2C-B-DRAGONFLY

Last updated
2C-B-DRAGONFLY
2CB-DRAGONFLY structure.png
Legal status
Legal status
  • UK:In general Unscheduled
Identifiers
  • 2-(4-bromofuro[2,3-f][1]benzofuran-8-yl)ethanamine
CAS Number
PubChem CID
Chemical and physical data
Formula C12H10BrNO2
Molar mass 280.121 g·mol−1
3D model (JSmol)
  • C1=COC2=C(C3=C(C(=C21)CCN)OC=C3)Br
  • InChI=1S/C12H10BrNO2/c13-10-9-3-6-15-11(9)7(1-4-14)8-2-5-16-12(8)10/h2-3,5-6H,1,4,14H2
  • Key:JWBRIUSZWWDKGO-UHFFFAOYSA-N

2C-B-DRAGONFLY (2C-B-DFLY) is a recreational designer drug with psychedelic effects. It can be regarded as the fully aromatic derivative of 2C-B-FLY. 2C-B-DRAGONFLY is stronger than 2C-B or 2C-B-FLY with around 2-3x the potency of 2C-B in animal studies, demonstrating the importance of the fully aromatic benzodifuran ring system for optimum receptor binding at 5-HT2A, but it is still considerably less potent than its alpha-methyl derivative Bromo-DragonFLY. [1] [2]

See also

Related Research Articles

<span class="mw-page-title-main">2C-B</span> Chemical compound

2C-B (4-Bromo-2,5-dimethoxyphenethylamine) is a synthetic psychedelic drug of the 2C family, commonly used as a recreational drug. Initially synthesized by Alexander Shulgin in 1974, to date, the substance has limited scientific information regarding its pharmacological effects and pharmacokinetics on humans. The existing studies primarily classify 2C-B as a stimulant, and hallucinogen, and less commonly as an entactogen, and empathogen.

<span class="mw-page-title-main">Bromo-DragonFLY</span> Chemical compound

Bromo-DragonFLY is a substance related to the phenethylamine family. It acts as a potent full agonist for the 5-HT2A receptor.

<span class="mw-page-title-main">2C-B-FLY</span> Psychedelic designer drug

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

<span class="mw-page-title-main">25I-NBOH</span> Chemical compound

25I-NBOH is a derivative of the phenethylamine-derived hallucinogen 2C-I that was discovered in 2006 by a team at Purdue University.

<span class="mw-page-title-main">2CBCB-NBOMe</span> Chemical compound

2CBCB-NBOMe (NBOMe-TCB-2) is a compound indirectly derived from the phenethylamine series of hallucinogens, which was discovered in 2007 at Purdue University as part of the ongoing research program of the team led by David Nichols focusing on the mapping of the specific amino acid residues responsible for ligand binding to the 5HT2A receptor. 2CBCB-NBOMe acts as a potent and selective agonist for the 5-HT2A and 5-HT2C receptors, with a Ki of 0.27 nM at the human 5-HT2A receptor, a similar potency to other agonists such as TCB-2, NBOMe-2C-I and Bromo-DragonFLY.

<span class="mw-page-title-main">2CBFly-NBOMe</span> Chemical compound

2CBFly-NBOMe is a compound indirectly derived from the phenethylamine hallucinogen 2C-B, and related to benzodifurans like 2C-B-FLY and N-benzylphenethylamines like 25I-NBOMe. It was discovered in 2002, and further researched by Ralf Heim at the Free University of Berlin, and subsequently investigated in more detail by a team at Purdue University led by David E. Nichols. It acts as a potent partial agonist for the 5HT2A serotonin receptor subtype.

<span class="mw-page-title-main">TFMFly</span> Chemical compound

TFMFly is a compound related to psychedelic phenethylamines such as 2C-B-FLY and 2C-TFM. It was first reported in 2005 by a team at Purdue University led by David Nichols. It acts as a potent agonist at the 5HT2A serotonin receptor subtype, and is a chiral compound with the more active (R) enantiomer having a Ki of 0.12 nM at the human 5HT2A receptor. While the fully aromatic benzodifurans such as Bromo-DragonFLY generally have higher binding affinity than saturated compounds like 2C-B-FLY, the saturated compounds have higher efficacy as agonists.

<span class="mw-page-title-main">25B-NBOMe</span> Chemical compound

25B-NBOMe is a derivative of the phenethylamine psychedelic 2C-B, discovered in 2004 by Ralf Heim at the Free University of Berlin. It acts as a potent full agonist for the 5HT2A receptor. Anecdotal reports from users suggest 25B-NBOMe to be an active hallucinogen at a dose of as little as 250–500 µg, making it a similar potency to other phenethylamine derived hallucinogens such as Bromo-DragonFLY. Duration of effects lasts about 12–16 hours, although the parent compound is rapidly cleared from the blood when used in the radiolabeled form in tracer doses. Recently, Custodio et al (2019) evaluated the potential involvement of dysregulated dopaminergic system, neuroadaptation, and brain wave changes which may contribute to the rewarding and reinforcing properties of 25B-NBOMe in rodents.

