Hallucinogen-like effects of 2-([2-(4-cyano-2,5-dimethoxyphenyl) ethylamino]methyl)phenol (25CN-NBOH), a novel N-benzylphenethylamine with 100-fold selectivity for 5-HT2A receptors, in mice

Psychopharmacology

Volumn 232, Issue 6, 2015, Pages 1039-1047

  Fantegrossi, William E ^a   Gray, Bradley W ^a   Bailey, Jessica M ^b   Smith, Douglas A ^c   Hansen, Martin ^d,e   Kristensen, Jesper L ^d,e  

^a UNIVERSITY OF ARKANSAS FOR MEDICAL SCIENCES   (United States)

^b UNIVERSITY OF ARKANSAS FOR MEDICAL SCIENCES   (United States)

^c VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

^d UNIVERSITY OF COPENHAGEN   (Denmark)

^e UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

Drug abuse; Drug discrimination; Mouse; Serotonin receptor

Indexed keywords

2 [[2 (4 CYANO 2,5 DIMETHOXYPHENYL)ETHYLAMINO]METHYL]PHENOL; 4 IODO 2,5 DIMETHOXYAMPHETAMINE; 8 [5 [2,4 DIMETHOXY 5 (4 TRIFLUOROMETHYLPHENYLSULFONAMIDO)PHENYL] 5 OXOPENTYL] 1,3,8 TRIAZASPIRO[4.5]DECANE 2,4 DIONE; KETANSERIN; PHENETHYLAMINE DERIVATIVE; SEROTONIN 2A RECEPTOR; UNCLASSIFIED DRUG; VOLINANSERIN; 4-IODOAMPHETAMINE; AMPHETAMINE DERIVATIVE; FLUOROBENZENE; PHENETHYLAMINE; PIPERIDINE DERIVATIVE; PSYCHEDELIC AGENT; SEROTONIN 2 AGONIST; SEROTONIN 2 ANTAGONIST;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG ANTAGONISM; DRUG DISCRIMINATION TEST; DRUG SELECTIVITY; HALLUCINOGEN LIKE EFFECT; HEAD TWITCH; IN VIVO STUDY; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL; ANIMAL; DOSE RESPONSE; DRUG EFFECTS; HEAD MOVEMENT; METABOLISM;

AMPHETAMINES; ANIMALS; DOSE-RESPONSE RELATIONSHIP, DRUG; FLUOROBENZENES; HALLUCINOGENS; HEAD MOVEMENTS; KETANSERIN; MALE; MICE; PHENETHYLAMINES; PIPERIDINES; RECEPTOR, SEROTONIN, 5-HT2A; SEROTONIN 5-HT2 RECEPTOR AGONISTS; SEROTONIN 5-HT2 RECEPTOR ANTAGONISTS;

EID: 84923601036     PISSN: 00333158     EISSN: 14322072     Source Type: Journal    
DOI: 10.1007/s00213-014-3739-3     Document Type: Article

References (24)

