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25B-NBOMe and its precursor 2C-B: modern trends and hidden dangers


Substituted phenethylamines are a class of designer drugs that hold a significant position in the drug abuse market. The most important substances within this class appear to be 4-bromo-2,5-dimethoxyphenethylamine (2C-B) and its novel derivative 2-(4-bromo-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethanamine (25B-NBOMe). Intoxications related to 2C-B use are still recorded worldwide, despite the fact that its use and trafficking are banned in many countries. 25B-NBOMe is a highly potent 2C-B derivative that has invaded recently in the “drug arena” and is considered legal to possess and supply in many countries. This manuscript reviews all available information regarding chemistry, availability, pharmacology, and toxicology of 2C-B and 25B-NBOMe. The intoxication and fatal cases reported, as well as the current legislation of these drugs, are also presented.

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  1. Nieddu M, Trignano C, Burrai L, Pirisi MA, Boatto G (2013) Cross-reactivities of 41 new amphetamine designer drugs to EMIT® immunoassays. Forensic Toxicol 31:133–137

    CAS  Article  Google Scholar 

  2. Advisory Council on the Misuse of Drugs (ACMD) (2013) “NBOMe” compounds: a review of the evidence of use and harm. Accessed 5 May 2014

  3. Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM (2013) 2C or not 2C: phenethylamine designer drug review. J Med Toxicol 9:172–178

    CAS  PubMed Central  PubMed  Article  Google Scholar 

  4. Stellpflug SJ, Kealey SE, Hegarty CB, Janis GC (2014) 2-(4-Iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine (25I-NBOMe): clinical case with unique confirmatory testing. J Med Toxicol 10:45–50

    CAS  PubMed  Article  Google Scholar 

  5. Wikipedia (2014) 2C (psychedelics). Accessed 8 May 2014

  6. Shulgin A, Shulgin A (1991) PiHKAL: a chemical love story. Transform Press, Berkeley

    Google Scholar 

  7. Bronson ME, Jiang W, DeRuiter J, Clark CR (1995) A behavioral comparison of Nexus, cathinone, BDB, and MDA. Pharmacol Biochem Behav 51:473–475

    CAS  PubMed  Article  Google Scholar 

  8. Shulgin AT, Carter MF (1975) Centrally active phenethylamines. Psychopharmacol Commun 1:93–98

    CAS  PubMed  Google Scholar 

  9. Lobos M, Borges Y, Gonzalez E, Cassels BK (1992) The action of the psychoactive drug 2C-B on isolated rat thoratic aorta. Gen Pharmacol 23:1139–1142

    CAS  PubMed  Article  Google Scholar 

  10. Huang HH, Bai YM (2011) Persistent psychosis after ingestion of a single tablet of “2C-B”. Prog Neuropsychopharmacol Biol Psychiatry 35:293–294

    PubMed  Article  Google Scholar 

  11. Ragan FA, Hite SA, Samuels MS, Garey RE (1985) 4-Bromo-2,5-dimethoxyphenethylamine: identification of a new street drug. J Anal Toxicol 9:91–93

    CAS  PubMed  Article  Google Scholar 

  12. Giroud C, Augsburger M, Rivier L, Mangin P, Sadephipour F, Varesio E, Veuthey JL, Kamalaprija P (1998) 2C-B: a new psychoactive phenethylamine recently discovered in ecstasy tablets sold on the Swiss black market. J Anal Toxicol 22:345–354

    CAS  PubMed  Article  Google Scholar 

  13. deBoer D, Gijzels MJ, Bosman IJ, Maes RA (1999) More data about the new psychoactive drug 2C-B. J Anal Toxicol 23:227–228

    CAS  Article  Google Scholar 

  14. Kanamori T, Nagasawa K, Kuwayama K, Tsujikawa K, Iwata YT, Inoue H (2013) Analysis of 4-bromo-2,5-dimethoxyphenethylamine abuser’s urine: identification and quantitation of urinary metabolites. J Forensic Sci 58:279–287

    CAS  PubMed  Article  Google Scholar 

  15. Heim R (2003) Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts (in German). Accessed 9 May 2014

  16. Blaazer AR, Smid P, Kruse CG (2008) Structure–activity relationships of phenylalkylamines as agonist ligands for 5-HT(2A) receptors. ChemMedChem 3:1299–1309

    CAS  PubMed  Article  Google Scholar 

  17. 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

    CAS  PubMed Central  PubMed  Article  Google Scholar 

  18. 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. Neuropharmacology 77:200–207

