2C-B-DragonFLY

2C-B-DragonFLY
Clinical data
Other names2C-B-DFLY
Drug classSerotonergic psychedelic; Hallucinogen
Legal status
Legal status
  • In general unscheduled
Identifiers
  • 2-(4-bromofuro[2,3-f][1]benzofuran-8-yl)ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC12H10BrNO2
Molar mass280.121 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, also known as 2C-B-DFLY, is a psychedelic drug of the phenethylamine, 2C, and FLY families.[1][2][3] It is the "DragonFLY" (benzodifuran) analogue of 2C-B and 2C-B-FLY as well as the phenethylamine (α-desmethyl) analogue of Bromo-DragonFLY (DOB-DFLY).[1][2]

Use and effects

The properties and effects of 2C-B-DragonFLY in humans do not appear to be known.[4][5]

Interactions

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

Pharmacology

Pharmacodynamics

2C-B-DragonFLY's predicted affinity (Ki) for the serotonin 5-HT2A receptor has been reported to be 26 nM.[3] It produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[1] 2C-B-DragonFLY is about 2.2-fold more potent than 2C-B and about 1.7-fold more potent than 2C-B-FLY in terms of this effect.[1] On the other hand, it is about 5-fold less potent than Bromo-DragonFLY in producing the head-twitch response in rodents.[1] These findings demonstrate the importance of the fully aromatic benzodifuran ring system for optimal serotonin 5-HT2A receptor interaction, though 2C-B-DragonFLY is still considerably less potent than Bromo-DragonFLY.[1]

Chemistry

Analogues

Analogues of 2C-B-DragonFLY include 2C-B, 2C-B-FLY, 2C-B-ButterFLY, and Bromo-DragonFLY (DOB-DFLY), among others.[4][5]

History

2C-B-DragonFLY was first described in the scientific literature by 1999.[3][2][1] Subsequently, its pharmacology was described by Adam Halberstadt and colleagues in 2019.[1]

Society and culture

Canada

2C-B-DragonFLY is a controlled substance in Canada under phenethylamine blanket-ban language.[6]

United States

2C-B-DragonFLY is not an explicitly controlled substance in the United States.[7]

See also

References

  1. ^ a b c d e f g h 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.
  2. ^ a b c 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.
  3. ^ a b c Schulze-Alexandru, Meike; Kovar, Karl-Artur; Vedani, Angelo (1999). "Quasi-atomistic Receptor Surrogates for the 5-HT2A Receptor: A 3D-QSAR Study on Hallucinogenic Substances". Quantitative Structure-Activity Relationships. 18 (6): 548–560. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B. ISSN 0931-8771. Retrieved 8 March 2026.
  4. ^ a b Shulgin, A.; Manning, T.; Daley, P.F. (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
  5. ^ a b Trachsel, D.; Lehmann, D.; Enzensperger, C. (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.
  6. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
  7. ^ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026
allikas: https://en.wikipedia.org/wiki/2C-B-DragonFLY