Introduction to Bromo-Dragonfly

Bromo-Dragonfly (1-(8-Bromobenzo[1,2-b;4,5-b]difuran-4-yl)-2-aminopropane)[3], also known as DOB-Dragonfly, is an extremely potent and long acting psychedelic. It is one of the most potent non-ergoline psychedelics, with an active dose typically in the mid-to-high microgram range. Early cases of human use regarding this psychedelic amphetamine can be traced to 2001 [2]. It is the benzodifuran analog of the more commonly reported psychedelic amphetamine DOB. The name of the compound is derived from a superficial resemblance of the molecular structure to that of a fly, with the two furan rings on opposing sides of a central phenyl ring forming the wings. Due to the drugs high potency and steep dose-response curve, overdose is a distinct possibility. There have been several severe injuries and fatalities directly attributed to Bromo-Dragonfly overdose. It is closely related to 2C-B-FLY, a non-aromatized phenethylamine analogue. Confusion between Bromo-Dragonfly and 2C-B-FLY has resulted in several hospitalizations and fatalities.

Using Bromo-Dragonfly

Bromo-Dragonfly has been distributed in powder, as well as suspended in liquid solvents. It is typically distributed on blotter paper, though powder and tablets are not unheard of[2]. Given the drugs extreme potency and narrow safety window, accurate measurement of doses is critical, as even a dose of a few milligrams can be life-threatening [3]. Accordingly, a well calibrated analytical scale with resolution to 0.0001g (100ug) is necessary to appropriately measure doses of Bromo-Dragonfly. The best practice for handling such potent compounds is to use a combination of weighing on an appropriate scale followed by re-suspension in an appropriate solvent and volumetric measurement.

There have been varying reactions to different samples of the compound, generalized as distinguishable from European vs. American origin; the European samples have tended to be quite a bit more potent, with threshold doses beginning at 100µg, while threshold doses for the American batches have been reported as high as 500µg[2]. The difference in active dose between these two batches may have been an issue of purity. Alternatively it has been proposed that the 'European' batch was enriched in the more active of the two Bromo-Dragonfly stereoisomers, so was more active than the 'American' racemate. A standard dose of the 'American' batch would be a significantly high dose or even overdose for the 'European' batch. New batches of Bromo-Dragonfly must therefore be treated with extreme caution, and assumed to be maximally potent (i.e. threshold dose ~100µg).

Routes of administration

Oral

The most common reported route of administration is oral. Doses range from 300µg to 1.8mg (this is quite high, and likely reflects diminished potency in samples ingested). Severe complications have arisen at doses greater than 1mg, though definitive dose ranges have not been designated for this compound.

Effects of Bromo-Dragonfly

As a psychedelic amphetamine, Bromo-Dragonfly is a strong hallucinogen with stimulating qualities. Reports suggest psychoactivity may last as long as 36 hours after consumption[2]. The onset of orally dosed Bromo-dragonFLY is typically reported to be very slow, often taking several hours before psychedelic effects are felt. At the height of its psychedelic effect, the intensity of the experience is reported to wax and wane unpredictably. A user may alternate between states of lucidity and extreme psychedelic intoxication multiple times during the experience. The slow onset and oscillatory nature of the experience may lead some users to re-dose, as they may mistakenly believe that they had originally taken a sub-active dose and attempt to 'boost' the effects. Given the high risk associated with overdose, taking multiple doses of Bromo-Dragonfly in a single session is an extremely unsafe practice.

Combinations with Bromo-Dragonfly

Fatalities have been observed concerning the following combinations, though not necessarily attributable to combined action:

Cannabis
Ketamine

Combinations have been noted with the following [2]:

LSD
2C-B
Methylone
Amphetamines
Alprazolam
Cocaine
Kratom
Ethanol

Pharmacology and Pharmacokinetics of Bromo-Dragonfly

Bromo-Dragonfly is a non-selective 5-HT2 receptor agonist with particularly high affinity for the 5-HT2C receptor subtype, though its psychedelic properties are likely attributable to activity at the 5-HT2A receptor subtype. While studies have been performed in rodents, little to no analysis has been recorded in humans. Some evidence supports vasoconstrictive properties, caused by prolonged stimulation of peripheral alpha1 adrenergic receptors [5]. Likely contributing to vasoconstrictive properties is the compounds non-specific, and highly potent, affinity for serotonergic 5-HT2 receptors.