    CAS  PubMed  Article  Google Scholar 

  19. Tang MHY, Ching CK, Tsui MSH, Chu FKC, Mak TWL (2014) Two cases of severe intoxication associated with analytically confirmed use of the novel psychoactive substances 25B-NBOMe and 25C-NBOMe. Clin Toxicol 52:561–565

    CAS  Article  Google Scholar 

  20. Silva ME (2008) Theoretical study of the interaction of agonists with the 5-HT2A receptor. Accessed 8 May 2014

  21. Silva ME, Heim R, Strasser A, Elz S, Dove S (2011) Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor. J Comput Aided Mol Des 25:51–66

    CAS  PubMed  Article  Google Scholar 

  22. European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) (2012) New drugs in Europe. EMCDDA-Europol 2012 annual report on the implementation of council decision 2005/387/JHA. Accessed 10 May 2014

  23. Erowid (2005) 2C-B synthesis without LAH. Accessed 8 May 2014

  24. National Drug Intelligence Center (NDIC) (2001) Information bulletin 2C-B (Nexus) reappears on the club drug scene. Accessed 9 May 2014

  25. Cole MD, Lea C, Oxley N (2002) 4-Bromo-2,5-dimethoxyphenethylamine (2C-B): a review of the public domain literature. Sci Just 42:223–224

    CAS  Article  Google Scholar 

  26. Rohanova M, Palenicek T, Balikova M (2008) Disposition of 4-bromo-2,5-dimethoxyphenethylamine (2C-B) and its metabolite 4-bromo-2-hydroxy-5-methoxyphenethylamine in rats after subcutaneous administration. Toxicol Lett 178:29–36

    CAS  PubMed  Article  Google Scholar 

  27. Caudevilla-Galligo F, Riba J, Ventura M, Gonzalez D, Farre M, Barbanoj MJ, Bouso JC (2012) 4-Bromo-2,5-dimethoxyphenethylamine (2C-B): presence in the recreational drug market in Spain, pattern of use and subjective effects. J Psychopharmacol 26:1026–1035

    CAS  PubMed  Article  Google Scholar 

  28. Erowid (2014) 2C-B. Accessed 8 May 2014

  29. Wikipedia (2014) 2C-B. Accessed 8 May 2014

  30. Leicester City Council (2014) Drug data, contents of section 5, general information. Accessed 2 May 2014

  31. deBoer D, Bosman I (2004) A new trend in drugs-of-abuse; the 2C-series of phenethylamine designer drugs. Pharm World Sci 26:110–113

    CAS  Article  Google Scholar 

  32. King LA (2014) New phenethylamines in Europe. Drug Test Anal 6:808–818

    CAS  PubMed  Article  Google Scholar 

  33. MixMag (2012) Global drug survey. Accessed 9 May 2014

  34. Burns L, Roxburgh A, Matthews A, Bruno R, Lenton S, Van Buskirk J (2014) The rise of new psychoactive substance use in Australia. Drug Test Anal 6:846–849

    CAS  PubMed  Article  Google Scholar 

  35. Gine CV, Espinosa IF, Vilamala MV (2014) New psychoactive substances as adulterants of controlled drugs. A worrying phenomenon? Drug Test Anal 6:819–824

    CAS  PubMed  Article  Google Scholar 

  36. PsychonautWiki (2014) 2C-B. Accessed 10 May 2014

  37. Red Button Forum (2014) 2CB. Accessed 2 May 2014

  38. Cayman Chemical (2014) Item number 12047, 25B-NBOMe (hydrochloride).;jsessionid=24B0B4AEB5BAD0573691AEFFF54C2622. Accessed 6 May 2014

  39. Moya PR, Berg KA, Gutierrez-Hernandez MA, Saez-Briones P, Reyes-Parada M, Cassels BK, Clarke WP (2007) Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors. J Pharmacol Exp Ther 321:1054–1061

    CAS  PubMed  Article  Google Scholar 

  40. Kanamori T, Inoue H, Iwata Y, Ohmae Y, Kishi T (2002) In vivo metabolism of 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in the rat: identification of urinary metabolites. J Anal Toxicol 26:61–66

    CAS  PubMed  Article  Google Scholar 

  41. Carmo H, deBoer D, Remiao F, Carvalho F, dos Reys LA, Bastos ML (2004) Metabolism of the designer drug 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in mice, after acute administration. J Chromatogr B 811:143–152

