Benzofurans and Benzodifurans

Novel Psychoactive Substances: Classification, Pharmacology and Toxicology

Volumn , Issue , 2013, Pages 383-392

  Greene, Shaun L ^a  

^a Victorian Poisons Information Centre   (Australia)

Author keywords

2 CB FLY; 5 APB; 6 APB; Benzodifuran; Benzofuran; Bromo dragonFLY

Indexed keywords

EID: 84903804184     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-12-415816-0.00016-X     Document Type: Chapter

References (43)

1. Mustafa A The chemistry of heterocyclic compounds, benzofurans. Chemistry of heterocyclic compounds: a series of monographs 1974, Vol 29. Wiley-Interscience, New York, p 1-2.
2. Legal Highs Forum. Available: <> [accessed 11.09.12]. http://www.legalhighsforum.com/showthread.php?12738-5apb.
3. Erowid Experience Vaults. Available: <> [accessed 11.09.12]. http://www.erowid.org/experiences/subs/exp_6APB.shtml.
4. Acuna-Castillo C, Villalobos C, Moya PR, Saez P, Cassels BK, Huidobro-Toro JP Differences in potency and efficacy of a series of phenylisopropylamine/phenethylamine pairs at 5-HT2a and 5-HT2 receptors. Brit J Pharmacol 2002, 136:510-519.
5. Hill SL, Thomas SHL Clinical toxicology of newer recreational drugs. Clin Toxicol 2011, 49:705-719.
6. Monte AP, Marona-Lewicka D, Cozzi NV, Nichols DE Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-methylenedioxyamphetamine. J Med Chem 1993, 36:3700-3706.
7. Monte AP, Marona-Lewicka D, Parker MA, Wainscott DB, Nelson DL, Nichols DE Dihydrobenzofuran analogues of hallucinogens. 3. Models of 4-substituted (2,5-dimethoxyphenyl) alkylamine derivatives with rigidified methoxy groups. J Med Chem 1996, 39:2953-2961.
8. Parker MA, Marona-Lewicka D, Lucaites VL, Nelson DL, Nichols DE A novel (benzodifuranyl)aminoalkane with extremely potent activity at the 5-HT2A receptor. J Med Chem 1998, 41:5148-5149.
9. Erowid. Available: <> [accessed 29.01.12]. http://www.erowid.org/chemicals/.
10. Blue Light Forum. Available: <> [accessed 11.09.12]. http://www.bluelight.ru/vb/threads/525471-6-APB-report-from-an-ickle-noob.
11. Drugs Forum. Available at <> [accessed 11.09.12]. http://www.drugs-forum.com/forum/showwiki.php?title=6-APB.
12. Drugs Forum. Available: <> [accessed 11.09.12]. http://www.drugs-forum.com/forum/showthread.php?t=154505.
13. Erowid. Erowid Experience Vaults. Available: <> [accessed 29.01.12]. http://www.erowid.org/experiences/exp_front.shtml.
14. Wikipedia APB. Available: <> [accessed 11.09.12]. http://en.wikipedia.org/wiki/6-APB.
15. Briner K, Burkhart JP, Burkholder TM, et al. Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists. 7045545 (US patent). Published 2000-01-19, issued 2006-16-03.
16. Parker MA. Studies of the perceptiotropic phenethylamines: determinants of affinity for the 5-HT2 receptor. A Thesis submitted to the faculty of Prude University 1998. Available: <> [accessed 29.01.12]. http://bitnest.ca/external.php?id=%251C%2B95%2522%250D%2519%2518%2505%250C%250Dtz%257D%2500%2501.
17. Chambers JJ, Kurrasch-Orbaugh DM, Parker MA, Nichols DE Enantiospecific synthesis and pharmacological evaluation of a series of super-potent, conformationally restricted 5-HT(2A/2C) receptor agonists. J Med Chem 2001, 44:1003-1010.
18. Erowid. Available: <> [accessed 29.01.12]. http://www.erowid.org/chemicals/2cb_fly/2cb_fly.shtml.
19. Nichols DE Medicinal chemistry and structure activity relationships. Amphetamine and its analogs. Psychopharmacology, toxicology and abuse 1994, 3-33. Academic Press, San Diego, CA. A.K. Cho, D.S. Segal (Eds.).
20. Drugs Forum Bromo-dragonfly. Available: <> [accessed 29.01.12]. http://www.drugs-forum.com/forum/showwiki.php?title=Bromo-dragonfly.
