Bromo-DragonFLY

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Structural formula
Bromo-DragonFLY
Bromo-DragonFLY
General
Surname Bromo-DragonFLY
other names
  • ( R ) -1- (4-bromofuro [2,3- f ] [1] benzofuran-8-yl) propan-2-amine ( IUPAC )
  • ( R ) -8-Bromo-α-methyl-benzo [1,2- b : 4,5- b ' ] difuran-4-ethanamine
  • DOB-DragonFLY
Molecular formula C 13 H 12 BrNO 2
Brief description

crystalline solid ( hydrochloride )

External identifiers / databases
CAS number
  • 219986-94-4
  • 502759-67-3 ( R -Bromo-DragonFLY)
  • 219986-78-4 (hydrochloride)
PubChem 9839057
Wikidata Q2452973
Drug information
Mechanism of action

Agonist at the 5-HT 2A serotonin receptor

properties
Molar mass 294.14 g mol −1
solubility
  • in DMSO 5 mg / ml
  • in DMF 1 mg / ml
safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Bromo-DragonFLY is a research chemical with hallucinogenic and psychedelic effects, which, due to its structure, is one of the substituted phenethylamines or amphetamines . The effect is attributed, among other things, to the properties of the Bromo-DragonFLY as a potent agonist on the serotonin receptor 5-HT 2A . Bromo-DragonFLY is a derivative of the DOB .

history

Bromo-DragonFLY was developed by Matthew Parker at Purdue University in 1998 . The name comes from the English ( dragonfly , German dragonfly) and describes the appearance of the partial structure of the aromatic with the furan rings .

presentation

Many different synthetic routes are conceivable for the representation of Bromo-DargonFLY. A method described in the literature is shown below as an example:

Synthesis of Bromo-DragonFLY

Pharmacological properties

Pharmacodynamics

Bromo-DragonFLY has a stereocenter , where ( R ) - (-) - Bromo-DragonFLY is the pharmacologically more active stereoisomer . It binds with high affinity to the 5-HT 2A / 2B / 2C serotonin receptors with a K i value of 0.31 nM at the 5-HT 2A receptor and 0.11 nM at the 5-HT 2C receptor. For the ( S ) isomer, K i values ​​of 0.68 nM for the 5-HT 2A receptor and 0.25 nM for the 5-HT 2C receptor are given.

effect

Due to its high affinity for the 5-HT 2A receptor, the effect is comparable to that of LSD or DOB, but the duration of action is significantly increased with up to 96 hours. Fatal overdoses have been reported. There have also been cases in the UK where amputations had to be performed.

Legal status

As a derivative of 2- phenethylamine , Bromo-DragonFLY in Germany is subject to the New Psychoactive Substances Act that came into force in November 2016 . With the exception of the exceptions defined in the law, trading, placing on the market, manufacturing, administering and bringing Bromo-DragonFLY are generally punishable.

In the US bromo-dragonfly is a Schedule I listed. In Canada, all substances with a 2,5-dimethoxyphenylethamine structure have been classified as Schedule III since October 12, 2016 , including most 2Cs, as well as DOx, TMA, Aleph, NBOMes, NBOHs, NBF, bk-2-CB, among others , 2C-B-Fly. In the UK it is treated as a class A drug . In Sweden it is listed as class IV ( LVFS 2007: 14 ). In 2007 it was banned in Denmark. In Norway it is treated as a narcotic. It has been banned in Romania since February 10, 2010. In Australia, it was classified as a Class 2 narcotic on September 9, 2011. In Finland it has been banned as a designer drug since March 12, 2012.

Oddities

At an esoteric seminar for alternative practitioners in Handeloh, Lower Saxony, on September 5, 2015, the 29 participants consumed a mixture of Bromo-DragonFLY and 2C-E , also known as Aquarust. This led to mass poisoning, through which those affected suffered from delusions and seizures, among other things, so that all people in hospitals had to be treated by a doctor. The case then became known throughout Germany. While in the first press reports only the consumption of 2C-E was considered likely, the consumption of Bromo-DragonFLY could also be proven by studies at the forensic medicine institute in Cologne. It was only ingestion that apparently led to the unusually severe effects on the health and habitus of the consumer. The seminar leader stated in court that there was an unknown contamination of the 2C-E, which he gave to the participants, with Bromo-DragonFLY.

literature

  • Matthew A. Parker, David E. Nichols et al .: A Novel (Benzodifuranyl) aminoalkane with Extremely Potent Activity at the 5-HT2A Receptor. In: Journal of Medicinal Chemistry. 41, 1998, pp. 5148-5149, doi: 10.1021 / jm9803525 .
  • Erin C. Reed, Gregory S. Kiddon, US Department of Justice Drug Enforcement Administration: The Characterization of Three FLY Compounds (2C-B-FLY, 3C-B-FLY, and Bromo-DragonFLY). (PDF; 1.3 MB) In: Microgram Journal. Volume 5, Numbers 1-4, 2007.
  • O. Corazza, F. Schifano et al .: Designer drugs on the internet: a phenomenon out-of-control? The emergence of hallucinogenic drug Bromo-Dragonfly. In: Current Clinical Pharmacology. Volume 6, Number 2, May 2011, pp. 125-129, ISSN  2212-3938 . PMID 21592070 .

