ArticleACS chemical neuroscience2013
The synthesis and pharmacological evaluation of adamantane-derived indoles: cannabimimetic drugs of abuse.
Article in ACS chemical neuroscience, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
24 citing papers in PubMed, 86 citations in OpenAlex.
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- Timeframe Analysis of Novel Synthetic Cannabinoids Effects: A Study on Behavioral Response and Endogenous Cannabinoids Disruption.International journal of molecular sciences · 2024Article
- Acute Cardiovascular and Cardiorespiratory Effects of JWH-018 in Awake and Freely Moving Mice: Mechanism of Action and Possible Antidotal Interventions?International journal of molecular sciences · 2023Article
- The Old and the New: Cardiovascular and Respiratory Alterations Induced by Acute JWH-018 Administration Compared to ΔInternational journal of molecular sciences · 2023Article
- Why Do Marijuana and Synthetic Cannabimimetics Induce Acute Myocardial Infarction in Healthy Young People?Cells · 2022Review
- Synthesis, Molecular Pharmacology, and Structure-Activity Relationships of 3-(Indanoyl)indoles as Selective Cannabinoid Type 2 Receptor Antagonists.Journal of medicinal chemistry · 2021Article
- Molecular Pharmacology of Synthetic Cannabinoids: Delineating CB1 Receptor-Mediated Cell Signaling.International journal of molecular sciences · 2020Review
- Comprehensive Protocol for the Identification and Characterization of New Psychoactive Substances in the Service of Law Enforcement Agencies.Frontiers in chemistry · 2020Article
- Metabolic Profiling of a CB2 Agonist, AM9338, Using LC-MS and Microcoil-NMR: Identification of a Novel Dihydroxy Adamantyl Metabolite.Frontiers in pharmacology · 2020Article
- In vitro determination of the efficacy of illicit synthetic cannabinoids at CBBritish journal of pharmacology · 2019Article
- Potential Mechanisms Underlying the Deleterious Effects of Synthetic Cannabinoids Found in Spice/K2 Products.Brain sciences · 2019Review
- Enantiospecific Synthesis, Chiral Separation, and Biological Activity of Four Indazole-3-Carboxamide-Type Synthetic Cannabinoid Receptor Agonists and Their Detection in Seized Drug Samples.Frontiers in chemistry · 2019Article
- Advances in the Development of PET Ligands Targeting Histone Deacetylases for the Assessment of Neurodegenerative Diseases.Molecules (Basel, Switzerland) · 2018Review
- Repeated Exposure to the "Spice" Cannabinoid JWH-018 Induces Tolerance and Enhances Responsiveness to 5-HTFrontiers in psychiatry · 2018Article
- Characterization of structurally novel G protein biased CBPharmacological research · 2017Article
- Synthetic cannabinoids found in "spice" products alter body temperature and cardiovascular parameters in conscious male rats.Drug and alcohol dependence · 2017Article
- In vitro and in vivo pharmacokinetics and metabolism of synthetic cannabinoids CUMYL-PICA and 5F-CUMYL-PICA.Forensic toxicology · 2017Article
- Combination Chemistry: Structure-Activity Relationships of Novel Psychoactive Cannabinoids.Current topics in behavioral neurosciences · 2017Review
- Acute myocardial infarction, associated with the use of a synthetic adamantyl-cannabinoid: a case report.BMC pharmacology & toxicology · 2016Article
- The 2-alkyl-2Forensic toxicology · 2016Article
Corrections and comments
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Authors and funding
13 authors at 4 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Two novel adamantane derivatives, adamantan-1-yl(1-pentyl-1H-indol-3-yl)methanone (AB-001) and N-(adamtan-1-yl)-1-pentyl-1H-indole-3-carboxamide (SDB-001), were recently identified as cannabimimetic indoles of abuse. Conflicting anecdotal reports of the psychoactivity of AB-001 in humans, and a complete dearth of information about the bioactivity of SDB-001, prompted the preparation of AB-001, SDB-001, and several analogues intended to explore preliminary structure-activity relationships within this class. This study sought to elucidate which structural features of AB-001, SDB-001, and their analogues govern the cannabimimetic potency of these chemotypes in vitro and in vivo. All compounds showed similar full agonist profiles at CB1 (EC50 = 16-43 nM) and CB2 (EC50 = 29-216 nM) receptors in vitro using a FLIPR membrane potential assay, with the exception of SDB-002, which demonstrated partial agonist activity at CB2 receptors. The activity of AB-001, AB-002, and SDB-001 in rats was compared to that of Δ(9)-tetrahydrocannabinol (Δ(9)-THC) and cannabimimetic indole JWH-018 using biotelemetry. SDB-001 dose-dependently induced hypothermia and reduced heart rate (maximal dose 10 mg/kg) with potency comparable to that of Δ(9)-tetrahydrocannabinol (Δ(9)-THC, maximal dose 10 mg/kg), and lower than that of JWH-018 (maximal dose 3 mg/kg). Additionally, the changes in body temperature and heart rate affected by SDB-001 are of longer duration than those of Δ(9)-THC or JWH-018, suggesting a different pharmacokinetic profile. In contrast, AB-001, and its homologue, AB-002, did not produce significant hypothermic and bradycardic effects, even at relatively higher doses (up to 30 mg/kg), indicating greatly reduced potency compared to Δ(9)-THC, JWH-018, and SDB-001.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.