Bromo-Dragonfly receptor binding

In competition binding assays, the R isomer of Bromo-Dragonfly is characterized as having a Ki, nM (SEM) at 5-HT2A and 5-HT2C, using [3H]DOB and [125I]DOI as competitors, of 0.31 (0.042) and 0.11 (0.014), respectively - while the S isomer generated values of 0.68 (0.083) and 0.25 (0.046); accordingly, the R isomer is characterized by higher affinities across both subtypes. In measures of functional activity, Chambers et. al. assessed the capacity of Bromo-Dragonfly to stimulate phosphoinositide hydrolysis in NIH-3T3 cells expressing 5-HT2A receptors, identifying EC50 values (SEM) of 2.7(0.55) and 19(1.6) for the R and S isomers, respectively - demonstrating the R isomer as the more potent[6].

In additional studies, Parker et. al. identified the following Ki values at three receptors, using [125I]DOI and [3H]5-HT[7]; this demonstrates that the drug is characterized by about twice the affinity at the 5-HT2C receptor than 5-HT2A, as well as a far higher affinity at the 5-HT2B receptor than DOI. Compound 3 represents Bromo-Dragonfly, while compound 2 is a modified 2C-B-FLY that has been methylated on the alpha carbon of the ethylamine chain - otherwise known as 'Bromo-FLY', DOB-FLY, or 'dragonfly', which is essentially an unsaturated analogue of Bromo-Dragonfly:

[7]

Values derived from Parker et. al. evaluated the capacity of Bromo-Dragonfly to discriminate the effects of IP injections of saline from those containing either LSD or DOI - calculating potency as ED50 with 95% confidence intervals[7]:


Chambers et. al. propose the heightened potency of Bromo-Dragonfly (and related analogues of compounds considered to be the ‘2C’ series), characterized by more favorable interactions with agonist binding sites, is potentially attributable to increased hydrophobicity of the extended tricyclic aromatic nucleus, and thus a greater tendency to partition into a hydrophobic receptor binding site. Additionally, the extended aromaticity may result in enhanced affinity due to increased aromatic surface area on the ligand available for favorable π-stacking interactions with agonist binding sites, while preserving hydrogen-bond acceptor properties at furan oxygen atoms.

The health risks of Bromo-Dragonfly

Several fatalities attributable to the use of Bromo-Dragonfly have been reported internationally, including incidents in Norway, Sweden, Denmark, and the United States [2]. Overdose incidents have been recorded in Finland and the United Kingdom as well. Some among these incidents are attributable to mislabeling of Bromo-Dragonfly as its close but significantly less potent phenethylamine relative 2C-B-FLY. Additionally, samples identified as mislabeled were characterized by impurities concerning synthesis; with such a potent compound, the purity of samples becomes extremely significant in judging the activity, and potential for side-effects, even from correctly-measured doses.

Tainted 2C-B-FLY: a fatal trip in San Jose, Cali
Another Bromo-Dragonfly Disaster
GHB not responsible for 18 year olds death (Dragonfly)
2C-B-FLY deaths attributed to Bromo-Dragonfly
Bromo-Dragonfly Death and Hospitalization in Sweden
Denmark: Police warn against dangerous drug (Another Bromo-Dragonfly incident)

These are the dangers common to all psychedelic drugs:

Accidental injury. When on a psychedelic drug, it is easier to accidentally injure yourself. Also because of the disorientating and potentially delusion inspiring nature of the experience, you could be lead to inflict harm on others or yourself. People have fallen off rooftops, run into traffic, attempted to throw people off rooftops as 'sacrifices', drowned, and so on. The best way of protecting against this is to have a friend with you who is sober to look after you and handle any negative situation that might arise.

Bad trips. A bad trip is a negative psychedelic experience. It can range from a mildly negative feeling of anxiety/discomfort, to full-blown psychosis. Bad trips usually ruin a psychedelic experience for the tripper and everyone else. Most bad trips are manageable, just very uncomfortable and difficult. Some are extreme and unmanageable though. It's not uncommon for a bad trip to result in lingering psychological issues. Usually just a few days of negative emotions and anxiety. Sometimes, however, a week or so of serious anxiety, destabilized mental state and impaired functioning is possible. On very rare occasions, a month or two of severely diminished functioning, traumatized mental state, depression & crippling anxiety can occur. More information on bad trips can be found here. The best way of avoiding a bad trip is having the correct set and setting.

Permanent psychosis. Psychedelics are believed by researchers not to cause permanent psychosis, however they could trigger a latent mental illness in someone who was already predisposed to it, or make existing mental illnesses worse. If there is a history of mental illness in your family, you are more likely to be predisposed. Everyone is at some risk, however.