Web links

Individual evidence

  1. ^ A b c Cayman Chemical: Product Information Bromo-DragonFLY (hydrochloride) , accessed April 16, 2013.
  2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  3. ↑ Brittany Christine Huntington: Synthesis and Intermediate / By-Product Analysis of Bromo-dragonfly, a Dihydrobenzofuran Analogue of Phenethylamine Hallucinogens . California 2007 ( psu.edu [PDF]).
  4. ↑ James J. Chambers, Deborah M. Kurrasch-Orbaugh, Matthew A. Parker, David E. Nichols: Enantiospecific Synthesis and Pharmacological Evaluation of a Series of Super-Potent, Conformationally Restricted 5-HT2A / 2C Receptor Agonists. In: Journal of Medicinal Chemistry. 44, 2001, pp. 1003-1010, doi: 10.1021 / jm000491y .
  5. Jump up ↑ MA Parker, D. Marona-Lewicka, VL Lucaites, DL Nelson, DE Nichols: A novel (benzodifuranyl) aminoalkane with extremely potent activity at the 5-HT2A receptor . In: Journal of Medicinal Chemistry . tape 41 , no. December 26 , 1998, pp. 5148-5149 , doi : 10.1021 / jm9803525 , PMID 9857084 .
  6. ^ A b O. Corazza, F. Schifano, M. Farre, P. Deluca, Z. Davey, M. Torrens, Z. Demetrovics, L. Di Furia, L. Flesland, H. Siemann, A. Skutle, P. Van Der Kreeft, N. Scherbaum: Designer drugs on the internet: a phenomenon out-of-control? the emergence of hallucinogenic drug Bromo-Dragonfly. In: Current Clinical Pharmacology. 6 (2), May 2011, pp. 125-129. PMID 21592070 .
  7. ↑ MF Andreasen, R. Telving, RI Birkler, B. Schumacher, M. Johannsen: A fatal poisoning Involving bromo-dragonfly. In: Forensic science international. Volume 183, Number 1-3, January 2009, pp. 91-96, ISSN  1872-6283 . doi: 10.1016 / j.forsciint.2008.11.001 . PMID 19091499 .
  8. ^ Order Amending Schedule III to the Controlled Drugs and Substances Act (2C-phenethylamines) . In: Canada Gazette . tape 150 , no. 9 , 2016 ( full text ).
  9. ^ Sallie George: 'I nearly died from taking £ 5 hit' . In: BBC News , BBC , March 27, 2008. Retrieved November 28, 2013. 
  10. ↑ Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 1997: 12) om förteckningar över narcotics . In: Läkemedelsverkets författningssamling . 2007 (Swedish, full text [PDF; 89 kB ]).
  11. ^ Amendment of Executive Order on Euphoriant Substances . Danish Medicines Agency . 2007.
  12. ↑ List of narcotic drugs according to Norwegian law .
  13. ↑ Statens Legemiddelverk about derivative and Bromo-Dragonfly . Archived from the original on May 28, 2009.
  14. ↑ Modified Romanian law 143/2000 on January 10, 2010. . Archived from the original on April 23, 2012. Retrieved on February 28, 2010.
  15. ↑ Queensland Drugs Misuse Regulation 1987 .
  16. ↑ Poisons Standard October 2015 .
  17. ↑ Design drugs
  18. ↑ Alternative practitioners took part in the scene drug conference , Spiegel online report from September 5, 2015, accessed on July 7, 2018.
  19. ↑ What did the naturopaths from Handeloh take? , Online report of the Süddeutsche Zeitung of September 7, 2015, accessed on July 7, 2018.
  20. ↑ Alternative practitioners in a frenzy - apparently a therapy trip , online report of the world from September 25, 2015, accessed on July 7, 2018.
  21. ↑ S. Iwersen-Bergmann, S. Lehman, A. Heinemann, C. Schröder, A. Müller, H. Jungs, H. Andresen-Streichert, K. Pueschel, C. Vidal, K. Mercer-Chalmers-Bender: Mass poisoning with NPS: 2C-E and Bromo-DragonFly . In: International Journal of Legal Medicine . 2018, p. 1-7 , doi : 10.1007 / s00414-018-1882-9 .
  22. ^ Mass frenzy of alternative practitioners in Handeloh in court , online report by the Hamburger Abendblatt from November 3, 2017, accessed on July 7, 2018.