4-Bromo-2,5-dimethoxyphenethylamine (2C-B): Presence in the recreational drug market in Spain, pattern of use and subjective effects

Journal of Psychopharmacology

Volumn 26, Issue 7, 2012, Pages 1026-1035

  Caudevilla Gálligo, Fernando ^a,b   Riba, Jordi ^c,d,e,f   Ventura, Mireia ^g   González, Débora ^e,h   Farré, Magí ^e,h   Barbanoj, Manel J ^d,e,f   Bouso, José Carlos ^c,d,e,f  

^a Centro de Salud Puerta Bonita i   (Spain)

^b Grupo de Intervencion en Drogas de la Sociedad Espanola de Medicina Familiar y Comunitaria   (Spain)

^c Human Experimental Neuropsychopharmacology   (Spain)

^d HOSPITAL DE LA SANTA CREU I SANT PAU   (Spain)

^e UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^f CENTRO DE INVESTIGACIÓN BIOMÉDICA EN RED DE SALUD MENTAL CIBERSAM   (Spain)

^g Asociacion Bienestar y Desarrollo   (Spain)

^h HOSPITAL DEL MAR   (Spain)

Author keywords

2C B; club drugs; designer drugs; pattern of use; subjective effects

Indexed keywords

3,4 METHYLENEDIOXYMETHAMPHETAMINE; 4 BROMO 2,5 DIMETHOXYPHENETHYLAMINE; AMPHETAMINE; COCAINE; DEXAMPHETAMINE; KETAMINE; MESCALINE; PHENETHYLAMINE DERIVATIVE; PSYCHEDELIC AGENT; RECREATIONAL DRUG; UNCLASSIFIED DRUG;

ADULT; ARTICLE; BLOOD SAMPLING; CLINICAL ARTICLE; DRUG ABUSE PATTERN; DRUG DEPENDENCE; FEMALE; GAS CHROMATOGRAPHY; HUMAN; MALE; MASS SPECTROMETRY; PLEASURE; POWDER; PRIORITY JOURNAL; SALVIA; SALVIA DIVINORUM; SELF REPORT; SOCIAL BEHAVIOR; SPAIN; TABLET FORMULATION; THIN LAYER CHROMATOGRAPHY; ULTRAVIOLET SPECTROPHOTOMETRY;

ADULT; DANGEROUS BEHAVIOR; DESIGNER DRUGS; DIMETHOXYPHENYLETHYLAMINE; DRUG-SEEKING BEHAVIOR; FEMALE; HALLUCINOGENS; HUMANS; MALE; MIDDLE AGED; PERCEPTUAL DISTORTION; PREVALENCE; PSYCHOTROPIC DRUGS; RETROSPECTIVE STUDIES; SELF REPORT; SPAIN; SUBSTANCE-RELATED DISORDERS; TABLETS; YOUNG ADULT;

EID: 84862907041     PISSN: 02698811     EISSN: 14617285     Source Type: Journal    
DOI: 10.1177/0269881111431752     Document Type: Article

References (65)

