Effects of aromatic ring-substituted phenethylamines on the release of dopamine and serotonin
Tóm tắt
Significant disturbances of the classical amphetamines on the dopamine (DA) and serotonin (5-HT) systems have been previously reported. However, few studies have been conducted on the effects of new psychoactive phenethylamines on the release of DA and 5-HT. In the present study, the effects of new psychoactive phenethylamines with a variety of aromatic ring substitutions (5-API, 3-FMA, 5-MAPB, and DMMA) on the release of DA and 5-HT were investigated. Changes of DA, 5-HT and their metabolites in brain microdialysates from rats following exposure to the drugs were examined using a validated liquid chromatography–tandem mass spectrometry method. Their potencies of DA and 5-HT uptake inhibition as well as dopamine transporter (DAT) and serotonin transporter (SERT) binding were also determined. With the exception of DMMA, the drugs markedly affected the extracellular concentration of DA, 5-HT and/or their metabolites in rats and acted as potent inhibitors for DAT and/or SERT. Especially, 5-API potently induced the nonselective release of both DA and 5-HT, which was strongly correlated with a high degree of uptake inhibition and binding affinity to DAT and SERT. The 3-FMA, a methamphetamine analog with a halogen-substituted benzene, induced greater 5-HT release than DA. We found that new psychoactive phenethylamines, with a variety of aromatic ring substitutions, affected the extracellular levels of DA, 5-HT, and/or their metabolites in the nucleus accumbens of rats to varying degrees and in different ways. The current results may assist further research into monoamine neurotransmitter-related mechanisms of new psychoactive phenethylamines.
Tài liệu tham khảo
Kersten BP, McLaughlin ME (2015) Toxicology and management of novel psychoactive drugs. J Pharm Pract 28:50–65. https://doi.org/10.1177/0897190014544814
Nelson ME, Bryant SM, Aks SE (2014) Emerging drugs of abuse. Dis Mon 60:110–132. https://doi.org/10.1016/j.disamonth.2014.01.001
Rivera JV, Vance EG, Rushton WF, Arnold JK (2017) Novel psychoactive substances and trends of abuse. Crit Care Nurs Q 40:374–382. https://doi.org/10.1097/CNQ.0000000000000174
Hill SL, Thomas SH (2011) Clinical toxicology of newer recreational drugs. Clin Toxicol 49:705–719. https://doi.org/10.3109/15563650.2011.615318
Gingrich JA, Hen R (2001) Dissecting the role of the serotonin system in neuropsychiatric disorders using knockout mice. Psychopharmacology 155:1–10 (PMID: 11374326)
Sanders-Bush E, Hazelwood L (2011) 5-Hydroxytryptamine (serotonin) and dopamine. In: Brunton LL, Chabner BA, Knollmann BC (eds) Goodman & Gilman’s pharmacological basis of therapeutics, 12th edn. McGraw-Hill, New York, pp 335–361
Courtney KE, Ray LA (2014) Methamphetamine: an update on epidemiology, pharmacology, clinical phenomenology, and treatment literature. Drug Alcohol Depend 143:11–21. https://doi.org/10.1016/j.drugalcdep.2014.08.003
Lyles J, Cadet JL (2003) Methylenedioxymethamphetamine (MDMA, Ecstasy) neurotoxicity: cellular and molecular mechanisms. Brain Res Rev 42:155–168 (PMID: 12738056)
Kim M, Kim DH, Lee YS, Jang C-G, Yang CH, Lee S (2017) Changes in dopamine, serotonin and their metabolites in brain microdialysates from rats following exposure to new psychoactive drugs. Forensic Toxicol 35:66–76. https://doi.org/10.1007/s11419-016-0335-8
Zhao RJ, Yoon SS, Lee BH, Kwon YK, Kim KJ, Shim I, Choi K-H, Kim MR, Golden GT, Yang CH (2006) Acupuncture normalizes the release of accumbal dopamine during the withdrawal period and after the ethanol challenge in chronic ethanol-treated rats. Neurosci Lett 395:28–32. https://doi.org/10.1016/j.neulet.2005.10.043
