Bromo-DragonFLY
Encyclopedia
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. It is explicitly illegal only in Sweden
, 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.
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.
activity at the 5-HT2A
serotonin receptor
. Bromo-DragonFLY also has a high binding
affinity for the 5-HT2B and 5-HT2C serotonin
receptor
s, 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.
. It has been sold in the form of blotter
s, 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 following a single large dose, with a slow onset of action that can take up to 6 hours before the effects are felt.
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
, Sweden
,
Denmark
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.
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.
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
. Seizure
s have also been reported.
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"
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.
, 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.
Psychedelic
The term psychedelic is derived from the Greek words ψυχή and δηλοῦν , translating to "soul-manifesting". A psychedelic experience is characterized by the striking perception of aspects of one's mind previously unknown, or by the creative exuberance of the mind liberated from its ostensibly...
hallucinogenic drug
Psychedelics, dissociatives and deliriants
This general group of pharmacological agents can be divided into three broad categories: psychedelics, dissociatives, and deliriants. These classes of psychoactive drugs have in common that they can cause subjective changes in perception, thought, emotion and consciousness...
related to the phenethylamine
Phenethylamine
Phenylethylamine or phenethylamine is a natural monoamine alkaloid, trace amine, and also the name of a class of chemicals with many members well known for psychoactive drug and stimulant effects. Studies suggest that phenylethylamine functions as a neuromodulator or neurotransmitter in the...
family. Bromo-DragonFLY is considered an extremely potent hallucinogen, only slightly less potent than LSD
LSD
Lysergic acid diethylamide, abbreviated LSD or LSD-25, also known as lysergide and colloquially as acid, is a semisynthetic psychedelic drug of the ergoline family, well known for its psychological effects which can include altered thinking processes, closed and open eye visuals, synaesthesia, an...
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. It is explicitly illegal only in Sweden
Sweden
Sweden , officially the Kingdom of Sweden , is a Nordic country on the Scandinavian Peninsula in Northern Europe. Sweden borders with Norway and Finland and is connected to Denmark by a bridge-tunnel across the Öresund....
, Norway
Norway
Norway , officially the Kingdom of Norway, is a Nordic unitary constitutional monarchy whose territory comprises the western portion of the Scandinavian Peninsula, Jan Mayen, and the Arctic archipelago of Svalbard and Bouvet Island. Norway has a total area of and a population of about 4.9 million...
and Denmark
Denmark
Denmark is a Scandinavian country in Northern Europe. The countries of Denmark and Greenland, as well as the Faroe Islands, constitute the Kingdom of Denmark . It is the southernmost of the Nordic countries, southwest of Sweden and south of Norway, and bordered to the south by Germany. Denmark...
, although it may be considered a controlled substance analogue under US and Australian drug laws. Bromo-DragonFLY has a stereocenter
Stereocenter
A stereocenter or stereogenic center is an atom, bearing groups such that an interchanging of any two groups leads to a stereoisomer.A chirality center is a stereocenter consisting of an atom holding a set of ligands in a spatial arrangement which is not superposable on its mirror image...
and R-(-)-bromo-DragonFLY is the more active stereoisomer.
History
Bromo-DragonFLY was first synthesized by Matthew Parker in the laboratory of David E. NicholsDavid E. Nichols
David E. Nichols is an American pharmacologist and medicinal chemist.Presently the Robert C. and Charlotte P. Anderson Distinguished Chair in Pharmacology at Purdue University, Nichols has worked in the field of psychoactive drugs since 1969...
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 agonistAgonist
An agonist is a chemical that binds to a receptor of a cell and triggers a response by that cell. Agonists often mimic the action of a naturally occurring substance...
activity at the 5-HT2A
5-HT2A receptor
The mammalian 5-HT2A receptor is a subtype of the 5-HT2 receptor that belongs to the serotonin receptor family and is a G protein-coupled receptor . This is the main excitatory receptor subtype among the GPCRs for serotonin , although 5-HT2A may also have an inhibitory effect on certain areas such...
serotonin receptor
5-HT receptor
The serotonin receptors, also known as 5-hydroxytryptamine receptors or 5-HT receptors, are a group of G protein-coupled receptors and ligand-gated ion channels found in the central and peripheral nervous systems. They mediate both excitatory and inhibitory neurotransmission...
. Bromo-DragonFLY also has a high binding
Binding (molecular)
Molecular binding is an attractive interaction between two molecules which results in a stable association in which the molecules are in close proximity to each other...
affinity for the 5-HT2B and 5-HT2C serotonin
Serotonin
Serotonin or 5-hydroxytryptamine is a monoamine neurotransmitter. Biochemically derived from tryptophan, serotonin is primarily found in the gastrointestinal tract, platelets, and in the central nervous system of animals including humans...
receptor
Receptor (biochemistry)
In biochemistry, a receptor is a molecule found on the surface of a cell, which receives specific chemical signals from neighbouring cells or the wider environment within an organism...
s, 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.
Dosage
The typical dose of Bromo-DragonFLY is not known, however it has varied from 500 μg to 1 mg. It has about 300 times the potency of mescaline, or 1/5 the potency of LSDLSD
Lysergic acid diethylamide, abbreviated LSD or LSD-25, also known as lysergide and colloquially as acid, is a semisynthetic psychedelic drug of the ergoline family, well known for its psychological effects which can include altered thinking processes, closed and open eye visuals, synaesthesia, an...
. It has been sold in the form of blotter
Blotter
Blotter can mean several things:-*For a desk blotter, see desk pad*For blotter acid, see LSD*For an antique blotter associated with a quill pen, see fountain pen and blotting paper....
s, 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 following a single large dose, with a slow onset of action that can take up to 6 hours before the effects are felt.