1. Abanades S, Farré M, Barral D, Torrens M, Closas N, Langohr K, et al. Relative abuse liability of gamma-hydroxybutyric acid, flunitrazepam, and ethanol in club drug users. J Clin Psychopharmacol. 2007; 27: 625-638 (Pubitemid 351339451)
2. Ambrose JB, Bennett HD, Lee HS, Josephson SA. Cerebral vasculopathy after 4-bromo-2,5-dimethoxyphenethylamine ingestion. Neurologist. 2010; 16: 199-202
3. Andreasen MF, Telving R, Birkler RI, Schumacher B, Johannsen M. A fatal poisoning involving Bromo-Dragonfly. Forensic Sci Int. 2009; 183: 91-96
4. Baggott MJ, Coyle JR, Erowid E, Erowid F, Robertson LC. Abnormal visual experiences in individuals with histories of hallucinogen use: A web-based questionnaire. Drug Alcohol Depend. 2011; 114: 61-67
5. Barbanoj MJ, Riba J, Clos S, Giménez S, Grasa E, Romero S. Daytime Ayahuasca administration modulates REM and slow-wave sleep in healthy volunteers. Psychopharmacology (Berl). 2008; 196: 315-326
6. Bell SE, Burns DT, Dennis AC, Speers JS. Rapid analysis of ecstasy and related phenethylamines in seized tablets by Raman spectroscopy. Analyst. 2000; 125: 541-544 (Pubitemid 30179332)
7. Bouso JC Qué son las drogas de síntesis?. Madrid: RBA Integral; 2003 :
8. Bouso JC, Doblin R, Farré M, Alcázar MA, Gómez-Jarabo G. MDMAassisted psychotherapy using low doses in a small sample of women with chronic posttraumatic stress disorder. J Psychoactive Drugs. 2008; 40: 225-236
9. Capdevila M MDMA o el éxtasis químico. Barcelona: Los libros de la Liebre de marzo; 1995 :
10. CarabañaC (2009) Crisis en el éxtasis. Madrid: El País. Available at: http://www.elpais.com/articulo/sociedad/Crisis/ extasis/elpepusoc/20090711elpepusoc-1/Tes (accessed on 1 December 2010).
11. Carmo H, Brulport M, Hermes M, Oesch F, de Boer D, Remião F, et al. CYP2D6 increases toxicity of the designer drug 4-methylthioamphetamine (4-MTA). Toxicology. 2007; 229: 236-244 (Pubitemid 44937495)
12. Carmo H, Hengstler JG, de Boer D, Ringel M, Remião F, Carvalho F, et al. Metabolic pathways of 4-bromo-2,5-dimethoxyphenethylamine (2C-B): analysis of phase I metabolism with hepatocytes of six species including human. Toxicology. 2005; 206: 75-89 (Pubitemid 39610478)
13. Curtis B, Kemp P, Harty L, Choi C, Christensen D. Postmortem identification and quantitation of 2,5-dimethoxy-4-n-propylthiophenethylamine using GC-MSD and GC-NPD. J Anal Toxicol. 2003; 27: 493-498 (Pubitemid 37185861)
14. de Boer D, Bosman I. A new trend in drugs-of-abuse; the 2C-series of phenethylamine designer drugs. Pharm World Sci. 2004; 26: 110-113 (Pubitemid 38418600)
15. de la Torre R, Farré M, Roset PN, Lopez CH, Mas M, Ortuño J, et al. Pharmacology of MDMA in humans. Ann N Y Acad Sci. 2000; 914: 225-37
16. Drug Enforcement Administration (2003) DEA announces arrests of website operators selling illegal designer drugs Drug Enforcement Administration. Washington. Available at: http://www.justice.gov/dea/pubs/pressrel/pr072204.html (accessed on 8 April 2010).
17. Erowid (2009) 2C-B Vault: Legal Status. The Vaults of Erowid (version 3/11/2009). Available at: http://www.erowid.org/chemicals/2cb/2cb-law.shtml (accessed on 8 April 2010).
18. Escohotado A. 2CB. Revista Cáñamo. Especial Sexo y Drogas. 2003;: 45-47
19. European Monitoring Center for Drugs and Drug Addiction (2003) Early Warning System. Available at: http://www.emcdda.europa.eu/themes/new-drugs/ early-warning (accessed on 1 December 2010).
20. European Monitoring Center for Drug and Drug Addiction (2009a) Annual report on the state of the drugs problem in Europe. Lisbon. Available at: http://www.emcdda.europa.eu/publications/annual-report/2009 (accessed 12 December 2010).
21. European Monitoring Center for Drug and Drug Addiction (2009b) Record number of new drugs in Europe. Available at: http://www.emcdda.europa.eu/ publications/drugnet/online/2010/70/article1 (accessed 12 December 2010).
22. Gamella JF, Alvarez Roldán A Las rutas del éxtasis. Drogas de síntesis y las nuevas culturas juveniles. Barcelona: Ariel; 1999 :