PTSD, anxiety disorder, depression & depersonalization. There are anecdotal reports of the trauma inflicted by some bad trips leading to depression and anxiety which while usually temporary, could potentially develop into lasting disorders. While no different to the potential of any traumatic event to cause lasting disorders, nonetheless this is a danger of psychedelic drug use.

Cardiovascular

Due to both adrenergic and serotonergic activity, the risk of cardiovascular toxicity is quite high - particularly given the ease of overdose when measuring doses of the compound.

Overdose

The risk of overdose concerning this compound is a matter of record, including fatalities attributable to overdoses of the compound without any other drug present upon autopsy [4]. Relevant reports include Swedish hospital records describing a patient characterized as convulsing with respiratory problems, liver and kidney failure, and amputation of several fingers and toes due to necrosis subsequent to oral administration of an unknown dose of Bromo-Dragonfly [2]. The symptoms of severe vasoconstrictive complications may not be apparent for several days after the substance was consumed. Rumors suggest the overdose was due to an administration technique characterized by licking the tip of a finger, and ingesting a sample of the compound that adhered upon exposure. After treatment with 5 mg diazepam (IV) and norepinephrine (IV), the individual additionally suffered from respiratory and metabolic acidosis, successfully treated with assisted respiration and fluid replacement. Over the course of a few days, the individual additionally developed acute liver and renal failure; the individual’s kidneys responded favorably to treatment over the course of three weeks.

Image of necrosis observed in Swedish patient[8]:

Chemical Characteristics

IUPAC: 1-(8-Bromobenzo[1,2-b;4,5-b]difuran-4-yl)-2-aminopropane
Alternative Name: Bromo-Benzodifuranyl-Isopropylamine
CAS#: 502759-67-3 (no record aside from wikipedia)
PubChem#: 10544447 [2]
Molecular Formula: C13H12BrNO2 [2]
Molecular Weight: 294.14388 g/mol [2]
Melting Point: Decomposition at 240˚C (materials at 25˚C)
The compound is chiral, and R-(-)-bromo-DragonFLY is reported to be the more active isomer

Nomenclature and structures for FLYs and dragonFLYs

GC/MS Chromatogram & Mass Spec.

[4]

HPLC Chromatogram & UV-vis Spectra

[4]

1H & 13C NMR Spectra

[4]

Appearance

[2]

Producing Bromo-Dragonfly

<to be completed>

Legal status of Bromo-Dragonfly

Denmark

Controlled substance
Bromo Dragonfly Outlawed Today

Sweden

Controlled Substance

Norway

Controlled Substance

Finland

Bromo-Dragonfly was listed as a narcotic drug without medicinal value late 2012.

Romania

Listed as illegal under 143/2000 as of Feb. 10, 2010 [1]

Potential for Identification as an Analogue (U.S. & Europe)

The structure of Bromo-Dragonfly is quite similar to 2C-B and DOB - both of which are controlled substances in the United States and Europe - rendering the substance likely prosecutable[2].

Bromo-Dragonfly History

Haupt-RC Incident

If you have ordered 2C-B-fly from Haupt-RC, then your life may be in danger
Haupt-RC Distributes Lethal 2C-B-FLY
A Fatal Poisoning Involving Bromo-Dragonfly
If you have ordered 2C-B-fly from Haupt-RC, then your life may be in danger
What lessons can the RC community learn from the Haupt incident?

At least two fatalities and several hospitalizations were reported in October 2009 following the distribution of a batch of Bromo-Dragonfly that was improperly labelled as its far less potent phenethylamine relative, 2C-B-FLY. As the active dose of 2C-B-FLY is in the 10-20mg range, users consuming this batch were consuming a massively toxic overdose of Bromo-DragonFLY. Below are images relevant to the incident.

Image of mislabeled sample, labelled as batch 'b1':

A thin layer chromatography-Marquis assay on the substance linked to these fatalities ruled out the presence of 2C-B-FLY and strongly supported the presence of a psychedelic amphetamine, most likely Bromo-DragonFLY:

(analysis performed by Energy Control, Spain)

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References (need to be formalized)

1. Wikipedia for legal stuff
2. Bromodragonfly report: Psychonaut Web Mapping Project
3. Delayed onset of seizures and toxicity associated with recreational use of Bromo-dragonFLY.
4. A fatal poisoning involving Bromo-Dragonfly.
5. Bowen et. al., 1983 [2]
6. Enantiospecific Synthesis and Pharmacological Evaluation of a Series of Super-Potent, Conformationally Restricted 5-HT2A/2C Receptor Agonists
7. A Novel (benzodifuranyl)aminoalkane with Extremely Potent Activity at the 5-HT2A Receptor
8. http://www.lakartidningen.se/index.p...articleId=9254