NBOMe: New potent hallucinogens-pharmacology, analytical methods, toxicities, fatalities: A review

European Review for Medical and Pharmacological Sciences

Volumn 19, Issue 17, 2015, Pages 3270-3281

  Kyriakou, C ^a   Marinelli, E ^a   Frati, P ^a   Santurro, A ^a   Afxentiou, M ^b   Zaami, S ^a   Busardo, Francesco Paolo ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b State General Laboratory   (Cyprus)

Author keywords

Analytical methods; Fatalities; Intoxication; N Bomb; NBOMe; Pharmacology

Indexed keywords

PSYCHEDELIC AGENT; SEROTONIN 2A RECEPTOR; 2-(4-CHLORO-2,5-DIMETHOXYPHENYL)-N-((2-METHOXYPHENYL)METHYL)ETHANAMINE; BENZYLAMINE DERIVATIVE; PHENETHYLAMINE DERIVATIVE;

ANALYTIC METHOD; DISEASE SEVERITY; DRUG DETERMINATION; DRUG FATALITY; DRUG INTOXICATION; DRUG POTENCY; HUMAN; PUBLIC HEALTH PROBLEM; REVIEW; STRUCTURE ACTIVITY RELATION; SYSTEMATIC REVIEW; ADDICTION; COMPLICATION; DRUG OVERDOSE;

BENZYLAMINES; DRUG OVERDOSE; HALLUCINOGENS; HUMANS; PHENETHYLAMINES; SUBSTANCE-RELATED DISORDERS;

EID: 84960325099     PISSN: 11283602     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (47)

