Bromo-DragonFLY
| Bromo-DragonFLY |
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(2R)-1-(4-bromofuro[2,3-f][1]benzofuran-8-yl)propan-2-amine
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Other names
Bromo-benzodifuranyl-isopropylamine
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| Identifiers |
| CAS number |
502759-67-3 N |
| PubChem |
10544447 |
| Jmol-3D images |
Image 1 |
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C[C@H](CC1=C2C=COC2=C(C3=C1OC=C3)
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InChI=1S/C13H12BrNO2/c1-7(15)6-10-8-2-4-17-13(8)11(14)9-3-5-16-12(9)10/h2-5,7H,6,15H2,1H3/t7-/m1/s1 N
Key: GIKPTWKWYXCBEC-SSDOTTSWSA-N N
InChI=1/C13H12BrNO2/c1-7(15)6-10-8-2-4-17-13(8)11(14)9-3-5-16-12(9)10/h2-5,7H,6,15H2,1H3/t7-/m1/s1
Key: GIKPTWKWYXCBEC-SSDOTTSWBJ
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| Properties |
| Molecular formula |
C13H12BrNO2 |
| Molar mass |
294.14 g/mol |
| Melting point |
decomposes at 240 °C (hydrochloride)
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N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
| Infobox references |
Bromo-DragonFLY is a psychedelic hallucinogenic drug related to the phenethylamine family. Bromo-DragonFLY is considered an extremely potent hallucinogen, only slightly less potent than LSD with a normal dose in the region of 200 μg to 800 μg, and it has an extremely long duration of action up to several days.[1] It is explicitly illegal only in Sweden,[2] Norway and Denmark, although it may be considered a controlled substance analogue under US and Australian drug laws. Bromo-DragonFLY has a stereocenter and R-(-)-bromo-DragonFLY is the more active stereoisomer.
History
Bromo-DragonFLY was first synthesized by Matthew Parker in the laboratory of David E. Nichols in 1998. As with the earlier and less potent dihydrofuran series of compounds nicknamed FLY, Bromo-DragonFLY was named after its superficial structural resemblance to a dragonfly.
Pharmacology
The hallucinogenic effect of bromo-DragonFLY is mediated by its agonist activity at the 5-HT2A serotonin receptor. Bromo-DragonFLY also has a high binding affinity for the 5-HT2B and 5-HT2C serotonin receptors, and is most accurately described as a non-subtype selective 5-HT2 agonist, as it is actually twice as potent an agonist for 5-HT2C receptors as for 5-HT2A, as well as being less than 5x selective for 5-HT2A over 5-HT2B.[3][4]
Dosage
The typical dose of Bromo-DragonFLY is not known, however it has varied from 500 μg to 1 mg.[1] It has about 300 times the potency of mescaline, or 1/5 the potency of LSD. It has been sold in the form of blotters, similar to the distribution method of LSD, which has led to confusion, and reports of mistakenly consuming Bromo-DragonFly. It has a much longer duration of action than LSD and can last for up to 2–3 days[1] following a single large dose, with a slow onset of action that can take up to 6 hours before the effects are felt.
Toxicity
The toxicity of Bromo-DragonFLY appears to be fairly high for humans when taken in doses above the therapeutic range, with reports of at least five deaths believed to have resulted from Bromo-DragonFLY reported in Norway,[5] Sweden,[6][7] Denmark[8][9], Finland[10] and the United States. Laboratory testing has confirmed that in October 2009, a batch of Bromo-Dragonfly was distributed, mislabeled as the related compound 2C-B-FLY, which is around 20x 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.[11]
Also, a Swedish man had to have the front part of his feet and several fingers on one hand amputated after taking a massive overdose. Apparently the compound acted as a long-acting efficacious vasoconstrictor, leading to necrosis and gangrene which was delayed by several weeks after the overdose occurred. Several other cases have also been reported of severe peripheral vasoconstriction following overdose with Bromo-DragonFLY, and a similar case is also known from DOB. Treatment was of limited efficacy in this case although tolazoline is reportedly an effective treatment where available.[12][13]
Overdoses, disturbing experiences, and Bromo-DragonFLY associated health problems have been described. One case in 2008 in England involved inhalation of vomit, causing nearly fatal asphyxia.[14] Seizures have also been reported.[15]
On October 3, 2009, a 22 year old man 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" [16]
On May 7, 2011, in the United States, two young adults died after overdosing on Bromo-DragonFLY, which they thought was 2C-E, and several others were hospitalized during the same incident. The deaths occurred after a fatal miscalculation in dosage. Those who took the drug received, in some cases, 100x the normal dose. Both deaths were very violent, resulting in massive seizures, vomiting blood, and terrifying hallucinations, and several surviving victims are still suffering from its effects.[17]
Legal status
Sweden
Bromo-DragonFLY was classified as a "health hazard" in Sweden on July 15, 2007, making it illegal to sell or possess there.[18][19]
Denmark
On December 3, 2007 the drug was banned in Denmark.[20] The substance has been declared illegal by health minister Jakob 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.[18]
Norway
Bromo-DragonFLY is currently on the Norwegian narcotics list,.[21][22] Thus it is effectively a narcotic drug by Norwegian law.