Toxicity
Norway
Norway , officially the Kingdom of Norway, is a Nordic unitary constitutional monarchy whose territory comprises the western portion of the Scandinavian Peninsula, Jan Mayen, and the Arctic archipelago of Svalbard and Bouvet Island. Norway has a total area of and a population of about 4.9 million...
, Sweden
Sweden
Sweden , officially the Kingdom of Sweden , is a Nordic country on the Scandinavian Peninsula in Northern Europe. Sweden borders with Norway and Finland and is connected to Denmark by a bridge-tunnel across the Öresund....
,
Denmark
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
2C-B-FLY
2C-B-FLY is a psychedelic phenethylamine of the 2C family. It was first synthesized by Aaron P. Monte.-Chemistry:2C-B-FLY is 8-bromo-2,3,6,7-benzo-dihydro-difuran-ethylamine. The full name of the chemical is 2-ethanamine...
, 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.
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
Necrosis
Necrosis is the premature death of cells in living tissue. Necrosis is caused by factors external to the cell or tissue, such as infection, toxins, or trauma. This is in contrast to apoptosis, which is a naturally occurring cause of cellular death...
and gangrene
Gangrene
Gangrene is a serious and potentially life-threatening condition that arises when a considerable mass of body tissue dies . This may occur after an injury or infection, or in people suffering from any chronic health problem affecting blood circulation. The primary cause of gangrene is reduced blood...
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
2,5-Dimethoxy-4-bromoamphetamine
DOB, also known as Brolamfetamine and Bromo-DMA, is a psychedelic hallucinogenic drug and a substituted amphetamine of the phenethylamine class of compounds, which can be used as an entheogen. DOB was first synthesized by Alexander Shulgin in 1967...
. Treatment was of limited efficacy in this case although tolazoline
Tolazoline
Tolazoline is a non-selective competitive α-adrenergic receptor antagonist. It is a vasodilator that is used to treat spasms of peripheral blood vessels...
is reportedly an effective treatment where available.
Overdoses, disturbing experiences
Bad trip
Bad trip is a disturbing experience sometimes associated with use of a psychedelic drug such as LSD, Salvinorin A, DXM, mescaline, psilocybin, DMT and sometimes even other drugs including cannabis, alcohol and MDMA....
, and Bromo-DragonFLY associated health problems have been described. One case in 2008 in England involved inhalation of vomit, causing nearly fatal asphyxia
Asphyxia
Asphyxia or asphyxiation is a condition of severely deficient supply of oxygen to the body that arises from being unable to breathe normally. An example of asphyxia is choking. Asphyxia causes generalized hypoxia, which primarily affects the tissues and organs...
. Seizure
Convulsion
A convulsion is a medical condition where body muscles contract and relax rapidly and repeatedly, resulting in an uncontrolled shaking of the body. Because a convulsion is often a symptom of an epileptic seizure, the term convulsion is sometimes used as a synonym for seizure...
s have also been reported.
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"
On May 7, 2011, in the United States, two young adults died after overdosing on Bromo-DragonFLY, which they thought was 2C-E
2C-E
2C-E is a psychedelic and phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin. 2C-E is typically found as a white crystalline powder....
, 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.
Sweden
Bromo-DragonFLY was classified as a "health hazard" in Sweden on July 15, 2007, making it illegal to sell or possess there.Denmark
On December 3, 2007 the drug was banned in Denmark. The substance has been declared illegal by health minister Jakob Axel NielsenJakob Axel Nielsen
Jakob Axel Nielsen is a Danish lawyer and politician representing the Conservative People's Party. He has been a member of the Folketing since the 2005 election and was Minister of Traffic and of Energy in the Cabinet of Anders Fogh Rasmussen II from 12 September 2007 to 23 November 2007, and...
, 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.
Norway
Bromo-DragonFLY is currently on the Norwegian narcotics list,. 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.Australia
As of 9 September 2011, Bromo-DragonFLY was added to Schedule 2 of the Queensland Drugs Misuse Regulation 1987.See also
- 2C-B2C-B2C-B or 4-bromo-2,5-dimethoxyphenethylamine is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin in 1974. In Shulgin's book PiHKAL, the dosage range is listed as 16–24 mg. 2C-B is sold as a white powder sometimes pressed in tablets or gel caps and is referred...
- DOB2,5-Dimethoxy-4-bromoamphetamineDOB, also known as Brolamfetamine and Bromo-DMA, is a psychedelic hallucinogenic drug and a substituted amphetamine of the phenethylamine class of compounds, which can be used as an entheogen. DOB was first synthesized by Alexander Shulgin in 1967...
- 2C-B-FLY2C-B-FLY2C-B-FLY is a psychedelic phenethylamine of the 2C family. It was first synthesized by Aaron P. Monte.-Chemistry:2C-B-FLY is 8-bromo-2,3,6,7-benzo-dihydro-difuran-ethylamine. The full name of the chemical is 2-ethanamine...
- 5-HT2A receptor5-HT2A receptorThe mammalian 5-HT2A receptor is a subtype of the 5-HT2 receptor that belongs to the serotonin receptor family and is a G protein-coupled receptor . This is the main excitatory receptor subtype among the GPCRs for serotonin , although 5-HT2A may also have an inhibitory effect on certain areas such...
- PiHKALPiHKALPiHKAL: A Chemical Love Story is a book by Dr. Alexander Shulgin and Ann Shulgin which was published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens...