2C-B-FLY

2C-B-FLY is a psychedelic and designer drug of the phenethylamine, 2C, and FLY families. It was first synthesized in 1996 by Aaron Monte, Professor of Chemistry at UW-La Crosse.^[1][2]

2C-B-FLY

Clinical data
Routes of administration	Oral
Drug class	Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act
Identifiers
IUPAC name 2-(4-Bromo-2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-8-yl)ethanamine
CAS Number	733720-95-1 Y
PubChem CID	10265873
ChemSpider	8441352
UNII	Z1T18Z40OT
ChEMBL	ChEMBL101189
CompTox Dashboard (EPA)	DTXSID301342541 DTXSID00170510, DTXSID301342541
Chemical and physical data
Formula	C12H14BrNO2
Molar mass	284.153 g·mol−1
3D model (JSmol)	Interactive image
Melting point	310 °C (590 °F)
SMILES NCCc1c2CCOc2c(Br)c3CCOc13
InChI InChI=1S/C12H14BrNO2/c13-10-9-3-6-15-11(9)7(1-4-14)8-2-5-16-12(8)10/h1-6,14H2 Y Key:YZDFADGMVOSVIX-UHFFFAOYSA-N Y

This molecule was researched by Alexander Shulgin, and it was Ann Shulgin's favorite research chemical.^[3][4]

Chemistry

2C-B-Fly in powder form

2C-B-FLY is 8-bromo-2,3,6,7-benzo-dihydro-difuran-ethylamine. The full name of the chemical is 2-(8-bromo-2,3,6,7-tetrahydrofuro[2,3-f] [1]benzofuran-4-yl)ethanamine. It has been subject of little formal study, but its appearance as a designer drug has led the DEA to release analytical results for 2C-B-FLY and several related compounds.

Analogs and derivatives

Analogues and derivatives of 2C-B:

25-N:

• 25B-N1POMe
• 25B-NAcPip

25-NB:

• 25B-NB
• 25B-NB23DM
• 25B-NB25DM
• 25B-NB3OMe
• 25B-NB4OMe
• 25B-NBF
• 25B-NBMD
• 25B-NBOH
• 25B-NBOMe (NBOMe-2CB)
  • DMBMPP

25-NM:

• 25B-NMe7BF
• 25B-NMe7BT
• 25B-NMe7Bim
• 25B-NMe7Box
• 25B-NMe7DHBF
• 25B-NMe7Ind
• 25B-NMe7Indz
• 25B-NMePyr

Substituted benzofurans:

• 2C-B-FLY
  • 2C-B-BUTTERFLY
  • 2C-B-DRAGONFLY
• 2CBFly-NBOMe (NBOMe-2CB-Fly)
• DOB-FLY
• DOB-2-DRAGONFLY-5-BUTTERFLY

N-(2C)-fentanyl:

• N-(2C-B) fentanyl^[5]
  • N-(2C-B-FLY) fentanyl^[6]

Other:

• BOB
• BOH-2C-B, β-Hydroxy-2C-B, βOH-2CB^[7][8]
• BMB
• 2C-B-5-hemifly
• 2C-B-aminorex (2C-B-AR)
• 2C-B-AN
• 2C-B-BZP
• 2C-B-FLY-NB2EtO5Cl
• 2C-B-PP
• 2CB-Ind
• βk-2C-B (beta-keto 2C-B)
• N-Ethyl-2C-B
• TCB-2 (2C-BCB)

In theory, dihydro-difuran analogs of any of the 2Cx / DOx family of drugs could be made, and would be expected to show similar activity to the parent compounds, 2-CB, DOB, DOM, etc. In the same way that 2C-B-FLY is the dihydro-difuran analog of 2C-B, the 8-iodo equivalent, "2C-I-FLY," would be the dihydro-difuran analogue of 2C-I, and the 8-methyl equivalent, "2C-D-FLY," would be the dihydro-difuran analogue of 2C-D.

Other related compounds can also be imagined and produced in which the alpha carbon of the ethylamine sidechain is methylated, giving the amphetamine derivative DOB-FLY, with this compound being the dihydro-difuran analogue of DOB, which can be viewed as the fully unsaturated derivative of Bromo-DragonFLY.

When only one methoxy group of a 2Cx drug is cyclized into a dihydro-furan ring, the resulting compound is known as a "hemifly", (and these could be termed 2- or 5- "hemis," depending on where the single dihydro-furan ring is placed). And when an unsaturated furan ring is inserted, the compound is known as a "hemi-dragonfly". The larger, fully saturated, hexahydro-benzo-dipyran ring derivative has been referred to as "2C-B-MOTH." The 8-bromo group can also be replaced by other groups to produce compounds such as TFMFly.

A large number of symmetrical and asymmetrical derivatives can be produced by using different combinations of ring systems. Because the 2- and 5- positions (using the common phenylethylamine numbering scheme), the 2- and 5-positions of the benzene ring, if named as benzo-difurans are not equivalent.^{[clarification needed]} Asymmetrical combinations have two possible positional isomers, with different pharmacological activities, at the various 5-HT₂ subtypes. These compounds were casually referred to as the "2C-B-GNAT," and "2C-B-FLEA" compounds, which contain 5 or 6 membered rings at the 2- vs. 5-positions, respectively. Isomeric "Ψ"-derivatives with the oxygens positioned at the 2,6- positions, and mescaline analogues with the oxygens at 3,5- have also been made, but both are less potent than the corresponding 2,5- isomers.^[9][10] The symmetrical aromatic benzodifuran derivatives tend to have the highest binding affinity at 5-HT_2A, but the saturated benzodifuran derivatives have higher efficacy, while the saturated benzodipyran derivatives are more selective for 5-HT_2C. A large number of possible combinations have been synthesised and tested for activity, but these represent only a fraction of the many variations that could be produced.^{[11][12][13][14][15][16][17][18][19][20][21]}

2C-BFLY and some selected analogues (SAR)

Dosage

Alexander Shulgin lists a dosage of 2C-B-FLY from 10 to 20 mg orally.^{[citation needed]}

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Toxicity

The toxicity of 2C-B-FLY in humans is unknown. Two deaths occurred in October 2009, in Denmark and the United States, after ingestion of a substance that was sold as 2C-B-FLY in a small-time RC shop, but in fact consisted of Bromo-DragonFLY contaminated with a small amount of unidentified impurities.^[22]

Pharmacology

2C-B-FLY activities

Target	Affinity (Ki, nM)
5-HT1A	147–350
5-HT1B	185
5-HT1D	1.4
5-HT1E	110
5-HT1F	ND
5-HT2A	11–11.6 (Ki) 0.029–53.7 (EC50Tooltip half-maximal effective concentration) 80–104% (EmaxTooltip maximal efficacy)
5-HT2B	0.9 (Ki) 0.123–40 (EC50) 56–108% (Emax)
5-HT2C	10.6–12 (Ki) 0.0615–0.149 (EC50) 100–108% (Emax)
5-HT3	>10,000
5-HT4	ND
5-HT5A	>10,000
5-HT6	150
5-HT7	606
α1A	11,000
α1B	>10,000
α1D	ND
α2A	145–780
α2B	624
α2C	233
β1	>10,000
β2	>10,000
β3	ND
D1	1,400–4,963
D2	1,900–6,835
D3	6,800
D4	>10,000
D5	>10,000
H1	3,400–5,753
H2–H4	>10,000
M1	643
M2	2,029
M3	339
M4	520
M5	873
I1	>10,000
σ1	>10,000
σ2	>10,000
TAAR1Tooltip Trace amine-associated receptor 1	710 (Ki) (mouse) 30 (Ki) (rat) 1,800 (EC50) (mouse) 270 (EC50) (rat) >30,000 (EC50) (human) 49% (Emax) (mouse) 48% (Emax) (rat)
SERTTooltip Serotonin transporter	10,000 (Ki) 73,000 (IC50Tooltip half-maximal inhibitory concentration) (EC50)
NETTooltip Norepinephrine transporter	17,000 (Ki) 97,000 (IC50) (EC50)
DATTooltip Dopamine transporter	>26,000 (Ki) 187,000 (IC50) (EC50)
MAO-ATooltip Monoamine oxidase A	19,000 (IC50)
MAO-BTooltip Monoamine oxidase B	ND (IC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [23][24][25][26][27][28][29][30]

2C-B-FLY is a potent agonist of the serotonin 5-HT₂ receptors, including the serotonin 5-HT_2A, serotonin 5-HT_2B, and serotonin 5-HT_2C receptors.^[25][26] Unusually among 2C drugs, 2C-B-FLY also shows high affinity for the serotonin 5-HT_1D receptor.^[25] It also has relatively weak affinity for the serotonin 5-HT_1A, 5-HT_1B, and 5-HT_1E receptors.^[25][26]

Legality

Canada

As of October 31, 2016; 2C-B-FLY is a controlled substance (Schedule III) in Canada.^[31]

Finland

Scheduled in the "government decree on psychoactive substances banned from the consumer market".^[32]

United States

2C-B-FLY is unscheduled and uncontrolled in the United States. However, it may fall under the scope of the Federal Analog Act if it is intended for human consumption given its similarity to 2C-B.