Neuropharmacological characterization of the new psychoactive substance methoxetamine

Neuropharmacology

Volumn 123, Issue , 2017, Pages 1-9

  Hondebrink, Laura ^a   Kasteel, Emma E J ^a,b   Tukker, Anke M ^b   Wijnolts, Fiona M J ^b   Verboven, Anouk H A ^b   Westerink, Remco H S ^b  

^a UNIVERSITY MEDICAL CENTER UTRECHT   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

Glutamatergic neurotransmission; Human induced pluripotent stem cell derived neurons; Ketamine; Methoxetamine; Monoamine transporters; Neuronal electrical activity

Indexed keywords

ACETYLCHOLINE; ADENOSINE TRIPHOSPHATE; DOPAMINE TRANSPORTER; GLUTAMIC ACID; KETAMINE; METHOXETAMINE; NORADRENALIN TRANSPORTER; POTASSIUM; PSYCHOTROPIC AGENT; SEROTONIN TRANSPORTER; UNCLASSIFIED DRUG; VOLTAGE GATED CALCIUM CHANNEL; 2-(3-METHOXYPHENYL)-2-(ETHYLAMINO)CYCLOHEXANONE; CALCIUM; CALCIUM CHANNEL; CARRIER PROTEIN; CYCLOHEXANONE DERIVATIVE; CYCLOHEXYLAMINE DERIVATIVE; DIVALENT CATION; GYK PROTEIN, RAT; VESICULAR MONOAMINE TRANSPORTER;

ANIMAL CELL; ARTICLE; ASTROCYTE; BRAIN CELL; CALCIUM CELL LEVEL; CALCIUM SIGNALING; CALCIUM TRANSPORT; CONTROLLED STUDY; HEK293 CELL LINE; HUMAN; HUMAN CELL; IC50; IN VITRO STUDY; INDUCED PLURIPOTENT STEM CELL; NONHUMAN; PRIORITY JOURNAL; RAT; ANALOGS AND DERIVATIVES; ANIMAL; BRAIN CORTEX; CELL CULTURE; COCULTURE; DRUG EFFECT; METABOLISM; NERVE CELL; PHYSIOLOGY; TUMOR CELL LINE; WISTAR RAT;

ANIMALS; CALCIUM; CALCIUM CHANNELS; CARRIER PROTEINS; CATIONS, DIVALENT; CELL LINE, TUMOR; CELLS, CULTURED; CEREBRAL CORTEX; COCULTURE TECHNIQUES; CYCLOHEXANONES; CYCLOHEXYLAMINES; GLUTAMIC ACID; HEK293 CELLS; HUMANS; INDUCED PLURIPOTENT STEM CELLS; KETAMINE; NEURONS; PSYCHOTROPIC DRUGS; RATS, WISTAR; VESICULAR MONOAMINE TRANSPORT PROTEINS;

EID: 85019605466     PISSN: 00283908     EISSN: 18737064     Source Type: Journal    
DOI: 10.1016/j.neuropharm.2017.04.035     Document Type: Article

References (45)

