DMBMPP, also known as juncosamine or as 2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine, is a highly selective serotonin 5-HT2A receptor agonist and 2-benzylpiperidine analogue of the serotonergic psychedelic 25B-NBOMe which is used in scientific research.
Interactions
Pharmacology Pharmacodynamics The (S,S)-isomer ((2S,6S)-DMBMPP) is the most selective agonist for the human serotonin 5-HT2A receptor yet discovered, with a affinity (Ki) of 2.5nM at the human serotonin 5-HT2A receptor and with 124-fold selectivity for the serotonin 5-HT2A receptor over the structurally similar serotonin 5-HT2C receptor. Together with 25CN-NBOH, (2S,6S)-DMBMPP is the only known 5-HT2A agonist to exhibit this level of selectivity. In contrast to the case of the serotonin 5-HT2A receptor, no functional data has been reported for DMBMPP at the serotonin 5-HT2C receptor as of 2023.
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
(S,S)-DMBMPP was assessed and found to fully substitute for the psychedelic drug LSD in rodent drug discrimination tests. As such, DMBMPP may be expected to have hallucinogenic effects in humans.
Despite its uniquely high selectivity for the serotonin 5-HT2A receptor, it has been said that DMBMPP is not widely used as a pharmacological tool in scientific research, presumably due to its chemical synthesis being relatively inaccessible. Consequently, 25CN-NBOH, another highly selective serotonin 5-HT2A receptor agonist, has been proposed as an alternative to DMBMPP for use in scientific research. DMBMPP and 25CN-NBOH are the two most selective serotonin 5-HT2A receptor agonists known as of 2020.
Chemistry DMBMPP, also known as 2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine, is a cyclized phenethylamine, 2C, and NBOMe derivative of 2C-B and 25B-NBOMe. It differs from 25B-NBOMe by incorporating the amine within a piperidine ring, making for a more conformationally restrained, 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.
History DMBMPP was first described in the scientific literature by Jose Juncosa of the lab of David E. Nichols at Purdue University in 2011.
Society and culture Legal status Canada DMBMPP is not an explicitly controlled substance in Canada as of 2025. However, it might be covered under phenethylamine and amphetamine blanket-ban language, although this is unclear due to its nature as a cyclized phenethylamine.
United States DMBMPP is not an explicitly controlled substance in the United States. However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.
See also Cyclized phenethylamine Substituted 2-benzylpiperidine 25CN-NBOH DOB-NBOMe Z3517967757 2C-B-3PIP LPH-5 TGF-8027
References
External links DMBMPP - Isomer Design