Chemistry:2CB7

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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

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 (in de) Phenethylamine: von der Struktur zur Funktion. Nachtschatten-Science (1 ed.). Solothurn: Nachtschatten-Verlag. 2013. pp. 848–849. ISBN 978-3-03788-700-4. OCLC 858805226. https://books.google.com/books?id=-Us1kgEACAAJ. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chemical Reviews 124 (1): 124–163. January 2024. 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. ↑ 3.0 3.1 3.2 3.3 3.4 3.5 3.6 "1-Aminomethylbenzocycloalkanes: conformationally restricted hallucinogenic phenethylamine analogues as functionally selective 5-HT2A receptor agonists". Journal of Medicinal Chemistry 49 (19): 5794–5803. September 2006. doi:10.1021/jm060656o. PMID 16970404. 
  4. ↑ 4.0 4.1 4.2 4.3 4.4 4.5 4.6 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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