    CAS  Article  Google Scholar 

  42. Carmo H, Hengstler JG, deBoer D, Ringel M, Remiao F, Carvalho F, Fernandes E, dos Reys LA, Oesch F, Bastos ML (2005) Metabolic pathways of 4-bromo-2,5-dimethoxyphenethylamine (2C-B): analysis of phase I metabolism with hepatocytes of six species including human. Toxicology 206:75–89

    CAS  PubMed  Article  Google Scholar 

  43. Kanamori T, Tsujikawa K, Ohmae Y, Iwata YT, Inoue H, Kishi T, Nakahama T, Inouye Y (2005) A study of the metabolism of methamphetamine and 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in isolated rat hepatocytes. Forensic Sci Int 148:131–137

    CAS  PubMed  Article  Google Scholar 

  44. Theobald DS, Fritschi G, Maurer HH (2007) Studies on the toxicological detection of the designer drug 4-bromo-2,5-dimethoxy-β-phenethylamine (2C-B) in rat urine using gas chromatography-mass spectrometry. J Chromatogr B 846:374–377

    CAS  Article  Google Scholar 

  45. Palenicek T, Fujakova M, Brunovsky M, Horacek J, Gorman I, Balikova M, Rambousek L, Syslova K, Kacer P, Zach P, Bubenikova-Valesova V, Tyls F, Kubesova A, Puskarcikova J, Hoschl C (2013) Behavioral, neurochemical and pharmaco-EEG profiles of the psychedelic drug 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in rats. Psychopharmacology 225:75–93

    CAS  PubMed  Article  Google Scholar 

  46. Talk to Frank Forum (2013) 2CB: random letters and numbers or something more serious? Accessed 9 May 2014

  47. Disregard Everything I Say (DEIS) (2013) 2C-B, broken down and described. Accessed 14 May 2014

  48. Youth Rise Forum (2014) Phenethylamines (2CX, DOX, 25IX, etc.). Accessed 5 May 2014

  49. Ambrose JB, Bennet BA, Lee HS, Josephson SA (2010) Cerebral vasculopathy after 4-bromo-2,5-dimethoxyphenethylamine ingestion. Neurologist 16:199–202

    PubMed  Article  Google Scholar 

  50. Namera A, Yashiki M, Kojima T, Ueki M (2002) Automated headspace solid-phase microextraction and in-matrix derivatization for the determination of amphetamine-related drugs in human urine by gas chromatography–mass spectrometry. J Chromatogr Sci 40:19–25

    CAS  PubMed  Article  Google Scholar 

  51. Soares ME, Carvalho M, Carmo H, Remiao F, Carvalho F, Bastos ML (2004) Simultaneous determination of amphetamine derivatives in human urine after SPE extraction and HPLC-UV analysis. Biomed Chromatogr 18:125–131

    CAS  PubMed  Article  Google Scholar 

  52. Kim JY, Jung KS, Kim MK, Lee JII, In MK (2007) Simultaneous determination of psychotropic phenylalkylamine derivatives in human hair by gas chromatography/mass spectrometry. Rapid Commun Mass Spectrom 21:1705–1720

    CAS  PubMed  Article  Google Scholar 

  53. Kerrigan S, Mott A, Jatzlau B, Ortiz F, Perrella L, Martin S, Bryand K (2014) Designer psychostimulants in urine by liquid chromatography-tandem mass spectrometry. J Forensic Sci 59:175–183

    CAS  PubMed  Article  Google Scholar 

  54. World Health Organization (WHO) (2001) WHO expert committee on drug dependence. Thirty second report. Accessed 8 May 2014

  55. Casale JF, Hays PA (2012) Characterization of eleven 2,5-dimethoxy-N-(2-methoxybenzyl)phenethylamine (NBOMe) derivatives and differentiation from their 3- and 4-methoxybenzyl analogues–Part I. Microgram J 9:84–109

    CAS  Google Scholar 

  56. United Nations Office on Drugs and Crime (UNODC) (2013) Global smart update. Accessed 9 May 2014

  57. European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) (2014) European database on new drugs (EDND), phenethylamines, 25B-NBOMe. Accessed 6 May 2014

  58. Wikipedia (2014) 25B-NBOMe. Accessed 9 May 2014

  59. Drug Enforcement Administration (DEA) (2013) 25I-NBOMe, 25C-NBOMe, and 25B-NBOMe (street names: N-bomb, Smiles, 25I, 25C, 25B). Accessed on 6 May 2014

