| Iupac Name: | 2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine |
| Width: | 220 |
| Cas Number: | 1391499-52-7 |
| Atc Prefix: | None |
| Pubchem: | 72683323 |
| Chemspiderid: | 59718542 |
| Synonyms: | Juncosamine |
| 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, 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] DMBMPP 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.
The (S,S)-isomer ((2S,6S)-DMBMPP) 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,[3] (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) | |
|---|---|---|---|---|
| [<sup>3</sup>H] ketanserin | [<sup>3</sup>H] 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 |