Romania
The chemical compound has been added as an illegal substance under the Law 143/2000 on February 10, 2010.[23]
Australia
As of 9 September 2011, Bromo-DragonFLY was added to Schedule 2 of the Queensland Drugs Misuse Regulation 1987. [24]
See also
Notes
- ^ a b c "Erowid Bromo-DragonFly Vault : Dosage". http://www.erowid.org/chemicals/bromo_dragonfly/bromo_dragonfly_dose.shtml.
- ^ "Svensk författningssamling (SFS) - Riksdagen". http://www.riksdagen.se/webbnav/index.aspx?nid=3911&bet=1992:1554.
- ^ Parker 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): 5148–9. doi:10.1021/jm9803525. PMID 9857084.
- ^ Corazza O, Schifano F, Farre M, Deluca P, Davey Z, Torrens M, Demetrovics Z, Di Furia L, Flesland L, Siemann H, Skutle A, Van Der Kreeft P, Scherbaum N. Designer drugs on the internet: a phenomenon out-of-control? the emergence of hallucinogenic drug Bromo-Dragonfly. Current Clinical Pharmacology. 2011 May;6(2):125-9. PMID 21592070
- ^ "Erowid Bromo-Dragonfly Vault : Reported GHB-Related Death Involved Bromo-Dragonfly". http://www.erowid.org/chemicals/bromo_dragonfly/bromo_dragonfly_death2.shtml.
- ^ "Erowid Bromo-Dragonfly Vault : Information about a death reportedly related to Bromo-Dragonfly". http://www.erowid.org/chemicals/bromo_dragonfly/bromo_dragonfly_death1.shtml.
- ^ Kajsa Hallberg (2007-04-03). "Man i 20-årsåldern dog av drogen Dragonfly" (in Swedish). expressen.se (AB Kvällstidningen Expressen). http://www.expressen.se/Nyheter/1.622826. Retrieved 2009-10-30.
- ^ Ritzau (2008-08-24). "Nyt stof har slået dansker ihjel" (in Danish). jp.dk. http://jp.dk/indland/aar/article1418250.ece. Retrieved 2009-10-30.
- ^ Andreasen MF, Telving R, Birkler RI, Schumacher B, Johannsen M. (January 2009). "A fatal poisoning involving Bromo-Dragonfly". Forensic Science International 183 (1-3): 91–6. doi:10.1016/j.forsciint.2008.11.001. PMID 19091499.
- ^ Siukonen, Timo (2012-12-14). "Kassisurman päätekijälle 11,5 vuoden vankeustuomio taposta" (in Finnish). Helsingin Sanomat. http://www.hs.fi/kotimaa/Kassisurman+p%C3%A4%C3%A4tekij%C3%A4lle+115+vuoden+vankeustuomio+taposta/a1305551347404. Retrieved 2012-12-14.
- ^ "Erowid 2C-B-Fly Vault: Death Report". http://www.erowid.org/chemicals/2cb_fly/2cb_fly_death1.shtml.
- ^ Bromo-dragonfly – livsfarlig missbruksdrog (Swedish)
- ^ Thorlacius K, Borna C, Personne M. Bromo-dragon fly--life-threatening drug. Can cause tissue necrosis as demonstrated by the first described case. (Swedish). Lakartidningen. 2008 Apr 16-22;105(16):1199-200. PMID 18522262
- ^ George, Sallie (2008-03-27). "England | Surrey | 'I nearly died from taking £5 hit'". BBC News. http://news.bbc.co.uk/1/hi/england/surrey/7315020.stm. Retrieved 2010-02-08.
- ^ Wood DM, Looker JJ, Shaikh L, Button J, Puchnarewicz M, Davies S, Lidder S, Ramsey J, Holt DW, Dargan PI (December 2009). "Delayed onset of seizures and toxicity associated with recreational use of Bromo-dragonFLY". Journal of Medical Toxicology : Official Journal of the American College of Medical Toxicology 5 (4): 226–9. PMID 19876858.