1. KING LA, KICMAN AT. A brief history of 'new psychoactive substances'. Drug Test Anal 2011; 3: 401-403.
2. JOHNSON LA, JOHNSON RL, PORTIER RB. Current "legal highs". J Emerg Med 2013; 44: 1108-1115.
3. WEAVER MF, HOPPER JA, GUNDERSON EW. Designer drugs 2015: Assessment and management. Addict Sci Clin Pract 2015; 10: 8.
4. BRADEN MR, PARRISH JC, NAYLOR JC, NICHOLS DE. Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists. Mol Pharm 2006; 70: 1956-1964.
5. NIKOLAOU P, PAPOUTSIS I, STEFANIDOU M, SPILIOPOULOU C, ATHANASELIS S. 2C-I-NBOMe, an "N-bomb" that kills with "Smiles". Toxicological and legislative aspects. Drug Chem Toxicol 2015; 38: 113-119.
6. DEAN BV, STELLPFLUG SJ, BURNETT AM, ENGEBRETSEN KM. 2C or not 2C: Phenethylamine designer drug review. J Med Toxicol 2013; 9: 172-178.
7. LINDIGKEIT R, BOEHME A, EISERLOH I, LUEBBECKE M, WIGGERMANN M, ERNST L, BEUERLE T. Spice: A never ending story? Forensic Sci Int 2009; 191: 58-63.
8. ZUBA D, SEKULA K, BUCZEK A. 25C-NBOMe-new potent hallucinogenic substance identified on the drug market. Forensic Sci Int 2013; 227: 7-14.
9. ZUBA D, SEKULA K. Analytical characterization of three hallucinogenic N-(2-methoxy)benzyl derivatives of the 2C-series of phenethylamine drugs. Drug Test Anal 2013; 5: 634-645.
10. HALBERSTADT AL, GEYER MA. Effects of the hallucinogen 2,5-dimethoxy-4-iodophenethylamine (2C-I) and superpotent N-benzyl derivatives on the head twitch response. Neuropharmacology 2014; 77: 200-207.
11. SUZUKI J, POKLIS JL, POKLIS A. "My friend said it was good LSD": A suicide attempt following analytically confirmed 25I-NBOMe ingestion. J Psychoactive Drugs 2014; 46: 379-382.
12. NINNEMANN A, STUART GL. The NBOMe series: A novel, dangerous group of hallucinogenic drugs. J Stud Alcohol Drugs 2013; 74: 977-978.
13. FORRESTER MB. NBOMe designer drug exposures reported to Texas poison centers. J Addict Dis 2014; 33: 196-201.
14. LAWN W, BARRATT M, WILLIAMS M, HORNE A, WINSTOCK A. The NBOMe hallucinogenic drug series: Patterns of use, characteristics of users and self-reported effects in a large international sample. J Psychopharmacol 2014; 28: 780-788.
15. ETTRUP A, HANSEN M, SANTINI MA, PAINE J, GILLINGS N, PALNER M, LEHEL S, HERTH MM, MADSEN J, KRISTENSEN J, BEGTRUP ME, KNUDSEN GM. Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT (2A) agonist PET tracers. Eur J Nucl Med Mol Imaging 2011; 38: 681-693.
16. HANSEN M, PHONEKEO K, PAINE JS, LETH-PETERSEN S, BEGTRUP M, BRAUNER-OSBORNE H, KRISTENSEN JL. Synthesis and structure-activity relationships of Nbenzyl phenethylamines as 5-HT2A/2C agonists. ACS Chem Neurosci 2014; 5: 243-249.
17. GONZÁLEZ-MAESO J, WEISSTAUB NV, ZHOU M, CHAN P, IVIC L, ANG R, LIRA A, BRADLEY-MOORE M, GE Y, ZHOU Q, SEALFON SC, GINGRICH JA. Hallucinogens recruit specific cortical 5-HT(2A) receptor-mediated signaling pathways to affect behavior. Neuron 2007; 53: 439-452.
18. GLENNON RA, RAGHUPATHI R, BARTYZEL P, TEITLER M, LEONHARDT S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: Evidence for a lack of selectivity. J Med Chem 1992; 35: 734-740.
19. HELLER WA, BARABAN JM. Potent agonist activity of DOB at 5-HT2 receptors in guinea pig trachea. Eur J Pharmacol 1987; 138: 115-117.
20. SANDERS-BUSH E, BURRIS KD, KNOTH K. Lysergic acid diethylamide and 2,5-dimethoxy-4-methylamphetamine are partial agonists at serotonin receptors linked to phosphoinositide hydrolysis. J Pharmacol Exp Ther 1988; 246: 924-928.
21. SEGGEL MR, YOUSIF MY, LYON RA, TITELER M, ROTH BL, SUBA EA, GLENNON RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5- dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J Med Chem 1990; 33: 1032-1036.
22. KIER LB, GLENNON RA. Progress with several models for the study of the SAR of hallucinogenic agents. NIDA Res Monogr 1978: 159-185.
23. KLOPMAN G, MACINA OT. Use of the Computer Automated Structure Evaluation program in determining quantitative structure-activity relationships within hallucinogenic phenylalkylamines. J Theor Biol 1985; 113: 637-648.
24. THAKUR M, THAKUR A, KHADIKAR PV. QSAR studies on psychotomimetic phenylalkylamines. Bioorgan Med Chem 2004; 12: 825-831.
25. NEUVONEN K, NEUVONEN H, FULOP F. Effect of 4- substitution on psychotomimetic activity of 2,5- dimethoxy amphetamines as studied by means of different substituent parameter scales. Bioorg Med Chem Lett 2006; 16: 3495-3498.