  60. Erowid (2012) 2C-B-NBOMe reports (also 25B-NBOMe). Accessed 3 May 2014

  61. Uchiyama N, Shimokawa Y, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (2014) Two new synthetic cannabinoids, AM-2201 benzimidazole analog (FUBIMINA) and (4-methylpiperazin-1-yl)(1-pentyl-1H-indol-3-yl)methanone (MEPIRAPIM), and three phenethylamine derivatives, 25H-NBOMe 3,4,5-trimethoxybenzyl analog, 25B-NBOMe, and 2C-N-NBOMe, identified in illegal products. Forensic Toxicol 32:105–115

    CAS  Article  Google Scholar 

  62. Lawn W, Barratt M, Williams M, Horne A, 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 28:780–788

    CAS  PubMed  Article  Google Scholar 

  63. Drugs Forum (2014) 25B-NBOMe. Accessed 9 May 2014

  64. PsychonautWiki (2014) 25B-NBOMe. Accessed 10 May 2014

  65. Ettrup A, Holm S, Hansen M, Wasim M, Santini MA, Palner M, Madsen J, Svarer C, Kristensen JL, Knudsen GM (2013) Preclinical safety assessment of the 5-HT2A receptor agonist PET radioligand [11C]Cimbi-36. Mol Imag Biol 15:376–383

    Article  Google Scholar 

  66. Poklis JL, Charles J, Wolf CE, Poklis A (2013) High-performance liquid chromatography tandem mass spectrometry method for the determination of 2CC-NBOMe and 25I-NBOMe in human serum. Biomed Chromatogr 27:1794–1800

    CAS  PubMed Central  PubMed  Article  Google Scholar 

  67. Disregard Everything I Say (DEIS) (2014) 25B-NBOMe, broken down and described. Accessed 14 May 2014

  68. Shroomery Forum (2012) New hallucinogenic drug 25B-NBOMe and 25I-NBOMe led to South Australian man’s bizarre death. Accessed 9 May 2014

  69. Rice S (2012) New hallucinogenic drug 25B-NBOMe and 25I-NBOMe led to South Australian man’s bizarre death. Accessed 8 May 2014

  70. Poklis JL, Nanco CR, Troendle MM, Wolf CE, Poklis A (2014) Determination of 4-bromo-2,5-dimethoxy-N-[(2-methoxyphenyl)methyl]-benzeneethanamine (25B-NBOMe) serum and urine by high performance liquid chromatography with tandem mass spectrometry in a case of severe intoxication. Drug Test Anal 6:764–769

    CAS  PubMed Central  PubMed  Article  Google Scholar 

  71. Sporkert F, Augsburger M, Vilarino R, Michaud K, Schlapfer M, Marcourt L (2013) Identification and implication of the phenethylamine derivative 25B-NBOMe in a case of an unresolved fatality. The 51st annual meeting of the International Association of Forensic Toxicologists, Madeira

  72. Neurosoup Forum (2013) 25B-NBOMe (2C-B-NBOMe) hospitalization. Accessed 8 May 2014

  73. Erowid (2012) 25I-NBOMe. Accessed 3 May 2014

  74. Scientific Working Group for the Analysis of Seized Drugs (SWGDRUG) (2013) 25B-NBOMe. Accessed 9 May 2014

  75. Forendex Forum (2014) Southern Association of Forensic Scientists. Accessed 5 May 2014

  76. Home Office (2013) ‘NBOMe’ and ‘Benzofury’ banned. Accessed 14 May 2014

  77. Drug Enforcement Administration (DEA), Department of Justice (2013) Schedules of controlled substances: temporary placement of three synthetic phenethylamines into Schedule I. Final Order. Fed Reg 78:68716–68719

    Google Scholar 

  78. Läkemedelsverkets författningssamling (2013) Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika (in Swedish). Accessed 8 May 2014

  79. Sundhedsstyrelsen (2013) Health and treatment/narcotico (in Danish). file:///C:/Users/user/Downloads/DK_NBOMe%20substances%20risk%20assessment%20(3).pdf. Accessed 8 May 2014

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Correspondence to Panagiota Nikolaou.

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Papoutsis, I., Nikolaou, P., Stefanidou, M. et al. 25B-NBOMe and its precursor 2C-B: modern trends and hidden dangers. Forensic Toxicol 33, 1–11 (2015).

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  • 2C-B
  • Nexus
  • 25B-NBOMe
  • New Nexus
  • Substituted phenethylamines
  • Toxicology and pharmacology