DMBMPP


DMBMPP, or 2--6-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.

Pharmacology

The -isomer 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.
LigandKi ± SEM Ki ± SEM Ki ± SEM
ketanserin 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
--DMBMPP2.5 ± 0.1310 ± 42124
--DMBMPP2,100 ± 17128,600 ± 470027