Movatterモバイル変換

[0]ホーム
URL:

Jump to content
WikipediaThe Free Encyclopedia
Search

2CB7

From Wikipedia, the free encyclopedia

Pharmaceutical compound
2CB7
Clinical data
Other names2C-B-5-hemiFLY-β7
Drug classSerotonin receptor modulator;Serotonin5-HT2A receptormodulator
ATC code
  • None
Identifiers
  • (5-bromo-7-methoxy-3-oxatricyclo[6.4.1.04,13]trideca-4,6,8(13)-trien-9-yl)methanamine
PubChemCID
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 as2C-B-5-hemiFLY-β7, is aserotonin receptor modulator of thephenethylamine,2C, andbenzofuran families related to2C-B.[1][2][3][4] It is acyclized phenethylamine orconformationally restrainedderivative of 2C-B in which the 5-methoxy group has beencyclized into adihydrofuranring and the β position has been connected with the dihydrofuran ring via apropyl group to form acycloheptane ring to form atricyclicstructure.[1][2][3][4]

The compound hassyn andantistereoisomers, with these isomers also beingracemic mixtures of (+)- and (–)-enantiomers.[1][2][3][4] The isomers of 2CB7 showaffinity for theserotonin5-HT2A receptor, with values (Ki) of 74 to 170 nM forsyn-2CB7 and 170 to 200 nM foranti-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 thescientific literature by Michael Robert Braden andDavid E. Nichols and colleagues in 2006.[1][2][3][4] It was developed as part ofscientific research into serotonin 5-HT2A receptorligand interactions.[3][4]

See also

[edit]

References

[edit]
  1. ^abcdefTrachsel 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 fromthe original on 21 August 2025.
  2. ^abcdefDuan 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. ^abcdefgMcLean 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. ^abcdefgBraden 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.

External links

[edit]
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
Phenethylamines
Amphetamines
Phentermines
Cathinones
Phenylisobutylamines
(and further-extended)
Catecholamines
(and close relatives)
Cyclized
phenethylamines
Phenylalkylpyrrolidines
2-Benzylpiperidines
(phenidates)
Phenylmorpholines
(phenmetrazines)
Phenyloxazolamines
(aminorexes)
Isoquinolines and
tetrahydroisoquinolines
2-Aminoindanes
2-Aminotetralins
Others / unsorted
Related compounds
Retrieved from "https://en.wikipedia.org/w/index.php?title=2CB7&oldid=1321553192"
Categories:
Hidden categories:
[8]ページ先頭
©2009-2025 Movatter.jp