DMBMPP

DMBMPP

Systematic (IUPAC) name
2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine
Clinical data
Legal status	Uncontrolled
Identifiers
CAS Number	1391499-52-7 N
ATC code	None
PubChem	CID: 72683323
Chemical data
Formula	C21H26BrNO3
Molecular mass	420.34 g/mol
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. 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. Together with 25CN-NBOH, 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

See also

• 25CN-NBOH
• 25B-NBOMe