DMBMPP

{{Short description|Chemical compound}}

{{Infobox drug

| image = SS9b_structure.png

| width = 220px

| tradename =

| legal_status =

| class = Selective serotonin 5-HT_2A receptor agonist; Serotonergic psychedelic; Hallucinogen

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 1391499-52-7

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 7H5TDL9Y6X

| ATC_prefix = None

| ATC_suffix =

| PubChem = 72683323

| ChemSpiderID = 59718542

| synonyms = Juncosamine; 2-(2,5-Dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine

| IUPAC_name = 2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine

| C=21 | H=26 | N=1 | O=3 | Br=1

| SMILES = COC(C=C(Br)C(OC)=C1)=C1C[C@@H]2CCC[C@@H](C3=C(OC)C=CC=C3)N2

| StdInChI = 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

| StdInChIKey = KMVGLBONODPTDY-YJBOKZPZSA-N

}}

DMBMPP, or 2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine, also known as juncosamine, is a highly selective serotonin 5-HT_2A receptor agonist and 2-benzylpiperidine analogue of the serotonergic psychedelic 25B-NBOMe that was discovered in 2011 by Jose Juncosa in the group of David E. Nichols at Purdue University.{{cite thesis | first = Jose I. | last = Juncosa | name-list-style = vanc | title=Organic synthesis combined with molecular modeling: A powerful approach to map the functional topography of dopamine and serotonin receptors | url = https://docs.lib.purdue.edu/dissertations/AAI10159203/ | degree = Ph.D. |publisher=Purdue University |date=2011-05-07}}{{cite journal | vauthors = Juncosa JI, Hansen M, Bonner LA, Cueva JP, Maglathlin R, McCorvy JD, Marona-Lewicka D, Lill MA, Nichols DE | title = Extensive rigid analogue design maps the binding conformation of potent N-benzylphenethylamine 5-HT2A serotonin receptor agonist ligands | journal = ACS Chemical Neuroscience | volume = 4 | issue = 1 | pages = 96–109 | date = January 2013 | pmid = 23336049 | pmc = 3547484 | doi = 10.1021/cn3000668 }} It 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.

Despite its uniquely high selectivity for the serotonin 5-HT_2A 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.{{cite journal | vauthors = Märcher Rørsted E, Jensen AA, Kristensen JL | title = 25CN-NBOH: A Selective Agonist for in vitro and in vivo Investigations of the Serotonin 2A Receptor | journal = ChemMedChem | volume = 16 | issue = 21 | pages = 3263–3270 | date = November 2021 | pmid = 34288515 | doi = 10.1002/cmdc.202100395 | url = }} Consequently, 25CN-NBOH, another highly selective serotonin 5-HT_2A receptor agonist, has been proposed as an alternative to DMBMPP for use in scientific research.