- ^ "| Danish man died after trip on Chinese drug". Jp.dk. http://jp.dk/indland/kbh/article1884968.ece. Retrieved 2010-02-08.
- ^ [1]
- ^ a b "Erowid Bromo-Dragonfly Vault : Legal Status". http://www.erowid.org/chemicals/bromo_dragonfly/bromo_dragonfly_law.shtml#sweden.
- ^ "Statens folkhälsoinstitut - Två nya droger klassas som hälsofarliga". http://www.fhi.se/templates/page____11295.aspx.
- ^ "Amendment of Executive Order on Euphoriant Substances". Danish Medicines Agency. 2007. http://www.dkma.dk/1024/visUKLSArtikel.asp?artikelID=12407.
- ^ "List of narcotic drugs according to Norwegian law". http://www.lovdata.no/for/sf/ho/to-19780630-0008-001.html.
- ^ "Statens Legemiddelverk about derivates and Bromo-DragonFLY". http://www.legemiddelverket.no/templates/InterPage____57471.aspx.
- ^ "Modified Romanian law 143/2000 on January 10, 2010.". http://www.legestart.ro/Ordonanta-de-urgenta-6-2010-modificarea-completarea-Legii-143-2000-prevenirea-combaterea-traficului-consumului-ilicit-droguri-completarea-Legii-339-2005-regimul-juridic-plantelor-(MzQ3MzAw).htm. Retrieved February 28, 2010.
- ^ "Queensland Drugs Misuse Regulation 1987". http://www.legislation.qld.gov.au/LEGISLTN/CURRENT/D/DrugsMisuseR87.pdf.
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References
External links
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Psychedelics
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Dissociatives
NMDAR antagonists |
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Deliriants
mAChR antagonists |
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| Miscellaneous |
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Agonists: Azapirones: Alnespirone • Binospirone • Buspirone • Enilospirone • Eptapirone • Gepirone • Ipsapirone • Perospirone • Revospirone • Tandospirone • Tiospirone • Umespirone • Zalospirone; Antidepressants: Etoperidone • Nefazodone • Trazodone • Vortioxetine; Antipsychotics: Aripiprazole • Asenapine • Clozapine • Quetiapine • Ziprasidone; Ergolines: Dihydroergotamine • Ergotamine • Lisuride • Methysergide • LSD; Tryptamines: 5-CT • 5-MeO-DMT • 5-MT • Bufotenin • DMT • Indorenate • Psilocin • Psilocybin; Others: 8-OH-DPAT • Adatanserin • Bay R 1531 • Befiradol • BMY-14802 • Cannabidiol • Dimemebfe • Ebalzotan • Eltoprazine • F-11,461 • F-12,826 • F-13,714 • F-14,679 • F-15,063 • F-15,599 • Flesinoxan • Flibanserin • Lesopitron • LY-293,284 • LY-301,317 • MKC-242 • NBUMP • Osemozotan • Oxaflozane • Pardoprunox • Piclozotan • Rauwolscine • Repinotan • Roxindole • RU-24,969 • S 14,506 • S-14,671 • S-15,535 • Sarizotan • SSR-181,507 • Sunepitron • U-92,016-A • Urapidil • Vilazodone • Xaliproden • Yohimbine
Antagonists: Antipsychotics: Iloperidone • Risperidone • Sertindole; Beta blockers: Alprenolol • Cyanopindolol • Iodocyanopindolol • Oxprenolol • Pindobind • Pindolol • Propranolol • Tertatolol; Others: AV965 • BMY-7,378 • CSP-2503 • Dotarizine • Flopropione • GR-46611 • Isamoltane • Lecozotan • Mefway • Metitepine/Methiothepin • MPPF • NAN-190 • PRX-00023 • Robalzotan • S-15535 • SB-649,915 • SDZ 216-525 • Spiperone • Spiramide • Spiroxatrine • UH-301 • WAY-100,135 • WAY-100,635 • Xylamidine
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Agonists: Lysergamides: Dihydroergotamine • Methysergide; Triptans: Almotriptan • Avitriptan • Eletriptan • Frovatriptan • Naratriptan • Rizatriptan • Sumatriptan • Zolmitriptan; Tryptamines: 5-CT • 5-Ethyl-DMT • 5-MT • 5-(Nonyloxy)tryptamine; Others: CP-135,807 • CP-286,601 • GR-46611 • L-694,247 • L-772,405 • PNU-109,291 • PNU-142,633
