DMBMPP

DMBMPP
Clinical data
ATC code	None;
Legal status
Legal status	In general: uncontrolled;
Identifiers
	IUPAC name 2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine;
CAS Number	1391499-52-7 ;
PubChem CID	72683323;
Chemical and physical data
Formula	C21H26BrNO3
Molar mass	420.34 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC(C=C(Br)C(OC)=C1)=C1C[C@@H]2CCC[C@@H](C3=C(OC)C=CC=C3)N2;

DMBMPP, or 2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine, is an 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] 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 (S,S)-isomer (2S,6S-DMBMPP) is the most interesting scientifically as it is the most selective agonist for the human 5-HT_2A receptor yet discovered, with a K_i of 2.5 nM at the human 5-HT_2A receptor and with 124-fold selectivity for 5-HT_2A over the structurally similar 5-HT_2C-receptor.^[3] Together with 25CN-NBOH,^[4] 2S,6S-DMBMPP is the only known 5-HT_2A agonist to exhibit this level of selectivity.

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

References

^ Jose Juncosa (2011-05-07). "Organic synthesis combined with molecular modeling: A powerful approach to map the functional topography of dopamine and serotonin receptors". Purdue University.
^ Juncosa, J. I.; Hansen, M.; Bonner, L. A.; Cueva, J. P.; Maglathlin, R.; McCorvy, J. D.; Marona-Lewicka, D.; Lill, M. A.; Nichols, D. E. (2012). "Extensive rigid analogue design maps the binding conformation of potent N-benzylphenethylamine 5-HT2A serotonin receptor agonist ligands". ACS Chemical Neuroscience. 4: 120717095020003. doi:10.1021/cn3000668.
^ http://pubs.acs.org/doi/abs/10.1021/cn3000668
^ Hansen, M.; Phonekeo, K.; Paine, J. S.; Leth-Petersen, S.; Begtrup, M.; Bräuner-Osborne, H.; Kristensen, J. L. (2014). "Synthesis and Structure-Activity Relationships of N-Benzyl Phenethylamines as 5-HT_2A/2C Agonists". ACS Chemical Neuroscience. 5 (3): 243–9. doi:10.1021/cn400216u. PMC 3963123. PMID 24397362.

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[1] Jose Juncosa (2011-05-07). "Organic synthesis combined with molecular modeling: A powerful approach to map the functional topography of dopamine and serotonin receptors". Purdue University.

[2] Juncosa, J. I.; Hansen, M.; Bonner, L. A.; Cueva, J. P.; Maglathlin, R.; McCorvy, J. D.; Marona-Lewicka, D.; Lill, M. A.; Nichols, D. E. (2012). "Extensive rigid analogue design maps the binding conformation of potent N-benzylphenethylamine 5-HT2A serotonin receptor agonist ligands". ACS Chemical Neuroscience. 4: 120717095020003. doi:10.1021/cn3000668.

[3] ttp://pubs.acs.org/doi/abs/10.1021/cn3000668

[4] Hansen, M.; Phonekeo, K.; Paine, J. S.; Leth-Petersen, S.; Begtrup, M.; Bräuner-Osborne, H.; Kristensen, J. L. (2014). "Synthesis and Structure-Activity Relationships of N-Benzyl Phenethylamines as 5-HT_2A/2C Agonists". ACS Chemical Neuroscience. 5 (3): 243–9. doi:10.1021/cn400216u. PMC 3963123. PMID 24397362.

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Pharmacology

See also

References