Bromo-DragonFLY

Bromo-DragonFLY (or 3C-Bromo-Dragonfly, DOB-

[2] Bromo-DragonFLY
Dragonfly ) is a substance related to the phenethylamine family.
Bromo-DragonFLY is considered a potent hallucinogen, having
around one third the potency of 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.[3] Bromo-DragonFLY has a
stereocenter and (R)-(−)-bromo-DragonFLY is the more active
stereoisomer.

Names
Contents IUPAC name
1-(4-Bromofuro[2,3-f]
History
[1]benzofuran-8-yl)propan-2-
Pharmacology amine[1]
Chemistry Other names
Dosage Bromo-benzodifuranyl-
Toxicity isopropylamine

Drug prohibition laws Identifiers

United States CAS Number 502759-67-3 (http
Canada s://commonchemistr
United Kingdom y.cas.org/detail?cas
Sweden _rn=502759-67-3)
Denmark 3D model Interactive image (ht
Norway (JSmol) tps://chemapps.stola
Poland f.edu/jmol/jmol.php?
Romania model=CC%28N%2
Australia 9Cc1c2ccoc2c%28B
Finland r%29c2ccoc12)
See also Interactive image (ht
Notes tps://chemapps.stola
f.edu/jmol/jmol.php?
References
model=CC%28N%2
9CC1%3DC2OC%3
History DCC2%3DC%28Br%
29C2%3DC1C%3DC
O2)
ChEMBL ChEMBL149024 (htt
ps://www.ebi.ac.uk/c
hembldb/index.php/c
Bromo-DragonFLY was first synthesized by Matthew Parker in ompound/inspect/Ch
the laboratory of David E. Nichols in 1998. As with the earlier and EMBL149024)
less potent dihydrofuran series of compounds nicknamed FLY,
ChemSpider 8014776 (https://ww
Bromo-DragonFLY was named after its superficial structural
resemblance to a dragonfly. w.chemspider.com/C
hemical-Structure.80
14776.html)
Pharmacology
8719838 (https://ww
Bromo-DragonFLY also than 5x selective for 5-HT2A over 5- w.chemspider.com/C
hemical-Structure.87
HT2B.[4][5] Bromo-DragonFLY is also a MAO-A inhibitor,[6] and
19838.html) R
thus strongly inhibits oxidative deamination of 5-HT, increasing its
risk profile. 8672089 (https://ww
w.chemspider.com/C
Chemistry hemical-Structure.86
72089.html) S
The first synthesis of racemic Bromo-DragonFLY was reported by PubChem 9839057 (https://pub
David E. Nichols in 1998 and was an expansion upon earlier CID chem.ncbi.nlm.nih.g
research into the tetrahydrobenzodifuran analogue of DOB.[7] The ov/compound/98390
1998 synthesis of racemic Bromo-DragonFLY starts from
57)
hydroquinone, which is dialkylated with 1-bromo-2-chloroethane,
brominated, and treated with n-butyllithium to yield the 10544447 (https://pu
tetrahydrobenzodifuran ring system. After formylation of the ring bchem.ncbi.nlm.nih.
system, the nitropropene derivative was obtained by condensation gov/compound/1054
with nitroethane under ammonium acetate catalysis. The 4447) R
nitropropene derivative was then reduced with lithium aluminum 10496688 (https://pu
hydride to yield the amine intermediate, which was protected with
bchem.ncbi.nlm.nih.
trifluoroacetic anhydride. Following para-bromination with
elemental bromine and oxidation of the tetrahydrobenzodifuran gov/compound/1049
ring system with DDQ, the trifluoroacetyl protecting group of the 6688) S
amine was removed to give Bromo-DragonFLY as a racemic UNII GC9M7R36OI (http
mixture of the R and S enantiomers. s://fdasis.nlm.nih.go
In 2001, David E. Nichols reported an enantiospecific synthesis of v/srs/srsdirect.jsp?re
Bromo-DragonFLY which allowed the individual R and S gno=GC9M7R36OI)
enantiomers to be studied.[8] Further research determined that (R)-
(-)-Bromo-DragonFLY possessed greater binding affinity at the 5- InChI
HT2A and 5-HT2C receptors than (S)-(-)-Bromo-DragonFLY. To
InChI=1S/C13H12BrNO2/c1-7(15)6
synthesize the more active R enantiomer, a derivative of D-alanine -10-8-2-4-17-13(8)11(14)9-3-5-
was reacted with 2,3,6,7-tetrahydrobenzodifuran in a Friedel– 16-12(9)10/h2-5,7H,6,15H2,1H
Crafts acylation, yielding an intermediate containing a β-keto 3
moiety which was removed by treatment with triethylsilane in Key: GIKPTWKWYXCBEC-UHFFFA
trifluoroacetic acid. After para-bromination and oxidation of the OYSA-N
ring system with DDQ, the amine was deprotected yielding (R)-
SMILES
(-)-Bromo-DragonFLY.
CC(N)Cc1c2ccoc2c(Br)c2ccoc12
CC(N)CC1=C2OC=CC2=C(Br)C2=
C1C=CO2

