DMBMPP

In today's world, DMBMPP has become a topic of increasing interest to a large number of people. Since its emergence, DMBMPP has generated debates, discussions and reflections in various areas. Regardless of age, gender or educational background, DMBMPP has managed to capture the attention of audiences around the world. Its impact is not limited to a single context, but extends to multiple fields, influencing the way people think, act, and relate to each other. In this article, we will explore in detail the DMBMPP phenomenon and the effects it has had on our society.
DMBMPP
Clinical data
Other namesJuncosamine
ATC code
  • None
Identifiers
  • 2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC21H26BrNO3
Molar mass420.347 g·mol−1
3D model (JSmol)
  • COC(C=C(Br)C(OC)=C1)=C1C2CCC(C3=C(OC)C=CC=C3)N2
  • InChI=1S/C21H26BrNO3/c1-24-19-10-5-4-8-16(19)18-9-6-7-15(23-18)11-14-12-21(26-3)17(22)13-20(14)25-2/h4-5,8,10,12-13,15,18,23H,6-7,9,11H2,1-3H3/t15-,18-/m0/s1
  • Key:KMVGLBONODPTDY-YJBOKZPZSA-N

DMBMPP, or 2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine, is a 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] DMBMPP differs from 25B-NBOMe by incorporating the amine within a piperidine ring, 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 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.[2] Together with 25CN-NBOH,[3] (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)
ketanserin 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. ^ Juncosa JI (2011-05-07). Organic synthesis combined with molecular modeling: A powerful approach to map the functional topography of dopamine and serotonin receptors (Ph.D. thesis). Purdue University.
  2. ^ a b Juncosa JI, Hansen M, Bonner LA, Cueva JP, Maglathlin R, McCorvy JD, Marona-Lewicka D, Lill MA, Nichols DE (January 2013). "Extensive rigid analogue design maps the binding conformation of potent N-benzylphenethylamine 5-HT2A serotonin receptor agonist ligands". ACS Chemical Neuroscience. 4 (1): 96–109. doi:10.1021/cn3000668. PMC 3547484. PMID 23336049.
  3. ^ Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, Kristensen JL (March 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.
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