23. Giroud C, Augsburger M, Rivier L, Mangin P, Sadeghipour F, Varesio E, et al. 2C-B: a new psychoactive phenylethylamine recently discovered in Ecstasy tablets sold on the Swiss black market. J Anal Toxicol. 1998; 22: 345-354 (Pubitemid 28397529)
24. González D, Riba J, Bouso JC, Gómez-Jarabo G, Barbanoj MJ. Pattern of use and subjective effects of Salvia divinorum among recreational users. Drug Alcohol Depend. 2006; 85: 157-162 (Pubitemid 44468138)
25. Gouzoulis-Mayfrank E, Thelen B, Habermeyer E, Kunert HJ, Kovar KA, Lindenblatt H, et al. Psychopathological, neuroendocrine and autonomic effects of 3,4-methylenedioxyethylamphetamine (MDE), psilocybin and d-methamphetamine in healthy volunteers. Results of an experimental double-blind placebo-controlled study. Psychopharmacology (Berl). 1999; 142: 41-50 (Pubitemid 29196062)
26. Greer G, Tolbert R. Subjective reports of the effects of MDMA in a clinical setting. J Psychoactive Drugs. 1986; 18: 319-327 (Pubitemid 17231263)
27. Griffith JD, Nutt JG, Jasinski DR. A comparison of fenfluramine and amphetamine in man. Clin Pharmacol Ther. 1975; 18: 563-570
28. Grob CS, Poland RE, Chang L, Ernst T. Psychobiologic effects of 3,4-methylenedioxymethamphetamine in humans: methodological considerations and preliminary observations. Behav Brain Res. 1996; 73: 103-107 (Pubitemid 26008769)
29. Halpern JH, Pope HG. Hallucinogen persisting perception disorder: what do we know after 50 years?. Drug Alcohol Depend. 2003; 69: 109-119 (Pubitemid 36259773)
30. Hernández-López C, Farré M, Roset PN, Menoyo E, Pizarro N, Ortuño J, et al. 3,4-Methylenedioxymethamphetamine (MDMA, Ecstasy) and alcohol interactions in humans: Psychomotor performance, subjective effects and pharmacokinetics. J Pharmacol Exp Ther. 2002; 300: 236-244 (Pubitemid 34028533)
31. Hidalgo E ¿Sabes lo que te metes? Pureza y adulteración de drogas en España. Madrid: Amargord; 2007 :
32. Holland J Ecstasy: the complete guide. A comprehensive look at the risks and benefits of MDMA. Holland J, ed. Rochester, Vermont: Park Street Press; 2001 :
33. Huang HH, Bai YM. Persistent psychosis after ingestion of a single tablet of '2C-B'. Prog Neuropsychopharmacol Biol Psychiatry. 2011; 35: 293-294
34. International Narcotics Control Board (2003) List of psychotropic substances under international control. 23rd Edition. Vienna: INCB. Available at: http://www.incb.org/pdf/e/list/green.pdf (accessed on 1 December 2010).
35. Johansen SS, Hansen AC, Müller IB, Lundemose JB, Franzmann MB. Three fatal cases of PMA and PMMA poisoning in Denmark. J Anal Toxicol. 2003; 27: 253-256 (Pubitemid 36666836)
36. Kanamori T, Tsujikawa K, Ohmae Y, Iwata YT, Inoue H, Kishi T, et al. A study of the metabolism of methamphetamine and 4-bromo-2,5- dimethoxyphenethylamine (2C-B) in isolated rat hepatocytes. Forensic Sci Int. 2005; 148: 131-137 (Pubitemid 40082402)
37. Krupitsky E, Burakov A, Romanova T, Dunaevsky I, Strassman R, Grinenko A. Ketamine psychotherapy for heroin addiction: immediate effects and two-year follow-up. J Subst Abuse Treat. 2002; 23: 273-283 (Pubitemid 35477807)
38. Liester MB, Grob CS, Bravo GL, Walsh RN. Phenomenology and sequelae of 3,4-methylenedioxymethamphetamine use. J Nerv Ment Dis. 1992; 180: 345-352
39. McLean TH, Parrish JC, Braden MR, Marona-Lewicka D, Gallardo-Godoy A, Nichols DE. 1-Aminomethylbenzocycloalkanes: conformationally restricted hallucinogenic phenethylamine analogues as functionally selective 5-HT2A receptor agonists. J Med Chem. 2006; 49: 5794-5803 (Pubitemid 44423716)
40. Montgomery T, Buon C, Eibauer S, Guiry PJ, Keenan AK, McBean GJ. 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. 2007; 152: 1121-1130 (Pubitemid 350166048)
41. Ott J Pharmacotheon. Entheogenic drugs, their plant sources and history. Kennewick, WA: The Natural Products Co; 1993 :
42. Pichini S, Pujadas M, Marchei E, Pellegrini M, Fiz J, Pacifici R, et al. Liquid chromatography-atmospheric pressure ionization electrospray mass spectrometry determination of "hallucinogenic designer drugs" in urine of consumers. J Pharm Biomed Anal. 2008; 47: 335-342
43. Poudevida S, Farré M, Roset PN, Camí J. Construcción de un cuestionario para la Valoración de los Efectos Subjetivos de Sustancias con Potencial de Abuso (VESSPA): Evaluación del éxtasis. Adicciones. 2003; 15: 19-30
