expressing a peripheral cannabinoid receptor (CB2): identification of cannabinoid receptor subtype selective ligands.
TL;DR: Although most of the chosen compounds did not discriminate between CB1 and CB2, several ligands were identified that showed selectivity and can now serve as a basis for the design of compounds with even greater selectivity.
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TL;DR: The biological activities, pharmacology, and signal transduction mechanisms for the cannabinoid receptors, with particular emphasis on the responses to the eicosanoid ligands are described.
Journal Article
Cannabinoid structure-activity relationships: correlation of receptor binding and in vivo activities.
David R. Compton,Rice Kc,B. R. De Costa,Raj K. Razdan,Lawrence S. Melvin,M R Johnson,Billy R. Martin +6 more
TL;DR: High correlations were demonstrated between binding affinity and in vivo potency in both the rat drug discrimination model and for psychotomimetic activity in humans, and the structure-activity relationship indicated the importance of side chain structure to high-affinity binding.
Journal ArticleDOI
Behavioral, biochemical, and molecular modeling evaluations of cannabinoid analogs.
Billy R. Martin,D R Compton,Brian F. Thomas,W. R. Prescott,P. J. Little,Raj K. Razdan,M R Johnson,L S Melvin,Raphael Mechoulam,S. J. Ward +9 more
TL;DR: The structural diversity and wide-ranging potencies of the analogs described herein provide the opportunity to develop a pharmacophore for the cannabinoids using molecular modeling techniques.