Off-target activity of NBOMes and NBOMe analogs at the µ opioid receptor

Åstrand A, Guerrieri D, Vikingsson S et al (2020) In vitro characterization of new psychoactive substances at the μ-opioid, CB1, 5HT1A, and 5-HT2A receptors-on-target receptor potency and efficacy, and off-target effects. Forensic Sci Int 317:110553. https://doi.org/10.1016/j.forsciint.2020.110553

Article  CAS  PubMed  Google Scholar 

Bakayan A, Domingo B, Vaquero CF et al (2017) Fluorescent protein–photoprotein fusions and their applications in calcium imaging. Photochem Photobiol 93:448–465. https://doi.org/10.1111/php.12682

Article  CAS  PubMed  Google Scholar 

Braden MR, Parrish JC, Naylor JC, Nichols DE (2006) Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists. Mol Pharmacol 70:1956–1964. https://doi.org/10.1124/mol.106.028720

Article  CAS  PubMed  Google Scholar 

Cannaert A, Storme J, Franz F et al (2016) Detection and activity profiling of synthetic cannabinoids and their metabolites with a newly developed bioassay. Anal Chem 88:11476–11485. https://doi.org/10.1021/acs.analchem.6b02600

Article  CAS  PubMed  Google Scholar 

Cannaert A, Franz F, Auwärter V, Stove CP (2017) Activity-based detection of consumption of synthetic cannabinoids in authentic urine samples using a stable cannabinoid reporter system. Anal Chem 89:9527–9536. https://doi.org/10.1021/acs.analchem.7b02552

Article  CAS  PubMed  Google Scholar 

Cannaert A, Storme J, Hess C et al (2018a) Activity-based detection of cannabinoids in serum and plasma samples. Clin Chem 64:918–926. https://doi.org/10.1373/clinchem.2017.285361

Article  CAS  PubMed  Google Scholar 

Cannaert A, Vasudevan L, Friscia M et al (2018b) Activity-based concept to screen biological matrices for opiates and (synthetic) opioids. Clin Chem 64:1221–1229. https://doi.org/10.1373/clinchem.2018.289496

Article  CAS  PubMed  Google Scholar 

Charlton SJ, Vauquelin G (2010) Elusive equilibrium: the challenge of interpreting receptor pharmacology using calcium assays. Br J Pharmacol 161:1250–1265. https://doi.org/10.1111/j.1476-5381.2010.00863.x

Article  CAS  PubMed  PubMed Central  Google Scholar 

Connor M, Christie MJ (1999) Opioid receptor signalling mechanisms. Clin Exp Pharmacol Physiol 26:493–499. https://doi.org/10.1046/j.1440-1681.1999.03049.x

Article  CAS  PubMed  Google Scholar 

De Luca MA, Tocco G, Mostallino R et al (2022) Pharmacological characterization of novel synthetic opioids: Isotonitazene, metonitazene, and piperidylthiambutene as potent μ-opioid receptor agonists. Neuropharmacology 221:109263. https://doi.org/10.1016/j.neuropharm.2022.109263

Article  CAS  PubMed  Google Scholar 

Deng L, Vysotski ES, Markova SV et al (2005) All three Ca2+-binding loops of photoproteins bind calcium ions: The crystal structures of calcium-loaded apo-aequorin and apo-obelin. Protein Sci 14:663–675. https://doi.org/10.1110/ps.041142905

Article  CAS  PubMed  PubMed Central  Google Scholar 

Dixon AS, Schwinn MK, Hall MP et al (2016) NanoLuc complementation reporter optimized for accurate measurement of protein interactions in cells. ACS Chem Biol 11:400–408. https://doi.org/10.1021/acschembio.5b00753

Article  CAS  PubMed  Google Scholar 

Domino EF (1986) Opioid-hallucinogen interactions. Pharmacol Biochem Behav 24:401–405. https://doi.org/10.1016/0091-3057(86)90370-9

Article  CAS  PubMed  Google Scholar 

Eshleman AJ, Forster MJ, Wolfrum KM et al (2014) Behavioral and neurochemical pharmacology of six psychoactive substituted phenethylamines: mouse locomotion, rat drug discrimination and in vitro receptor and transporter binding and function. Psychopharmacology 231:875–888. https://doi.org/10.1007/s00213-013-3303-6

Article  CAS  PubMed  Google Scholar 

Eshleman AJ, Wolfrum KM, Reed JF et al (2018) Neurochemical pharmacology of psychoactive substituted N-benzylphenethylamines: high potency agonists at 5-HT2A receptors. Biochem Pharmacol 158:27–34. https://doi.org/10.1016/j.bcp.2018.09.024

Article  CAS  PubMed  PubMed Central  Google Scholar 

Eshleman AJ, Nagarajan S, Wolfrum KM et al (2020) Affinity, potency, efficacy, selectivity, and molecular modeling of substituted fentanyls at opioid receptors. Biochem Pharmacol 182:114293. https://doi.org/10.1016/j.bcp.2020.114293

Article  CAS  PubMed  Google Scholar 

Ettrup A, Hansen M, Santini MA et al (2011) Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT2A agonist PET tracers. Eur J Nucl Med Mol Imaging 38:681–693. https://doi.org/10.1007/s00259-010-1686-8