44. Psychonaut Web Mapping Project (2010) Available at: http://194.83.136. 209/index.php (accessed on 1 December 2010).
45. Riba J, Rodriguez-Fornells A, Strassman RJ, Barbanoj MJ. Psychometric assessment of the Hallucinogen Rating Scale. Drug Alcohol Depend. 2001a; 62: 215-223 (Pubitemid 32276069)
46. Riba J, Rodriguez-Fornells A, Urbano G, Morte A, Antonijoan R, Montero M, et al. Subjective effects and tolerability of the South American psychoactive beverage Ayahuasca in healthy volunteers. Psychopharmacology (Berl). 2001b; 154: 85-95 (Pubitemid 32186519)
47. Riba J, Valle M, Urbano G, Yritia M, Morte A, Barbanoj MJ. Human pharmacology of ayahuasca: subjective and cardiovascular effects, monoamine metabolite excretion, and pharmacokinetics. J Pharmacol Exp Ther. 2003; 306: 73-83 (Pubitemid 36734359)
48. Riba J, Romero S, Grasa E, Mena E, Carrió I, Barbanoj MJ. Increased frontal and paralimbic activation following ayahuasca, the pan-Amazonian inebriant. Psychopharmacology (Berl). 2006; 186: 93-98 (Pubitemid 43668314)
49. Rohanová M, Pálenícek T, Balíková M. 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. 2008; 178: 29-36
50. Roussel O, Perrin M, Herard P, Chevance M, Arpin P. Is 4-methylephedrone, an "Ecstasy" of the twenty first century?. Ann Toxicol Anal. 2009; 21: 169-177
51. Saferparty Warnungen (2009) Available at: http://www.saferparty.ch/ download/file/Warnungen%20PDF%202009/XTC-2CB-August-2009.pdf (accessed 12 October 2010).
52. Sanders B, Lankenau SE, Bloom JJ, Hathazi D. "Research chemicals": tryptamine and phenethylamine use among high-risk youth. Subst Use Misuse. 2008; 43: 389-402 (Pubitemid 351448725)
53. SherdleyRGreenwellM (2009) Ten in hospital after 2C-B rave. Nottingham Post. Available at: http://www.thisisnottingham.co.uk/news/hospital-2C-B-rave/ article-1428533-detail/article.html (accessed on 1 December 2010).
54. Shulgin AT, Carter MF. Centrally active phenethylamines. Psychopharm Commun. 1975; 1: 93-98
55. Shulgin A, Shulgin A PIHKAL: A chemical love story. Berkeley, CA: Transform Press; 1991 :
56. Shulgin A, Shulgin A TIHKAL: The continuation. Berkeley, CA: Transform Press; 1997 :
57. Soares ME, Carvalho M, Carmo H, Remiao F, Carvalho F, Bastos ML. Simultaneous determination of amphetamine derivatives in human urine after SPE extraction and HPLC-UV analysis. Biomed Chromatogr. 2004; 18: 125-131 (Pubitemid 38444499)
58. Strassman RJ, Qualls CR, Uhlenhuth EH, Kellner R. Dose-response study of N,N-dimethyltryptamine in humans. II. Subjective effects and preliminary results of a new rating scale. Arch Gen Psychiatry. 1994; 51: 98-108 (Pubitemid 24054311)
59. Takahasi M, Nagashima M, Suzuki J, Seto T, Yasuda I, Yoshida T. Analysis of phenylethylamines and tryptamines in designer drugs using gas chromatography-gas spectrometry. J Health Sci. 2008; 54: 80-96
60. Tanaka E, Kamata T, Katagi M, Tsuchihashi H, Honda KA. Fatal poisoning with 5-MeO-DIPT, foxy. Forens Sci Int. 2006; 163: 152-154
61. United Nations Office on Drugs and Crime (2010) World Drug Report 2010. Vienna. Available at: http://www.unodc.org/documents/wdr/WDR-2010/World-Drug- Report-2010-lores.pdf (accessed 12 December 2010).
62. US Department of Justice (2001) 2C-B (Nexus) Reappears on the Club Drug Scene. National Drug Intelligence Centre Information Bulletin, May 2001. Available at: http://www.erowid.org/chemicals/2cb/2cb-doj-2001-bulletin.pdf (accessed on 1 December 2010).
63. Voorspoels S, Coucke V, Covaci A, Maervoet J, Schepens P, De Meyere C, et al. Resurgence of a lethal drug: paramethoxyamphetamine deaths in Belgium. J Toxicol Clin Toxicol. 2002; 40: 203-204 (Pubitemid 34755591)
64. Wohlfarth A, Weinmann W, Dresen S. LC-MS/MS screening method for designer amphetamines, tryptamines, and piperazines in serum. Anal Bioanal Chem. 2010; 396: 2403-2414
65. Wood DM, Looker JJ, Shaikh L, Button J, Puchnarewicz M, Davies S, et al. Delayed onset of seizures and toxicity associated with recreational use of Bromo-dragonFLY. J Med Toxicol. 2009; 5: 226-229