<span class="mw-page-title-main">2CB-Ind</span> Chemical compound

2CB-Ind is a conformationally-restricted derivative of the phenethylamine hallucinogen 2C-B, discovered in 1974 by Alexander Shulgin. It acts as a moderately potent and selective agonist for the 5-HT2A and 5-HT2C receptors, but unlike the corresponding benzocyclobutene derivative TCB-2 which is considerably more potent than the parent compound 2C-B, 2CB-Ind is several times weaker, with racemic 2CB-Ind having a Ki of 47nM at the human 5-HT2A receptor, only slightly more potent than the mescaline analogue (R)-jimscaline.

<span class="mw-page-title-main">25D-NBOMe</span> Chemical compound

25D-NBOMe is a derivative of the phenethylamine derived hallucinogen 2C-D. It acts in a similar manner to related compounds such as 25I-NBOMe, which is a potent agonist at the 5HT2A receptor. 25D-NBOMe has been sold as a street drug since 2010 and produces similar effects in humans to related compounds such as 25I-NBOMe and 25C-NBOMe. It was banned as a Temporary Class Drug in the UK on 10 June 2013 after concerns about its recreational use.

<span class="mw-page-title-main">25C-NBOH</span> Chemical compound

25-C-NBOH is a derivative of the phenethylamine derived hallucinogen 2C-C which has been sold as a designer drug. It has similar serotonin receptor affinity to the better-known compound 25C-NBOMe.

<span class="mw-page-title-main">25E-NBOMe</span> Chemical compound

25E-NBOMe is a derivative of the phenethylamine 2C-E. It acts in a similar manner to related compounds such as 25I-NBOMe, which are potent agonists at the 5HT2A receptor. 25E-NBOMe has been sold as a drug and produces similar effects in humans to related compounds such as 25I-NBOMe and 25C-NBOMe.

<span class="mw-page-title-main">25B-NBOH</span> Chemical compound

25B-NBOH is a derivative of the phenethylamine derived hallucinogen 2C-B which has been sold as a designer drug. It acts as a potent serotonin receptor agonist with similar affinity to the better-known compound 25B-NBOMe at 5-HT2A and 5-HT2C receptors with pKis values of 8.3 and 9.4, respectively.

<i>alpha</i>-Pyrrolidinopentiothiophenone Chemical compound

α-Pyrro​lidino​pentio​thiophenone is a synthetic stimulant of the cathinone class that has been sold online as a designer drug. It is an analogue of α-PVP where the phenyl ring has been replaced by thiophene.

<span class="mw-page-title-main">2C-B-BUTTERFLY</span> Chemical compound

2C-B-BUTTERFLY is a conformationally-restricted derivative of the phenethylamine hallucinogen 2C-B, which was discovered in 1999 by Michael S. Whiteside and Aaron Monte. It is a ring-expanded homologue of the better known compound 2C-B-FLY, and has similar properties as an agonist for serotonin receptors, but with more selectivity for 5-HT2C over 5-HT2A.

<span class="mw-page-title-main">Substituted benzofuran</span> Class of chemical compounds

The substituted benzofurans are a class of chemical compounds based on the heterocyclyc and polycyclic compound benzofuran. Many medicines use the benzofuran core as a scaffold, but most commonly the term is used to refer to the simpler compounds in this class which include numerous psychoactive drugs, including stimulants, psychedelics and empathogens. In general, these compounds have a benzofuran core to which a 2-aminoethyl group is attached, and combined with a range of other substituents. Some psychoactive derivatives from this family have been sold under the name Benzofury.

<span class="mw-page-title-main">25B-NBF</span> Chemical compound

25B-NBF is a derivative of the phenethylamine hallucinogen 2C-B, which acts as a highly potent partial agonist for the human 5-HT2A receptor.

<span class="mw-page-title-main">DOB-FLY</span> Psychedelic designer drug

DOB-FLY is a recreational designer drug with psychedelic effects. It can be regarded as the alpha-methyl derivative of 2C-B-FLY or the partially saturated counterpart of bromo-dragonfly. Unlike bromo-dragonfly, DOB-FLY is only slightly more potent than DOB itself, with an active dose in humans of around 1 mg.

<span class="mw-page-title-main">2C-E-FLY</span> Chemical compound

2C-E-FLY is a recreational designer drug with psychedelic effects. It is slightly less potent than 2C-E or 2C-B-FLY in animal studies but retains drug-appropriate responding.

<span class="mw-page-title-main">25T7-NBOMe</span> Chemical compound

25T7-NBOMe is a substituted phenethylamine derivative from the 25-NB family. It acts as an agonist at the 5-HT2A and 5-HT2C serotonin receptors, has psychedelic effects and has been sold as a designer drug.

References

  1. Zaitsu K, Katagi M, Kamata H, Nakanishi K, Shima N, Kamata T, et al. (January 2010). "Simultaneous analysis of six novel hallucinogenic (tetrahydrobenzodifuranyl) aminoalkanes (FLYs) and (benzodifuranyl) aminoalkanes (DragonFLYs) by GC-MS, LC-MS, and LC-MS-MS". Forensic Toxicology. 28 (1): 9–18. doi:10.1007/s11419-009-0083-0. S2CID   24100422.
  2. Halberstadt AL, Chatha M, Stratford A, Grill M, Brandt SD (January 2019). "Comparison of the behavioral responses induced by phenylalkylamine hallucinogens and their tetrahydrobenzodifuran ("FLY") and benzodifuran ("DragonFLY") analogs". Neuropharmacology. 144: 368–376. doi:10.1016/j.neuropharm.2018.10.037. PMC   6863604 . PMID   30385253.