1. Bergman, S.A., Ketamine: review of its pharmacology and its use in pediatric anesthesia. Anesth. Prog. 46 (1999), 10–20.
2. Coates, K.M., Flood, P., Ketamine and its preservative, benzethonium chloride, both inhibit human recombinant alpha7 and alpha4beta2 neuronal nicotinic acetylcholine receptors in Xenopus oocytes. Br. J. Pharmacol. 134 (2001), 871–879, 10.1038/sj.bjp.0704315.
3. Corazza, O., Assi, S., Schifano, F., From “Special K” to “Special M”: the evolution of the recreational use of ketamine and methoxetamine. CNS Neurosci. Ther. 19 (2013), 454–460, 10.1111/cns.12063.
4. Corazza, O., Schifano, F., Simonato, P., Fergus, S., Assi, S., Stair, J., Corkery, J., Trincas, G., Deluca, P., Davey, Z., Blaszko, U., Demetrovics, Z., Moskalewicz, J., Enea, A., di Melchiorre, G., Mervo, B., di Furia, L., Farre, M., Flesland, L., Pasinetti, M., Pezzolesi, C., Pisarska, A., Shapiro, H., Siemann, H., Skutle, A., Enea, A., di Melchiorre, G., Sferrazza, E., Torrens, M., van der Kreeft, P., Zummo, D., Scherbaum, N., Phenomenon of new drugs on the Internet: the case of ketamine derivative methoxetamine. Hum. Psychopharmacol. 27 (2012), 145–149, 10.1002/hup.1242.
5. Dargan, P.I., Tang, H.C., Liang, W., Wood, D.M., Yew, D.T., Three months of methoxetamine administration is associated with significant bladder and renal toxicity in mice. Clin. Toxicol. 52 (2014), 176–180, 10.3109/15563650.2014.892605.
6. de Groot, M.W.G.D.M., van Kleef, R.G.D.M., de Groot, A., Westerink, R.H.S., In vitro developmental neurotoxicity following chronic exposure to 50 Hz extremely low-frequency electromagnetic fields in primary rat cortical cultures. Toxicol. Sci. 149 (2016), 433–440, 10.1093/toxsci/kfv242.
7. Dingemans, M.M.L., Schütte, M.G., Wiersma, D.M.M., de Groot, A., van Kleef, R.G.D.M., Wijnolts, F.M.J., Westerink, R.H.S., Chronic 14-day exposure to insecticides or methylmercury modulates neuronal activity in primary rat cortical cultures. Neurotoxicology 57 (2016), 194–202, 10.1016/j.neuro.2016.10.002.
8. Elliott, J.M., Beveridge, T.J., Psychostimulants and monoamine transporters: upsetting the balance. Curr. Opin. Pharmacol. 5:1 (2005), 94–100.
9. EMCDDA, European Drug Report 2016: Trends and Developments., 2016, 10.2810/04312.
10. EMCDDA, Europol, EMCDDA | EMCDDA–Europol Joint Report on a New Psychoactive Substance: Methoxetamine (2-(3-methoxyphenyl)-2-(ethylamino)cyclohexanone)., 2014, 10.2810/28543.
11. Europol, EU Drugs Markets Report: a Strategic Analysis., 2013, 10.2810/85143.
12. van der Gouwe, D., DIMS Jaarbericht 2014. 2014, Trimbos Institute Accessed via https://assets.trimbos.nl/docs/dcd6beec-29e2-4488-b76f-3118f74b8643.pdf.
13. Hatakeyama, N., Yamazaki, M., Shibuya, N., Yamamura, S., Momose, Y., Effects of ketamine on voltage-dependent calcium currents and membrane potentials in single bullfrog atrial cells. J. Anesth. 15:3 (2001), 149–153, 10.1007/S005400170017.
14. Hondebrink, L., Meulenbelt, J., Meijer, M., Van Den Berg, M., Westerink, R.H.S., High concentrations of MDMA (’ecstasy') and its metabolite MDA inhibit calcium influx and depolarization-evoked vesicular dopamine release in PC12 cells. Neuropharmacology 61 (2011), 202–208, 10.1016/j.neuropharm.2011.03.028.
15. Hondebrink, L., Meulenbelt, J., van Kleef, R.G.D.M., van den Berg, M., Westerink, R.H.S., Modulation of human GABAA receptor function: a novel mode of action of drugs of abuse. Neurotoxicology 32 (2011), 823–827, 10.1016/j.neuro.2011.05.016.
16. Hondebrink, L., Meulenbelt, J., Rietjens, S.J., Meijer, M., Westerink, R.H.S., Methamphetamine, amphetamine, MDMA (’ecstasy'), MDA and mCPP modulate electrical and cholinergic input in PC12 cells. Neurotoxicology 33 (2012), 255–260, 10.1016/j.neuro.2011.09.003.
