The dose range of Bromo-DragonFLY is not precisely known, but typical doses are in the range of 100 to 1,000μgorally.[1][2][3][10] However, a death has been reported at approximately 700μg Bromo-DragonFLY.[10] Itsonset can be delayed by up to 6hours and itsduration is in the range of 12 to 24hours for many users, but can be up to 2 to 3days.[2][3][1] The drug's effects include profoundhallucinations andvisual distortions, sound alterations, a sense of connection or belonging with other realities, a sense of peace andwell-being, emotional stimulation, and meeting with entities.[1]
4BDF Bromo Dragonfly powder. The pink color is most likely due to an impurity. The color of pure Bromo Dragonfly BDF is usually white to off-white.[citation needed]
Thetoxicity of Bromo-DragonFLY appears to be fairly high for humans, with reports of at least five deaths believed to have resulted from Bromo-DragonFLY inNorway,[11]Sweden,[12][13]Denmark,[14][15]Finland[16]and the United States.
Laboratory testing has confirmed that in October 2009, a batch of Bromo-DragonFLY was distributed, mislabeled as the related compound2C-B-FLY, which is around 20 times less potent than BDF by weight. This mistake is believed to have contributed to several lethal overdoses and additional hospitalizations. The batch implicated in these deaths also contained significant synthesis impurities, which may have contributed to the toxicity.[17]
Vasoconstrictive action resulting from severe overdose of Bromo-DragonFLY is known to have caused tissuenecrosis of the extremities in at least one case. In September 2007, a 35-year-old Swedish male required amputation of the front part of his feet and several fingers on one hand after taking a massive (but unknown) overdose; reportedly, the compound acted as a long-acting efficacious vasoconstrictor, leading to necrosis andgangrene which became apparent several weeks after the overdose occurred. Treatment was of limited efficacy in this case, althoughtolazoline is reportedly an effective treatment where available.[18][19]
Overdose-associateddisturbing experiences and health problems have been described. One case in 2008 in England involved inhalation of vomit, causing nearly fatalasphyxia.[20]Seizures have also been reported.[21]
On October 3, 2009, a 22-year-old male from Copenhagen died after ingesting Bromo-DragonFLY. His friend described the trip saying, "It was like being dragged to hell and back again. Many times. It is the most evil [thing] I've ever tried. It lasted an eternity."[22]
On May 7, 2011, in the United States, two young adults died after overdosing on Bromo-DragonFLY, which they thought was2C-E, and several others were hospitalized during the same incident. Because they took a dosage appropriate for 2C-E, those who took the drug received, in some cases, 100 times the normal dose. Both deaths followed seizures, vomiting blood, and terrifying hallucinations.[23]
The firstchemical synthesis of racemic Bromo-DragonFLY was reported byDavid E. Nichols in 1998 and was an expansion upon earlier research into the tetrahydrobenzodifuran analogue ofDOB.[6] The 1998 synthesis of racemic Bromo-DragonFLY starts from hydroquinone, which is dialkylated with 1-bromo-2-chloroethane, brominated, and treated with n-butyllithium to yield the tetrahydrobenzodifuran ring system. After formylation of the ring system, the nitropropene derivative was obtained by condensation with nitroethane under ammonium acetate catalysis. The nitropropene derivative was then reduced with lithium aluminium hydride to yield the amine intermediate, which was protected with trifluoroacetic anhydride. Followingpara-bromination with elemental bromine and oxidation of the tetrahydrobenzodifuran ring system withDDQ, the trifluoroacetyl protecting group of the amine was removed to give Bromo-DragonFLY as a racemic mixture of theR andS enantiomers.
In 2001,David E. Nichols reported an enantiospecific synthesis of Bromo-DragonFLY which allowed the individualR andS enantiomers to be studied.[26] Further research determined that (R)-(-)-Bromo-DragonFLY possessed greater binding affinity at the5-HT2A and5-HT2C receptors than (S)-(-)-Bromo-DragonFLY. To synthesize the more activeR enantiomer, a derivative of D-alanine was reacted with 2,3,6,7-tetrahydrobenzodifuran in aFriedel–Crafts acylation, yielding an intermediate containing a β-keto moiety which was removed by treatment with triethylsilane in trifluoroacetic acid. Afterpara-bromination and oxidation of the ring system withDDQ, the amine was deprotected yielding (R)-(-)-Bromo-DragonFLY.
The 1998 synthesis of Bromo-DragonFLY by Nichols et al.[6]
The 2001 enantiospecific synthesis of (R)-(-)-Bromo-DragonFLY by Nichols et al.[26]
Bromo-DragonFLY was first synthesized byDavid E. Nichols and colleagues in 1998.[6] As with the earlier and less potentdihydrofuran series of compounds nicknamedFLY, Bromo-DragonFLY was named after its superficial structural resemblance to adragonfly.[citation needed]
Internationally Bromo DragonFLY is an Unscheduled drug because is not into the Convention on Psychotropic substances of 1971 however still could be controlled for the analogue laws in some countries or for the sale of toxic substances for human consumption.
