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User:Pjw154/sandbox

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Pjw154/sandbox
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • (2S,6S)-2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine
CAS Number
Chemical and physical data
FormulaC21H26BrNO3
Molar mass320.34 g/mol g·mol−1
3D model (JSmol)
  • COC(C=C(Br)C(OC)=C1)=C1C[C@@H]2CCC[C@@H](C3=C(OC)C=CC=C3)N2

Juncosamine is a conformationally constrained analogue of the N-benzylphenethylamine 25B-NBOMe and was discovered in 2011 by Jose Juncosa in the group of David E. Nichols at Purdue University[1][2]. The (S,S) isomer of Juncosamine is the most selective agonist ligand for the 5-HT2A receptor yet discovered, with a Ki of 2.5 nM at the human 5-HT2A receptor and with 124-fold selectivity for 5-HT2A over the structurally homologous 5-HT2C-receptor. Together with 25CN-NBOH,[3] Juncosamine is the only 5-HT2A agonist to exhibit this level of selectivity.

See also

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References

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  1. ^ Jose Juncosa (2011-05-07). "Organic synthesis combined with molecular modeling: A powerful approach to map the functional topography of dopamine and serotonin receptors". Purdue University. Retrieved 2014-01-13.
  2. ^ Juncosa, J. I.; Hansen, M.; Bonner, L. A.; Cueva, J. P.; Maglathlin, R.; McCorvy, J. D.; Marona-Lewicka, D.; Lill, M. A.; Nichols, D. E. (2012). "Extensive rigid analogue design maps the binding conformation of potent N-benzylphenethylamine 5-HT2A serotonin receptor agonist ligands". ACS Chemical Neuroscience. 4: 96–109. doi:10.1021/cn3000668. PMC 3547484. PMID 23336049.
  3. ^ Hansen, M.; Phonekeo, K.; Paine, J. S.; Leth-Petersen, S.; Begtrup, M.; Bräuner-Osborne, H.; Kristensen, J. L. (2014). "Synthesis and Structure-Activity Relationships of N-Benzyl Phenethylamines as 5-HT2A/2C Agonists". ACS Chemical Neuroscience. 5 (3): 243–9. doi:10.1021/cn400216u. PMC 3963123. PMID 24397362.


Category:2C (psychedelics) Category:5-HT2A agonists Category:5-HT2C agonists