|Chemical and physical data|
|Molar mass||420.34 g/mol g·mol−1|
|3D model (JSmol)|
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. 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.
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. Together with 25CN-NBOH, 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|
|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|
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