Article  CAS  PubMed  Google Scholar 

European Monitoring Centre for Drugs and Drug Addiction (2014) Report on the risk assessment of 2-(4-iodo-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl) ethanamine (25I-NBOMe) in the framework of the Council Decision on new psychoactive substances. Luxembourg

European Monitoring Centre for Drugs and Drug Addiction (2022) European drug report: trends and developments 2022. Publications Office of the European Union, Luxembourg

Google Scholar 

Gillis A, Kliewer A, Kelly E et al (2020) Critical assessment of G protein-biased agonism at the μ-opioid receptor. Trends Pharmacol Sci 41:947–959. https://doi.org/10.1016/j.tips.2020.09.009

Article  CAS  PubMed  Google Scholar 

Glennon RA, Titeler M, McKenney JD (1984) Evidence for 5-HT2 involvement in the mechanism of action of hallucinogenic agents. Life Sci 35:2505–2511. https://doi.org/10.1016/0024-3205(84)90436-3

Article  CAS  PubMed  Google Scholar 

Greenwood JR, Calkins D, Sullivan AP, Shelley JC (2010) Towards the comprehensive, rapid, and accurate prediction of the favorable tautomeric states of drug-like molecules in aqueous solution. J Comput Aided Mol Des 24:591–604. https://doi.org/10.1007/s10822-010-9349-1

Article  CAS  PubMed  Google Scholar 

Halberstadt AL, Geyer MA (2011) Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology 61:364–381. https://doi.org/10.1016/j.neuropharm.2011.01.017

Article  CAS  PubMed  PubMed Central  Google Scholar 

Hansen M, Phonekeo K, Paine JS et al (2014) Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists. ACS Chem Neurosci 5:243–249. https://doi.org/10.1021/cn400216u

Article  CAS  PubMed  PubMed Central  Google Scholar 

Harder E, Damm W, Maple J et al (2016) OPLS3: a force field providing broad coverage of drug-like small molecules and proteins. J Chem Theory Comput 12:281–296. https://doi.org/10.1021/acs.jctc.5b00864

Article  CAS  PubMed  Google Scholar 

Huang W, Manglik A, Venkatakrishnan AJ et al (2015) Structural insights into µ-opioid receptor activation. Nature 524:315–321. https://doi.org/10.1038/nature14886

Article  CAS  PubMed  PubMed Central  Google Scholar 

Jensen AA, McCorvy JD, Leth-Petersen S et al (2017) Detailed characterization of the in vitro pharmacological and pharmacokinetic properties of N-(2-Hydroxybenzyl)-2,5-dimethoxy-4-cyanophenylethylamine (25CN-NBOH), a highly selective and brain-penetrant 5-HT2A receptor agonist. J Pharmacol Exp Ther 361:441–453. https://doi.org/10.1124/jpet.117.239905

Article  CAS  PubMed  Google Scholar 

Johnson MW, Hendricks PS, Barrett FS, Griffiths RR (2019) Classic psychedelics: an integrative review of epidemiology, therapeutics, mystical experience, and brain network function. Pharmacol Ther 197:83–102. https://doi.org/10.1016/j.pharmthera.2018.11.010

Article  CAS  PubMed  Google Scholar 

Keiser MJ, Setola V, Irwin JJ et al (2009) Predicting new molecular targets for known drugs. Nature 462:175–181. https://doi.org/10.1038/nature08506

Article  CAS  PubMed  PubMed Central  Google Scholar 

Kyriakou C, Marinelli E, Frati P et al (2015) NBOMe: new potent hallucinogens – pharmacology, analytical methods, toxicities, fatalities: a review. Eur Rev Med Pharmacol Sci 19:3270–3281

CAS  PubMed  Google Scholar 

Lipiński PFJ, Jarończyk M, DobrowolskiSadlej JCzJ (2019) Molecular dynamics of fentanyl bound to μ-opioid receptor. J Mol Model 25:144. https://doi.org/10.1007/s00894-019-3999-2

Article  CAS  PubMed  Google Scholar 

Luethi D, Liechti ME (2020) Designer drugs: mechanism of action and adverse effects. Arch Toxicol 94:1085–1133. https://doi.org/10.1007/s00204-020-02693-7

Article  CAS  PubMed  PubMed Central  Google Scholar 

Madhavi Sastry G, Adzhigirey M, Day T et al (2013) Protein and ligand preparation: parameters, protocols, and influence on virtual screening enrichments. J Comput Aided Mol Des 27:221–234. https://doi.org/10.1007/s10822-013-9644-8

Article  CAS  PubMed  Google Scholar 

Manglik A, Kruse AC, Kobilka TS et al (2012) Crystal structure of the µ-opioid receptor bound to a morphinan antagonist. Nature 485:321–326. https://doi.org/10.1038/nature10954

Article  CAS  PubMed  PubMed Central  Google Scholar 

Marek GJ (2003) Behavioral evidence for μ-opioid and 5-HT2A receptor interactions. Eur J Pharmacol 474:77–83. https://doi.org/10.1016/S0014-2999(03)01971-X

Article  CAS  PubMed  Google Scholar 

Nichols DE (2004) Hallucinogens. Pharmacol Ther 101:131–181. https://doi.org/10.1016/j.pharmthera.2003.11.002

Article 

留言 (0)

沒有登入
gif