Kim M, Lee JG, Yang CH, Lee S (2016) Silica stationary phase-based on-line sample enrichment coupled with LC–MS/MS for the quantification of dopamine, serotonin and their metabolites in rat brain microdialysates. Anal Chim Acta 923:55–65. https://doi.org/10.1016/j.aca.2016.03.021
Paudel S, Cao Y, Guo S, An B, Kim KM, Cheon SH (2015) Design and synthesis of 4-benzylpiperidine carboxamides as dual serotonin and norepinephrine reuptake inhibitors. Bioorg Med Chem 23:6418–6426. https://doi.org/10.1016/j.bmc.2015.08.022
Torres GE, Yao WD, Mohn AR, Quan H, Kim KM, Levey AI, Staudinger J, Caron MG (2001) Functional interaction between monoamine plasma membrane transporters and the synaptic PDZ domain-containing protein PICK1. Neuron 30:121–134 (PMID: 11343649)
Wigestrand MB, Stenberg M, Walaas SI, Fonnum F, Andersson PL (2013) Non-dioxin-like PCBs inhibit [3H]WIN-35,428 binding to the dopamine transporter: a structure-activity relationship study. Neurotoxicology 39:18–24. https://doi.org/10.1016/j.neuro.2013.07.005
Kim Y, Tae J, Lee K, Rhim H, Choo IH, Cho H, Park W-K, Keum G, Choo H (2014) Novel N-biphenyl-2-ylmethyl 2-methoxyphenylpiperazinylalkanamides as 5-HT7R antagonists for the treatment of depression. Bioorg Med Chem 22:4587–4596. https://doi.org/10.1016/j.bmc.2014.07.026
Brinkø A, Larsen MT, Koldsø H, Besenbacher L, Kolind A, Schiøtt B, Sinning S, Jensen HH (2016) Synthesis and inhibitory evaluation of 3-linked imipramines for the exploration of the S2 site of the human serotonin transporter. Bioorg Med Chem 24:2725–2738. https://doi.org/10.1016/j.bmc.2016.04.039
Marusich JA, Antonazzo KR, Blough BE, Brandt SD, Kavanagh PV, Partilla JS, Baumann MH (2016) The new psychoactive substances 5-(2-aminopropyl)indole (5-IT) and 6-(2-aminopropyl)indole (6-IT) interact with monoamine transporters in brain tissue. Neuropharmacology 101:68–75. https://doi.org/10.1016/j.neuropharm.2015.09.004
Luethi D, Kolaczynska KE, Docci L, Krahenbuhl S, Hoener MC, Liechti ME (2017) Pharmacological profile of mephedrone analogs and related new psychoactive substances. Neuropharmacology 134:4–12. https://doi.org/10.1016/j.neuropharm.2017.07.026
Shimshoni JA, Winkler I, Golan E, Nutt D (2017) Neurochemical binding profiles of novel indole and benzofuran MDMA analogues. Naunyn Schmiedebergs Arch Pharmacol 390:15–24. https://doi.org/10.1007/s00210-016-1297-4
Herraiz T, Brandt SD (2014) 5-(2-Aminopropyl)indole (5-IT): a psychoactive substance used for recreational purposes is an inhibitor of human monoamine oxidase (MAO). Drug Test Anal 6:607–613. https://doi.org/10.1002/dta.1530
Rickli A, Hoener MC, Liechti ME (2015) Monoamine transporter and receptor interaction profiles of novel psychoactive substances: para-halogenated amphetamines and pyrovalerone cathinones. Eur Neuropsychopharmacol 25:365–376. https://doi.org/10.1016/j.euroneuro.2014.12.012
Nguyen P-T, Shin E-J, Dang D-K, Tran H-Q, Jang C-G, Jeong JH, Lee YJ, Lee HJ, Lee YS, Yamada K, Nabeshima T, Kim H-C (2018) Role of dopamine D1 receptor in 3-fluoromethamphetamine-induced neurotoxicity in mice. Neurochem Int 113:69–84. https://doi.org/10.1016/j.neuint.2017.11.017
Fuwa T, Suzuki J, Tanaka T, Inomata A, Honda Y, Kodama T (2016) Novel psychoactive benzofurans strongly increase extracellular serotonin level in mouse corpus striatum. J Toxicol Sci 41:329–337. https://doi.org/10.2131/jts.41.329
Montgomery T, Buon C, Eibauer S, Guiry PJ, Keenan AK, McBean GJ (2007) Comparative potencies of 3,4-methylenedioxymethamphetamine (MDMA) analogues as inhibitors of [3H]noradrenaline and [3H]5-HT transport in mammalian cell lines. Br J Pharmacol 152:1121–1130. https://doi.org/10.1038/sj.bjp.0707473