DMBMPP

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by Forever elementary student (talk | contribs) at 04:05, 16 October 2016. The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

DMBMPP
Clinical data
ATC code
  • None
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • 2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine
CAS Number
PubChem CID
Chemical and physical data
FormulaC21H26BrNO3
Molar mass420.34 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

DMBMPP, or 2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine, is an 2-Benzylpiperidine 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] DMBPP 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.

Pharmacology

The (S,S)-isomer (2S,6S-DMBMPP) is the most interesting scientifically as it is the most selective agonist 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.[3] Together with 25CN-NBOH,[4] 2S,6S-DMBMPP is the only known 5-HT2A agonist to exhibit this level of selectivity.

Ligand Ki ± SEM (nM) Ki ± SEM (nM) Ki ± SEM (nM)
[3H] ketanserin [3H] mesulergine fold selectivity
h5-HT2A h5-HT2C h5-HT2C/h5-HT2A
2C-B 6.0 ± 0.3 23.8 ± 2.6 9.5
25B-NBOMe 0.19 ± 0.01 4.0 ± 0.4 21
(±)-DMBMPP 5.3 ± 0.3 520 ± 22 98
(S,S)-(−)-DMBMPP 2.5 ± 0.1 310 ± 42 124
(R,R)-(+)-DMBMPP 2,100 ± 171 28,600 ± 4700 27

See also

References

  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.
  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.
  3. ^ http://pubs.acs.org/doi/abs/10.1021/cn3000668
  4. ^ 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.