Properties
 Chemical C13H12BrNO2
formula
Molar mass 294.144 g mol−1
log P 2.519
Except where otherwise noted, data
are given for materials in their
standard state (at 25 °C [77 °F],
100 kPa).
verify (what is ?)
Infobox references

The 1997 synthesis of Bromo-DragonFLY by Nichols et al.[7]

The 2001 enantiospecific synthesis of (R)-(-)-Bromo-DragonFLY by Nichols et al.[8]

Dosage
The typical dose of Bromo-DragonFLY is not known, however it has varied from 500 μg to 1 mg.[3] It has
about 300 times the potency of mescaline, or 1/3 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[3] 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,
with reports of at least five deaths believed to have resulted from Bromo-
DragonFLY in Norway,[9] Sweden,[10][11] Denmark,[12][13] Finland[14]
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.[15]
4BDF Bromo Dragonfly
Vasoconstrictive action resulting from severe overdose of Bromo-
powder. The pink color is
DragonFLY is known to have caused tissue necrosis of the extremities in at
most likely due to an
least one case. In September 2007, a 35-year-old Swedish male required
impurity. The color of pure
amputation of the front part of his feet and several fingers on one hand after
Bromo Dragonfly BDF is
taking a massive (but unknown) overdose; reportedly, the compound acted
usually white to off-white,
as a long-acting efficacious vasoconstrictor, leading to necrosis and
similar to most recreational
gangrene which became apparent several weeks after the overdose drugs, so there is no way to
occurred. Treatment was of limited efficacy in this case, although tolazoline distinguish between them by
is reportedly an effective treatment where available.[16][17] eye.

Overdose-associated disturbing experiences and health problems have been

described. One case in 2008 in England involved inhalation of vomit, causing nearly fatal asphyxia.[18]
Seizures have also been reported.[19]

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."[20]

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. Because they
took a dosage appropriate for 2C-E, those who took the drug received, in some cases, 100x the normal
dose. Both deaths followed seizures, vomiting blood, and terrifying hallucinations.[21]

Drug prohibition laws

United States

Bromo-DragonFLY is unscheduled at federal level in the United States but could be prosecuted if it sold for
human consumption, Bromo Dragonfly is listed as a Schedule I in Oklahoma.

Canada
As of Oct 12, 2016, Bromo-DragonFLY is listed in Schedule III of the Canadian Controlled 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) the 2C family (including e.g. βk-2C-B), the DOx chemical class, the TMA
family, Aleph aka DOT, NBOMe, the 25x-NBx series, and of course, Bromo-DragonFLY itself (see this
article (http://www.gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors73-eng.php)).

United Kingdom

Bromo-DragonFLY is widely reported by the media as being a Class A drug.[22] 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[23] and differences[24] to the phenylethylamine class. If
the prosecution could demonstrate structural similarity in court, it would be considered a Class A
substance[25] but as a benzodifuran it is significantly different to this class. It is not explicitly named in the
misuse of drugs act.[26] It would be covered by the UK Psychoactive Substances Act 2016 but only if is
sold or traded for human consumption.