1. Advisory Council on the Misuse of Drugs (ACMD) (2013) NBOMe, compounds: A review of the evidence of use and harm. Available at: https://www.gov.uk/government/uploads/system/uploads/attachment-data/file/20480 8/J-TCDO-report-on-5-6APB-and-NBOMe-compounds.pdf. Accessed 03 July 2014
2. Blaazer AR, Smid P, Kruse CG (2008) Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT(2A) receptors. Chem Med Chem 3(9):1299-1309
3. 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(6):1956-1964
4. Canal CE, Morgan D (2012) Head-twitch response in rodents induced by the hallucinogen 2,5-dimethoxy-4-iodoamphetamine: a comprehensive history, a re-evaluation of mechanisms, and its utility as a model. Drug Test Anal 4(7-8):556-576
5. Dekeyne A, Iob L, Hautefaye P and Millan MJ (2002) The selective serotonin(2A) receptor antagonist, MDL100,907, elicits a specific interoceptive cue in rats. Neuropsychopharmacology 26(4):552-6
6. Fantegrossi WE, Murnane KS, Reissig CJ (2008) The behavioral pharmacology of hallucinogens. Biochem Pharmacol 75(1):17-33
7. Fantegrossi WE, Simoneau J, Cohen MS, Zimmerman SM, Henson CM, Rice KC, Woods JH (2010) Interaction of 5-HT2A and 5-HT2C receptors in R(-)-2,5-dimethoxy-4-iodoamphetamine-elicited head twitch behavior in mice. J Pharmacol Exp Ther 335(3):728-734
8. Glennon RA, Raghupathi RK, Bartyzel P, Teitler M, Leonhardt S (1992) Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J Med Chem 35:734-740
9. Halberstadt AL, Geyer MA (2014) Effects of the hallucinogen 2,5-dimethoxy-4- iodophenethylamine (2C-I) and superpotent N-benzyl derivatives on the head twitch response. Neuropharmacol 77:200-207
10. Hansen M (2011) Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain. Ph.D. thesis, University of Copenhagen. Accessed at https://docs.google.com/file/d/0BwXelgjm5BeEaEJJU0lPa1NnaGM, 01 July 2014
11. Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, Kristensen JL (2014) Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists. ACS Chem Neurosci 5(3):243-249
12. Juncosa JI Jr, Hansen M, Bonner LA, Cueva JP, Maglathlin R, McCorvy JD, Marona-Lewicka D, Lill MA, Nichols DE (2013) Extensive rigid analogue design maps the binding conformation of potent N-benzylphenethylamine 5-HT2A serotonin receptor agonist ligands. ACS Chem Neurosci 4(1):96-109
13. Knight AR, Misra A, Quirk K, Benwell K, Revell D, Kennett G, Bickerdike M (2004) Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors. Naunyn Schmiedebergs Arch Pharmacol 370(2):114-123
14. Lawn W, Barratt M, Williams M, Horne A and Winstock A (2014) The NBOMe hallucinogenic drug series: Patterns of use, characteristics of users and self-reported effects in a large international sample. J Psychopharmacol, in press.
15. Leth-Petersen S, Bundgaard C, Hansen M, Carnerup MA, Kehler J and Kristensen JL (2014) Correlating the Metabolic Stability of Psychedelic 5-HT2A Agonists with Anecdotal Reports of Human Oral Bioavailability. Neurochem Res, in press.
16. Li JX, Unzeitig A, Javors MA, Rice KC, Koek W, France CP (2009) Discriminative stimulus effects of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM), ketanserin, and (R)-(+)-{alpha}-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-pipidinemethanol (MDL100907) in rats. J Pharmacol Exp Ther 331(2):671-679
17. McLean TH, Parrish JC, Braden MR, Marona-Lewicka D, Gallardo-Godoy A, Nichols DE (2006) 1-Aminomethylbenzocycloalkanes: conformationally restricted hallucinogenic phenethylamine analogues as functionally selective 5-HT2A receptor agonists. J Med Chem 49(19):5794-5803
18. Nichols DE (2004) Hallucinogens. Pharmacol Ther 101(2):131-181
19. Nichols DE, Frescas SP, Chemel BR, Rehder KS, Zhong D, Lewin AH (2008) High specific activity tritium-labeled N-(2-methoxybenzyl)-2,5-dimethoxy-4 -iodophenethylamine (INBMeO): a high-affinity 5-HT2A receptor-selective agonist radioligand. Bioorg Med Chem 16:6116-6123
20. Nikolaou P, Papoutsis I, Stefanidou M, Spiliopoulou C and Athanaselis S (2014) 2C-I-NBOMe, an N-bomb that kills with Smiles. Toxicological and legislative aspects. Drug Chem Toxicol, in press.
21. Parker MA, Marona-Lewicka D, Lucaites VL, Nelson DL, Nichols DE (1998) A novel (benzodifuranyl)aminoalkane with extremely potent activity at the 5-HT2A receptor. J Med Chem 41(26):5148-5149
22. Roth BL, Willins DL, Kristiansen K, Kroeze WK (1998) 5-Hydroxytryptamine2-family receptors (5-hydroxytryptamine2A, 5-hydroxytryptamine2B, 5-hydroxytryptamine2C): where structure meets function. Pharmacol Ther 79(3):231-257
23. Tang MH, Ching CK, Tsui MS, Chu FK, Mak TW (2014) Two cases of severe intoxication associated with analytically confirmed use of the novel psychoactive substances 25B-NBOMe and 25C-NBOMe. Clin Toxicol 52(5):561-565
24. Walterscheid JP, Phillips GT, Lopez AE, Gonsoulin ML, Chen HH, Sanchez LA (2014) Pathological findings in 2 cases of fatal 25I-NBOMe toxicity. Am J Forensic Med Pathol 35(1):20-25