17. Hondebrink, L., Nugteren-van Lonkhuyzen, J.J., van Der Gouwe, D., Brunt, T.M., Monitoring new psychoactive substances (NPS) in The Netherlands: data from the drug market and the poisons information centre. Drug Alcohol Depend. 147 (2015), 109–115, 10.1016/j.drugalcdep.2014.11.033.
18. Hondebrink, L., Verboven, A.H.A., Drega, W.S., Schmeink, S., de Groot, M.W.G.D.M., van Kleef, R.G.D.M., Wijnolts, F.M.J., de Groot, A., Meulenbelt, J., Westerink, R.H.S., Neurotoxicity screening of (illicit) drugs using novel methods for analysis of microelectrode array (MEA) recordings. Neurotoxicology 55 (2016), 1–9, 10.1016/j.neuro.2016.04.020.
19. Horsley, R.R., Lhotkova, E., Hajkova, K., Jurasek, B., Kuchar, M., Palenicek, T., Detailed pharmacological evaluation of methoxetamine (MXE), a novel psychoactive ketamine analogue—Behavioural, pharmacokinetic and metabolic studies in the Wistar rat. Brain Res. Bull., 2016, 10.1016/j.brainresbull.2016.05.002.
20. Hysek, C.M., Simmler, L.D., Nicola, V.G., Vischer, N., Donzelli, M., Krähenbühl, S., Grouzmann, E., Huwyler, J., Hoener, M.C., Liechti, M.E., Duloxetine inhibits effects of MDMA (“ecstasy”) in vitro and in humans in a randomized placebo-controlled laboratory study. PLoS One, 7, 2012, e36476, 10.1371/journal.pone.0036476.
21. Johnstone, A.F.M., Gross, G.W., Weiss, D.G., Schroeder, O.H.U., Gramowski, A., Shafer, T.J., Microelectrode arrays: a physiologically based neurotoxicity testing platform for the 21st century. Neurotoxicology, 2010, 10.1016/j.neuro.2010.04.001.
22. Kasteel, E.E.J., Westerink, R.H.S., Comparison of the acute inhibitory effects of Tetrodotoxin (TTX) in rat and human neuronal networks for risk assessment purposes. Toxicol. Lett. 270 (2017), 12–16, 10.1016/j.toxlet.2017.02.014.
23. Köles, L., Kató, E., Hanuska, A., Zádori, Z.S., Al-Khrasani, M., Zelles, T., Rubini, P., Illes, P., Modulation of excitatory neurotransmission by neuronal/glial signalling molecules: interplay between purinergic and glutamatergic systems. Purinergic Signal 12 (2016), 1–24, 10.1007/s11302-015-9480-5.
24. Lawn, W., Borschmann, R., Cottrell, A., Winstock, A., Methoxetamine: prevalence of use in the USA and UK and associated urinary problems. J. Subst. Use, 2014, 1–6, 10.3109/14659891.2014.966345.
25. Linsen, F., Koning, R.P.J., van Laar, M., Niesink, R.J.M., Koeter, M.W., Brunt, T.M., 4-Fluoroamphetamine in The Netherlands: more than a one-night stand. Addiction 110 (2015), 1138–1143, 10.1111/add.12932.
26. Meyer, D.A., Carter, J.M., Johnstone, A.F.M., Shafer, T.J., Pyrethroid modulation of spontaneous neuronal excitability and neurotransmission in hippocampal neurons in culture. Neurotoxicology 29 (2008), 213–225, 10.1016/j.neuro.2007.11.005.
27. Nishimura, M., Sato, K., Okada, T., Yoshiya, I., Schloss, P., Shimada, S., Tohyama, M., Ketamine inhibits monoamine transporters expressed in human embryonic kidney 293 cells. Anesthesiology 88 (1998), 768–774.
28. Odawara, A., Katoh, H., Matsuda, N., Suzuki, I., Physiological maturation and drug responses of human induced pluripotent stem cell-derived cortical neuronal networks in long-term culture. Sci. Rep., 6, 2016, 26181, 10.1038/srep26181.
29. Parsons, C.G., Panchenko, V.A., Pinchenko, V.O., Tsyndrenko, A.Y., Krishtal, O.A., Comparative patch-clamp studies with freshly dissociated rat hippocampal and striatal neurons on the NMDA receptor antagonistic effects of amantadine and memantine. Eur. J. Neurosci. 8 (1996), 446–454.