26. BRADEN MR. Towards a biophysical understanding of hallucinogens action, Purdue University, West Lafayette, IN, USA, 2006 (Ph.D. Thesis).
27. SILVA ME, HEIM R, STRASSER A, ELZ S, DOVE S. Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor. J Comput Aided Mol Des 2011; 25: 51-66.
28. HEIM R. Synthesis and pharmacology of potent 5- HT2A receptor agonists withN-2-Methoxybenzyl partial structure, Free University, Berlin, Germany, 2003 (Ph.D. Thesis).
29. STELLPFLUG SJ, KEALEY SE, HEGARTY CB, JANIS GC. 2- ( 4 - I o d o - 2 , 5 - d ime t h o x y p h e n y l ) - N - [ ( 2 - methoxyphenyl)methyl]ethanamine (25I-NBOMe): Clinical case with unique confirmatory testing. J Med Toxicol 2014; 10: 45-50.
30. POKLIS JL, CHARLES J, WOLF CE, POKLIS A. High-performance liquid chromatography tandem mass spectrometry method for the determination of 2CC-NBOMe and 25I-NBOMe in human serum. Biomed Chromatogr 2013; 27: 1794-1800.
31. POKLIS JL, CLAY DJ, POKLIS A. High-performance liquid chromatography with tandem mass spectrometry for the determination of nine hallucinogenic 25-NBOMe designer drugs in urine specimens. J Anal Toxicol 2014; 38: 113-121.
32. POKLIS JL, NANCO CR, TROENDLE MM, WOLF CE, POKLIS A. Determination of 4-bromo-2,5-dimethoxy-N- [(2-methoxyphenyl)methyl]-benzeneethanamine (25B-NBOMe) in serum and urine by high performance liquid chromatography with tandem mass spectrometry in a case of severe intoxication. Drug Test Anal 2014; 6: 764-769.
33. ANDREASEN MF, TELVING R, ROSENDAL I, EG MB, HASSELSTROM JB, ANDERSEN LV. A fatal poisoning involving 25C-NBOMe. Forensic Sci Int 2015; 251: E1- 8.
34. PASIN D, BIDNY S, FU S. Analysis of new designer drugs in post-mortem blood using high-resolution mass spectrometry. J Anal Toxicol. 2015; 39: 163-171.
35. ARMENIAN P, GERONA RR. The electric Kool-Aid NBOMe test: LC-TOF/MS confirmed 2C-CNBOMe (25C) intoxication at Burning Man. Am J Emerg Med 2014; 32: 1444 e3-5.
36. COELHO NETO J. Rapid detection of NBOME's and other NPS on blotter papers by direct ATRFTIR spectrometry. Forensic Sci Int 2015; 252: 87-92.
37. CALDICOTT DG, BRIGHT SJ, BARRATT MJ. NBOMe - A very different kettle of fish. Med J Aust 2013; 199: 322-323.
38. SUZUKI J, DEKKER MA, VALENTI ES, ARBELO CRUZ FA, CORREA AM, POKLIS JL, POKLIS A. Toxicities associated with NBOMe ingestion-A novel class of potent hallucinogens: A review of the literature. Psychosomatics 2015; 56: 129-139.
39. HILL SL, DORIS T, GURUNG S, KATEBE S, LOMAS A, DUNN M, BLAIN P, THOMAS SH. Severe clinical toxicity associated with analytically confirmed recreational use of 25I-NBOMe: Case series. Clin Toxicol (Phila) 2013; 51: 487-492.
40. ROSE SR, POKLIS JL, POKLIS A. A case of 25I-NBOMe (25-I) intoxication: A new potent 5-HT2A agonist designer drug. Clin Toxicol (Phila) 2013; 51: 174-177.
41. GRAUTOFF S, KAHLER J. Near fatal intoxication with the novel psychoactive substance 25C-NBOMe. Med Klin Intensivmed Notfmed 2014; 109: 271-275.
42. TANG MH, CHING CK, TSUI MS, CHU FK, MAK TW. Two cases of severe intoxication associated with analytically confirmed use of the novel psychoactive substances 25B-NBOMe and 25C-NBOMe. Clin Toxicol (Phila) 2014; 52: 561-565.
43. KELLY A, EISENGA B, RILEY B, JUDGE B. Case series of 25I- NBOMe exposures with laboratory confirmation. Available at: Http: //www.clintox.org/NACCT/2012/NACCT-Post er-Abstracts-2012.pdf. (accessed June 1, 2015).
44. POKLIS JL, DEVERS KG, ARBEFEVILLE EF, PEARSON JM, HOUSTON E, POKLIS A. Postmortem detection of 25INBOMe [2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2- methoxyphenyl)methyl]ethanamine] in fluids and tissues determined by high performance liquid chromatography with tandem mass spectrometry from a traumatic death. Forensic Sci Int 2014; 234: E14-20.
45. KUEPPERS VB, COOKE CT. 25I-NBOMe related death in Australia: A case report. Forensic Sci Int 2015; 249: E15-18.
46. WALTERSCHEID JP, PHILLIPS GT, LOPEZ AE, GONSOULIN ML, CHEN HH, SANCHEZ LA. Pathological findings in 2 cases of fatal 25I-NBOMe toxicity. Am J Forensic Med Pathol 2014; 35: 20-25.
47. PASSIE T, HALPERN JH, STICHTENOTH DO, EMRICH HM, HINTZEN A. The pharmacology of lysergic acid diethylamide: A review. CNS Neurosci Ther 2008; 14: 295-314.