As of 9 September 2011, Bromo-DragonFLY was added to Schedule 2 of the Queensland Drugs Misuse Regulation 1987.[27]
Nationally, the drug is listed under Schedule 9 (Prohibited) of the Poisons Standard. Accordingly, the drug is prohibited in all states and territories.[28]
As of Oct 12, 2016, Bromo-DragonFLY is listed in Schedule III of the CanadianControlled Drugs and Substances Act: "2C-phenethylamines and their salts, derivatives, isomers and salts of derivatives and isomers", a broad definition which corresponds to anything with a 2,5-dimethoxyphenethylamine core, including (but not limited to) the2C family (includinge.g.βk-2C-B), theDOx chemical class, theTMA family, AlephakaDOT,NBOMe, the25x-NBx series, and of course, Bromo-DragonFLY itself (seethis article).
On December 3, 2007, the drug was banned in Denmark.[29] The substance has been declared illegal by health ministerJakob Axel Nielsen, following recommendations from the Danish Health Ministry. It is currently classified as a dangerous narcotic and therefore its possession, manufacture, importation, supply or usage is strictly prohibited. Anyone involved in such activities can face legal action.[30]
Sveriges riksdag added Bromo-Dragonfly to schedule IV ("substances, plant materials and fungi that hasn't any or without nothing medical use") as narcotics in Sweden as of Jan 3, 2008, published byMedical Products Agency in their regulation LVFS 2007:14 listed as Bromo-Dragonfly, brombensodifuranyl-isopropylamin.[35] Bromo-DragonFLY was first classified as "health hazard" bySveriges riksdags health ministry Statens folkhälsoinstitut under the act Lagen om förbud mot vissa hälsofarliga varor (translatedAct on the Prohibition of Certain Goods Dangerous to Health) as of Jul 15, 2007, in their regulation SFS 2007:600 listed as brombensodifuranylisopropylamin (Bromo-Dragonfly), making it illegal to sell, purchase, buy, retail or possess.[36]
Bromo-DragonFLY is widely reported by the media as being a Class A drug.[20] However, as of 2014, it remains unclear to what extent it is covered by the UK phenylethylamine catch-all clause, with commentators noting both the structural similarities[37] and differences[38][unreliable source?] to the phenylethylamine class. If the prosecution could demonstrate structural similarity in court, it would be considered a Class A substance[39] but as a benzodifuran it is significantly different to this class. It is not explicitly named in the misuse of drugs act.[40] It would be covered by the UKPsychoactive Substances Act 2016 but only if it is sold or traded for human consumption.
Bromo-DragonFLY is unscheduled at federal level in the United States, but could possibly be prosecuted under theFederal Analogue Act if it is sold for human consumption due to its similarities with2C-B andDOB. Bromo-DragonFLY is listed as aSchedule I substance in Oklahoma.[41]
^abcdefghijklmnoCorazza O, Schifano F, Farre M, Deluca P, Davey Z, Torrens M, et al. (May 2011). "Designer drugs on the internet: a phenomenon out-of-control? the emergence of hallucinogenic drug Bromo-Dragonfly".Curr Clin Pharmacol.6 (2):125–129.doi:10.2174/157488411796151129.PMID21592070.
^abcdHill SL, Thomas SH (October 2011). "Clinical toxicology of newer recreational drugs".Clin Toxicol (Phila).49 (8):705–719.doi:10.3109/15563650.2011.615318.PMID21970769.According to user websites, a typical BromodragonFLY dose is 0.2–1 mg with an onset of action of up to 6 h and duration of action of 2 or 3 days (Psychonaut web mapping 2010).66
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^abcdefParker MA, Marona-Lewicka D, Lucaites VL, Nelson DL, Nichols DE (December 1998). "A novel (benzodifuranyl)aminoalkane with extremely potent activity at the 5-HT2A receptor".Journal of Medicinal Chemistry.41 (26):5148–5149.doi:10.1021/jm9803525.PMID9857084.
^abNoble C, Holm NB, Mardal M, Linnet K (October 2018). "Bromo-dragonfly, a psychoactive benzodifuran, is resistant to hepatic metabolism and potently inhibits monoamine oxidase A".Toxicology Letters.295:397–407.doi:10.1016/j.toxlet.2018.07.018.PMID30036687.S2CID51714119.
^Thorlacius K, Borna C, Personne M (2008). "[Bromo-dragon fly--life-threatening drug. Can cause tissue necrosis as demonstrated by the first described case]".Läkartidningen.105 (16):1199–1200.PMID18522262.
^Corazza O, Schifano F, Farre M, Deluca P, Davey Z, Torrens M, et al. (May 2011). "Designer drugs on the internet: a phenomenon out-of-control? the emergence of hallucinogenic drug Bromo-Dragonfly".Current Clinical Pharmacology.6 (2):125–129.doi:10.2174/157488411796151129.hdl:2299/10464.PMID21592070.
^abMcLean TH, Chambers JJ, Parrish JC, Braden MR, Marona-Lewicka D, Kurrasch-Orbaugh D, et al. (July 2006). "C-(4,5,6-trimethoxyindan-1-yl)methanamine: a mescaline analogue designed using a homology model of the 5-HT2A receptor".Journal of Medicinal Chemistry.49 (14):4269–4274.doi:10.1021/jm060272y.PMID16821786.
^Psychonaut Webmapping Research Group."Bromo-Dragonfly Report"(PDF).www.psychonautproject.eu/. Institute of Psychiatry, London.Archived(PDF) from the original on 15 May 2012. Retrieved12 June 2014.
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