2CB7

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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.[1][2][3][4] 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.[1][2][3][4]

The compound has syn and anti stereoisomers, with these isomers also being racemic mixtures of (+)- and (–)- enantiomers.[1][2][3][4] 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.[1][2][3][4] These affinities were dramatically lower than those of 2C-B (Ki = 0.66–0.88 nM).[1][2][3][4]

2CB7 was first described in the scientific literature by Michael Robert Braden and David E. Nichols and colleagues in 2006.[1][2][3][4] It was developed as part of scientific research into serotonin 5-HT2A receptor ligand interactions.[3][4]

See also

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References

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  1. ^ a b c d e f 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. ^ a b c d e f 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. ^ a b c d e f g 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. ^ a b c d e f g 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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