Article · Wikipedia archive · Last revised Jun 17, 2026

2CB7

2CB7, also known as 2C-B-5-hemiFLY-β7, is a serotonin receptor modulator of the phenethylamine, 2C, and benzofuran families related to 2C-B. It is a cyclized phenethylamine or conformationally restrained derivative of 2C-B in which the 5-methoxy group has been cyclized into a dihydrofuran ring and the β position has been connected with the dihydrofuran ring via a propyl group to form a cycloheptane ring to form a tricyclic structure.

Last revised
Jun 17, 2026
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≈ 2 min
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2CB7
Clinical data
Other names2C-B-5-hemiFLY-β7
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor modulator
ATC code
  • None
Identifiers
  • (5-bromo-7-methoxy-3-oxatricyclo[6.4.1.04,13]trideca-4,6,8(13)-trien-9-yl)methanamine
PubChem CID
ChemSpider
Chemical and physical data
FormulaC14H18BrNO2
Molar mass312.207 g·mol−1
3D model (JSmol)
  • COC1=CC(=C2C3=C1C(CCCC3CO2)CN)Br
  • InChI=1S/C14H18BrNO2/c1-17-11-5-10(15)14-13-9(7-18-14)4-2-3-8(6-16)12(11)13/h5,8-9H,2-4,6-7,16H2,1H3
  • Key:IKKCIFAOANLPEY-UHFFFAOYSA-N

2CB7, also known as 2C-B-5-hemiFLY-β7, is a serotonin receptor modulator of the phenethylamine, 2C, and benzofuran families related to 2C-B.1234 It is a cyclized phenethylamine or conformationally restrained derivative of 2C-B in which the 5-methoxy group has been cyclized into a dihydrofuran ring and the β position has been connected with the dihydrofuran ring via a propyl group to form a cycloheptane ring to form a tricyclic structure.1234

The compound has syn and anti stereoisomers, with these isomers also being racemic mixtures of (+)- and (–)- enantiomers.1234 The isomers of 2CB7 show affinity for the serotonin 5-HT2A receptor, with values (Ki) of 74 to 170 nM for syn-2CB7 and 170 to 200 nM for anti-2CB7.1234 These affinities were dramatically lower than those of 2C-B (Ki = 0.66–0.88 nM).1234

2CB7 was first described in the scientific literature by Michael Robert Braden and David E. Nichols and colleagues in 2006.1234 It was developed as part of scientific research into serotonin 5-HT2A receptor ligand interactions.34

See also

See also

References

References

  1. 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. pp. 848–849. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.
  2. Duan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chemical Reviews. 124 (1): 124–163. doi:10.1021/acs.chemrev.3c00375. PMID 38033123. Cyclopentyl or cycloheptyl compounds, for example, 133, 134, and 135 (Figure 12B), however, showed decreased binding affinity for 5-HT2AR.
  3. McLean TH, Parrish JC, Braden MR, Marona-Lewicka D, Gallardo-Godoy A, Nichols DE (September 2006). "1-Aminomethylbenzocycloalkanes: conformationally restricted hallucinogenic phenethylamine analogues as functionally selective 5-HT2A receptor agonists". Journal of Medicinal Chemistry. 49 (19): 5794–5803. doi:10.1021/jm060656o. PMID 16970404.
  4. Braden MR (2007). Towards a biophysical understanding of hallucinogen action (Ph.D. thesis). Purdue University. ProQuest 304838368. Table 4.7 Effect of the N6.55(343)A mutation on binding to the h5-HT2A receptor. [...] Table 4.8 Effect of the N6.55(343)A mutation on h5-HT2A receptor-mediated PI hydrolysis.
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