DMBMPP

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DMBMPP
File:DMBMPP.svg
Clinical data
Other namesJuncosamine; 2-(2,5-Dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine
Drug classSelective serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • 2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine
CAS Number
PubChem CID
ChemSpider
UNII
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC21H26BrNO3
Molar mass420.347 g·mol−1
3D model (JSmol)
  • COC(C=C(Br)C(OC)=C1)=C1C[C@@H]2CCC[C@@H](C3=C(OC)C=CC=C3)N2
  • 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

DMBMPP, also known as juncosamine or as 2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine, is a highly selective serotonin 5-HT2A receptor agonist and 2-benzylpiperidine analogue of the serotonergic psychedelic 25B-NBOMe which is used in scientific research.[1][2][3][4]

Interactions

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See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

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Pharmacodynamics

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The (S,S)-isomer ((2S,6S)-DMBMPP) is the most selective agonist for the human serotonin 5-HT2A receptor yet discovered, with a affinity (Ki) of 2.5 nM at the human serotonin 5-HT2A receptor and with 124-fold selectivity for the serotonin 5-HT2A receptor over the structurally similar serotonin 5-HT2C receptor.[4][5] Together with 25CN-NBOH,[6] (2S,6S)-DMBMPP is the only known 5-HT2A agonist to exhibit this level of selectivity.[7] In contrast to the case of the serotonin 5-HT2A receptor, no functional data has been reported for DMBMPP at the serotonin 5-HT2C receptor as of 2023.[8][7]

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.[9][10][4] As such, DMBMPP may be expected to have hallucinogenic effects in humans.[9][10][4]

Despite its uniquely high selectivity for the serotonin 5-HT2A 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.[7] Consequently, 25CN-NBOH, another highly selective serotonin 5-HT2A receptor agonist, has been proposed as an alternative to DMBMPP for use in scientific research.[7] DMBMPP and 25CN-NBOH are the two most selective serotonin 5-HT2A receptor agonists known as of 2020.[11]

Chemistry

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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, 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

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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

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References

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