Sweden

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 by
Medical Products Agency in their regulation LVFS 2007:14 listed as Bromo-Dragonfly,
brombensodifuranyl-isopropylamin.[27] Bromo-DragonFLY was first classified as "health hazard" by
Sveriges riksdags health ministry Statens folkhälsoinstitut under the act Lagen om förbud mot vissa
hälsofarliga varor (translated Act 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.[28]

Denmark

On December 3, 2007, the drug was banned in Denmark.[29] 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.[30]

Norway

Bromo-DragonFLY is currently on the Norwegian narcotics list,.[31][32] Thus it is effectively a narcotic

drug by Norwegian law.

Poland

Currently, Bromo-DragonFLY is an uncontrolled substance in Poland.

Romania
The chemical compound has been added as an illegal substance under the Law 143/2000 on February 10,
2010.[33]

Australia

As of 9 September 2011, Bromo-DragonFLY was added to Schedule 2 of the Queensland Drugs Misuse
Regulation 1987.[34]

Nationally, the drug is listed under Schedule 9 (Prohibited) of the Poisons Standard. Accordingly, the drug
is prohibited in all states and territories.[35]

Finland

As of 12 March 2012, Bromo-DragonFLY is an illegal designer drug.[36]

See also
2C-B
DOB
DOB-FLY
2C-B-FLY
5-HT2A receptor
PiHKAL
Ergotism

Notes
1. "Bromo-DragonFLY" (https://web.archive.org/web/20141006082741/http://forendex.southern
forensic.org/index.php/detail/index/1125). Forendex. USA: Southern Association of Forensic
Scientists. Archived from the original (http://forendex.southernforensic.org/index.php/detail/in
dex/1125) on 6 October 2014. Retrieved 16 March 2012.
2. "Erowid Bromo-Dragonfly Vault" (https://www.erowid.org/chemicals/bromo_dragonfly/bromo
_dragonfly.shtml). www.erowid.org. Archived (https://web.archive.org/web/20180323230015/
https://www.erowid.org/chemicals/bromo_dragonfly/bromo_dragonfly.shtml) from the original
on 23 March 2018. Retrieved 26 March 2018.
3. "Erowid Bromo-DragonFly Vault : Dosage" (http://www.erowid.org/chemicals/bromo_dragonf
ly/bromo_dragonfly_dose.shtml). Archived (https://web.archive.org/web/20080322040809/htt
p://www.erowid.org/chemicals/bromo_dragonfly/bromo_dragonfly_dose.shtml) from the
original on 2008-03-22.
4. 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 (https://doi.org/10.
1021%2Fjm9803525). PMID 9857084 (https://pubmed.ncbi.nlm.nih.gov/9857084).
 5. 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 (May 2011).
"Designer drugs on the internet: a phenomenon out-of-control? the emergence of
hallucinogenic drug Bromo-Dragonfly". Current Clinical Pharmacology. 6 (2): 125–9.
doi:10.2174/157488411796151129 (https://doi.org/10.2174%2F157488411796151129).
hdl:2299/10464 (https://hdl.handle.net/2299%2F10464). PMID 21592070 (https://pubmed.nc
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6. Noble C, Holm NB, Mardal M, Linnet K (1 October 2018). "Bromo-dragonfly, a psychoactive
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8. Chambers, James; Kurrasch-Orbaugh, Deborah; Parker, Matthew; Nichols, David (26
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Per, 35, blev stympad av dödsdrogen - Vårdades i respirator i tio dygn efter att ha tagit
Bromo-Dragonfly (https://www.aftonbladet.se/nyheter/article3234876.ab)
 [1] (http://newsok.com/man-gets-prison-sentence-in-partygoers-drug-deaths/article/3700764)
[2] (http://news.bbc.co.uk/1/hi/england/surrey/7315020.stm)

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