DMBMPP

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] 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.

DMBMPP
Clinical data
Other namesJuncosamine
ATC code
  • None
Identifiers
IUPAC name
  • 2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC21H26BrNO3
Molar mass420.347 g·mol−1
3D model (JSmol)
SMILES
  • COC(C=C(Br)C(OC)=C1)=C1C[C@@H]2CCC[C@@H](C3=C(OC)C=CC=C3)N2
InChI
  • 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

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.

LigandKi ± SEM (nM)Ki ± SEM (nM)Ki ± SEM (nM)
[3H] ketanserin[3H] mesulerginefold selectivity
h5-HT2Ah5-HT2Ch5-HT2C/h5-HT2A
2C-B6.0 ± 0.323.8 ± 2.69.5
25B-NBOMe0.19 ± 0.014.0 ± 0.421
(±)-DMBMPP5.3 ± 0.3520 ± 2298
(S,S)-(−)-DMBMPP2.5 ± 0.1310 ± 42124
(R,R)-(+)-DMBMPP2,100 ± 17128,600 ± 470027

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. 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. 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.
  4. 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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