DMBMPP

DMBMPP, also known as juncosamine or as 2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine, is a highly selective serotonin 5-HT_2A receptor agonist and 2-benzylpiperidine analogue of the serotonergic psychedelic 25B-NBOMe which is used in scientific research.^[1][2][3][4]

DMBMPP

Clinical data
Other names	Juncosamine; 2-(2,5-Dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine
Drug class	Selective serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None
Identifiers
IUPAC name 2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine
CAS Number	1391499-52-7 Y
PubChem CID	72683323
ChemSpider	59718542
UNII	7H5TDL9Y6X
Chemical and physical data
Formula	C21H26BrNO3
Molar mass	420.347 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
InChI InChI=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 Key:KMVGLBONODPTDY-YJBOKZPZSA-N

Use

Research

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.^[5] 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.^[5] DMBMPP and 25CN-NBOH are the two most selective serotonin 5-HT_2A receptor agonists known as of 2020.^[6]

Pharmacology

The (S,S)-isomer ((2S,6S)-DMBMPP) is the most selective agonist for the human serotonin 5-HT_2A receptor yet discovered, with a affinity (K_i) of 2.5 nM at the human serotonin 5-HT_2A receptor and with 124-fold selectivity for the serotonin 5-HT_2A receptor over the structurally similar serotonin 5-HT_2C receptor.^[4][7] Together with 25CN-NBOH,^[8] (2S,6S)-DMBMPP is the only known 5-HT_2A agonist to exhibit this level of selectivity.^[5] In contrast to the case of the serotonin 5-HT_2A receptor, no functional data has been reported for DMBMPP at the serotonin 5-HT_2C receptor as of 2023.^[9][5]

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.^[10][11][4] As such, DMBMPP may be expected to have hallucinogenic effects in humans.^[10][11][4]

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.^[2] It differs from 25B-NBOMe by incorporating the amine within a piperidine ring, making for a more conformationally restrained or rigid molecular structure than that of the open-chain 25B-NBOMe.^[2] The presence of the piperidine ring introduces two stereocenters, thus, four stereoisomers of this compound can be made.^[2]

History

DMBMPP was first described in the scientific literature by Jose Juncosa of the lab of David E. Nichols at Purdue University in 2011.^[3][4]

See also

• Cyclized phenethylamine
• 25CN-NBOH
• DOB-NBOMe
• Z3517967757
• LPH-5