21. Erowid. The Vaults of Erowid. Available at <> [accessed 29.01.12]. http://www.erowid.org/chemicals/bromo_dragonfly/bromo_dragonfly.shtml.
22. May JA, McLaughlin MA, Sharif NA, Hellberg MR, Dean TR Evaluation of the ocular hypotensive response to serotonin 5-HT1A and 5-HT2A receptor ligands in conscious ocular hypertensive cynomolgus monkey. J Pharmacol Exp Ther 2003, 306:301-309. [accessed 29.01.12].
23. Herbal Highs. Available at <> [accessed 11.09.12]. http://forum.herbalhighs.com/showthread.php?tid=6708&page=6.
24. Blue Light Forum. Available: <> [accessed 11.09.12]. http://www.bluelight.ru/vb/threads/603896-5-APB-a-functional-and-fun-alternative-to-MDMA.
25. Drugs Forum. Available; <> [accessed 11.09.12]. http://www.drugs-forum.com/forum/showthread.php?t=168765.
26. Blue Light Forum. Available: <> [accessed 11.09.12]. http://www.bluelight.ru/vb/threads/622605-My-5-6-APB-experiences-after-months-and-5-5g-s.
27. Drugs Forum. Available: <> [accessed 11.09.12]. http://www.drugs-forum.com/forum/showthread.php?t=178526.
28. 2012 Global Drug Survey. Available: <>. http://globaldrugsurvey.com/run-my-survey/2012-global-drug-survey.
29. Psychonaut Web Mapping Project. Alert on new recreational drugs on the web; building up a European-wide Web scanning system. Final Report 2010 Available: <> [accessed 29.09.12]. http://www.psychonautproject.eu/reports/Psychonaut_Project_Executive_Summary.pdf.
30. European information system and database on new drugs. Available: <> [accessed 29.01.12]. http://ednd.emcdda.europa.eu/html.cfm/index7246EN.html?SUB_ID=36.
31. European information system and database on new drugs. Available: <> [accessed 29.01.12]. http://ednd.emcdda.europa.eu/html.cfm/index7246EN.html?SUB_ID=41.
32. Europol 2010 Annual Report on the implementation of Council Decision 2005/387/JHA. Available: <> [accessed 29.01.12]. http://www.emcdda.europa.eu/publications/implementation-reports/2010.
33. Baron M, Elie M, Elie L An analysis of legal highs: do they contain what it says on the tin?. Drug Test Anal 2011, 3:576-581.
34. Blue Light Forum. Available: <> [accessed 11.09.12]. http://www.bluelight.ru/vb/threads/635761-Adverse-Reaction-to-5-APB-Please-Read.
35. Personne M, Hulten P Bromo-dragonfly: a life threatening designer drug. Clin Tox 2008, 46:379-380.
36. Thorlacius K, Borna C, Personne M Bromo-dragon fly-life-threatening drug. Can cause tissue necrosis as demonstrated by the first described case. Lakartidningen 2008, 105:199-200.
37. Dargan P, Wood D. Technical profile of Bromo-DragonFLY. EMCDDA Publication. Available: 2010 [accessed 29.01.12]. http://ednd.emcdda.europa.eu/assets/upload/showfile?filename=BDF_Tech_Prof_EMCDDA_Mar_2010.pdf.
38. Wood DM, Looker JJ, Shaikh L, et al. Delayed onset of seizures and toxicity associated with recreational use of bromo-dragonfly. J Med Toxicol 2009, 5:226-229.
39. Nielsen VT, Høgberg LC, Behrens JK Bromo-dragonfly poisoning of 18-year-old male. Ugeskr Laeger 2010, 172:1461-1462.
40. Andreasen MF, Telving R, Birkler RI, Schumacher B, Johannsen M A fatal poisoning involving Bromo-Dragonfly. Forensic Sci Int 2009, 183:91-96.
41. Erowid. Reported GHB-related death may not have been GHB: Bromo-Dragonfly is confirmed by toxicology. Available: <> [accessed 29.01.12]. http://www.erowid.org/chemicals/bromo_dragonfly/bromo_dragonfly_death2.shtml.
42. News on 6. Available: <> [accessed 29.01.12]. http://www.newson6.com/story/14641463/second-victim-dies-after-taking-designer-drug-in-konawa.
43. Erowid. Information on reported deaths related to 2C-B-Fly: misidentified substance is most likely bromo-dragonfly. Available: <> [accessed 29.01.12]. http://www.erowid.org/chemicals/2cb_fly/2cb_fly_death1.shtml.