Antagonists: Lysergamides: Metergoline; Others: Alniditan • BRL-15,572 • Elzasonan • GR-127,935 • Ketanserin • LY-310,762 • LY-367,642 • LY-456,219 • LY-456,220 • Metitepine/Methiothepin • Ritanserin • Yohimbine • Ziprasidone
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Agonists: Phenethylamines: 2C-B • 2C-E • 2C-I • 2C-T-2 • 2C-T-7 • 2C-T-21 • DOB • DOC • DOI • DOM • MDA • MDMA • Mescaline; Piperazines: Aripiprazole • mCPP • TFMPP; Tryptamines: 5-CT • 5-MeO-α-ET • 5-MeO-α-MT • 5-MeO-DET • 5-MeO-DiPT • 5-MeO-DMT • 5-MeO-DPT • 5-MT • α-ET • α-Methyl-5-HT • α-MT • Bufotenin • DET • DiPT • DMT • DPT • Psilocin • Psilocybin; Others: A-372,159 • AL-38022A • CP-809,101 • Dimemebfe • Lorcaserin• Medifoxamine • MK-212 • Org 12,962 • ORG-37,684 • Oxaflozane • PNU-22394 • Ro60-0175 • Ro60-0213 • Vabicaserin • WAY-629 • WAY-161,503 • YM-348
Antagonists: Atypical antipsychotics: Clorotepine • Clozapine • Iloperidone • Melperone • Olanzapine • Paliperidone • Pimozide • Quetiapine • Risperidone • Sertindole • Ziprasidone • Zotepine; Typical antipsychotics: Chlorpromazine • Loxapine • Pipamperone; Antidepressants: Agomelatine • Amitriptyline • Amoxapine • Aptazapine • Etoperidone • Fluoxetine • Mianserin • Mirtazapine • Nefazodone • Nortriptyline • Tedatioxetine • Trazodone; Others: Adatanserin • Cinanserin • Cyproheptadine • Deramciclane • Dotarizine • Eltoprazine • Esmirtazapine • FR-260,010 • Ketanserin • Ketotifen • Latrepirdine • Metitepine/Methiothepin • Methysergide • Pizotifen • Ritanserin • RS-102,221 • S-14,671 • SB-200,646 • SB-206,553 • SB-221,284 • SB-228,357 • SB-242,084 • SB-243,213 • SDZ SER-082 • Xylamidine
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Agonists: Lysergamides: Dihydroergotamine • Ergotamine • Lisuride • LSD • Mesulergine • Metergoline • Methysergide; Tryptamines: 2-Methyl-5-HT • 5-BT • 5-CT • 5-MT • Bufotenin • E-6801 • E-6837 • EMD-386,088 • EMDT • LY-586,713 • N-Methyl-5-HT • Tryptamine; Others: WAY-181,187 • WAY-208,466
Antagonists: Antidepressants: Amitriptyline • Amoxapine • Clomipramine • Doxepin • Mianserin • Nortriptyline; Atypical antipsychotics: Aripiprazole • Asenapine • Clorotepine • Clozapine • Fluperlapine • Iloperidone • Olanzapine • Tiospirone; Typical antipsychotics: Chlorpromazine • Loxapine; Others: BGC20-760 • BVT-5182 • BVT-74316 • Cerlapirdine • EGIS-12,233 • GW-742,457 • Ketanserin • Latrepirdine • Lu AE58054 • Metitepine/Methiothepin • MS-245 • PRX-07034 • Ritanserin • Ro04-6790 • Ro 63-0563 • SB-258,585 • SB-271,046 • SB-357,134 • SB-399,885 • SB-742,457
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Agonists: Lysergamides: LSD; Tryptamines: 5-CT • 5-MT • Bufotenin; Others: 8-OH-DPAT • AS-19 • Bifeprunox • E-55888 • LP-12 • LP-44 • RU-24,969 • Sarizotan
Antagonists: Lysergamides: 2-Bromo-LSD • Bromocriptine • Dihydroergotamine • Ergotamine • Mesulergine • Metergoline • Methysergide; Antidepressants: Amitriptyline • Amoxapine • Clomipramine • Imipramine • Maprotiline • Mianserin; Atypical antipsychotics: Amisulpride • Aripiprazole • Clorotepine • Clozapine • Olanzapine • Risperidone • Sertindole • Tiospirone • Ziprasidone • Zotepine; Typical antipsychotics: Chlorpromazine • Loxapine; Others: Butaclamol • EGIS-12,233 • Ketanserin • LY-215,840 • Metitepine/Methiothepin • Pimozide • Ritanserin • SB-258,719 • SB-258,741 • SB-269,970 • SB-656,104 • SB-656,104-A • SB-691,673 • SLV-313 • SLV-314 • Spiperone • SSR-181,507 • Vortioxetine
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