30. Roth, B.L., Gibbons, S., Arunotayanun, W., Huang, X.-P., Setola, V., Treble, R., Iversen, L., The ketamine analogue methoxetamine and 3- and 4-methoxy analogues of phencyclidine are high affinity and selective ligands for the glutamate NMDA receptor. PLoS One, 8, 2013, e59334, 10.1371/journal.pone.0059334.
31. Rothman, R.B., Baumann, M.H., Monoamine transporters and psychostimulant drugs. Eur. J. Pharmacol. 479:1–3 (2003), 23–40.
32. Shinde, V., Sureshkumar, P., Sotiriadou, I., Hescheler, J., Sachinidis, A., Human embryonic and induced pluripotent stem cell based toxicity testing models: future applications in new drug discovery. Curr. Med. Chem. 23:30 (2016), 3495–3509.
33. Simmler, L.D., Rickli, A., Hoener, M.C., Liechti, M.E., Monoamine transporter and receptor interaction profiles of a new series of designer cathinones. Neuropharmacology 79 (2014), 152–160.
34. Schmidt, B.Z., Lehmann, M., Gutbier, S., Nembo, E., Noel, S., Smirnova, L., Forsby, A., Hescheler, J., Avci, H.X., Hartung, T., Leist, M., Kobolák, J., Dinnyés, A., In vitro acute and developmental neurotoxicity screening: an overview of cellular platforms and high-throughput technical possibilities. Arch. Toxicol. 91:1 (2017), 1–33, 10.1007/s00204-016-1805-9.
35. Sofroniew, M.V., Reactive astrocytes in neural repair and protection. Neuroscience 11:5 (2005), 400–407.
36. Tukker, A.M., Groot, M.W.G.D.M., De Wijnolts, F.M.J., Emma, E.J., Hondebrink, L., Westerink, R.H.S., Is the time right for in vitro neurotoxicity testing using human iPSC-derived neurons. ALTEX 33 (2016), 261–271, 10.14573/altex.1510091.
37. Vassallo, A., Chiappalone, M., De Camargos Lopes, R., Scelfo, B., Novellino, A., Defranchi, E., Palosaari, T., Weisschu, T., Ramirez, T., Martinoia, S., Johnstone, A.F.M., Mack, C.M., Landsiedel, R., Whelan, M., Bal-Price, A., Shafer, T.J., A multi-laboratory evaluation of microelectrode array-based measurements of neural network activity for acute neurotoxicity testing. Neurotoxicology, 2016, 10.1016/j.neuro.2016.03.019.
38. Verrico, C.D., Miller, G.M., Madras, B.K., MDMA (Ecstasy) and human dopamine, norepinephrine, and serotonin transporters: implications for MDMA-induced neurotoxicity and treatment. Psychopharmacol. Berl. 189:4 (2007), 489–503.
39. Wang, C., Application of in vitro models in developmental neurotoxicity and pharmaceutics research. J. Mol. Pharm. Org. Process Res., 3, 2015, e122, 10.4172/2329-9053.1000e122.
40. 2+ channels in porcine tracheal smooth muscle cells. Anesthesiology 83 (1995), 1274–1282, 10.1097/00000542-199512000-00018.
41. Yamakura, T., Mori, H., Masaki, H., Shimoji, K., Mishina, M., Different sensitivities of NMDA receptor channel subtypes to non-competitive antagonists. Neuroreport 4 (1993), 687–690.
42. Yamakura, T., Chavez-Noriega, L.E., Harris, R.A., Subunit-dependent inhibition of human neuronal nicotinic acetylcholine receptors and other ligand-gated ion channels by dissociative anesthetics ketamine and dizocilpine. Anesthesiology 92 (2000), 1144–1153, 10.1097/00000542-200004000-00033.
43. Zanda, M.T., Fadda, P., Chiamulera, C., Fratta, W., Fattore, L., Methoxetamine, a novel psychoactive substance with serious adverse pharmacological effects: a review of case reports and preclinical findings. Behav. Pharmacol., 2016, 1–8, 10.1097/FBP.0000000000000241.
44. Zawilska, J.B., Methoxetamine – a novel recreational drug with potent hallucinogenic properties. Toxicol. Lett. 230 (2014), 402–407, 10.1016/j.toxlet.2014.08.011.
45. Zwartsen, A., Verboven, A.H.A., van Kleef, R.G.D.M., Wijnolts, F.M.J., Westerink, R.H.S., Hondebrink, L., Measuring inhibition of monoamine reuptake transporters by new psychoactive substances in real-time using a high-throughput, fluorescence-based assay. Toxicol. In Vitro, 2017 (in press) http://dx.doi.org/10.1016/j.tiv.2017.05.010.