2-(2,5-Dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine

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2-(2,5-Dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine
SS9b structure.png
Systematic (IUPAC) name
2-(2,5-Dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine
Clinical data
Legal status
  • Uncontrolled
Identifiers
CAS number 1391499-52-7 N
ATC code ?
Chemical data
Formula C21H26BrNO3 
Mol. mass 420.34 g/mol

2-(2,5-Dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine is an analog of the hallucinogenic N-benzylphenethylamine 25B-NBOMe and was discovered in 2011 by Jose Juncosa in the group of David E. Nichols at Purdue University.[1][2] 2-(2,5-Dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine differs from 25B-NBOMe by having a piperidine ring conformed to the amine, making for a more rigid molecular structure than that of the open-chain 25B-NBOMe. The presence of the piperidine ring introduces two stereocenters, thus, four stereoisomers of this compound can be made. The (S,S)-isomer is the most interesting scientifically as it is the most selective agonist ligand for the human 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 similar 5-HT2C-receptor. Together with 25CN-NBOH,[3] 2-(2,5-Dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine is the only 5-HT2A agonist to exhibit this level of selectivity.


See also[edit]

References[edit]

  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: 120717095020003. doi:10.1021/cn3000668.  edit
  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: 140107104401000. doi:10.1021/cn400216u.  edit