Talk:DMBMPP

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DMBMPP
DMBMPP.svg
Chemical Nomenclature
Common names DMBMPP, Juncosamine
Systematic name 2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine
Class Membership
Psychoactive class Psychedelic
Chemical class Phenethylamine, Piperidine
Interactions


DMBMPP (also known as Juncosamine) is a novel psychedelic substance that is a modified analog of 25B-NBOMe. It was discovered in 2011 by Jose Juncosa in the group of David E. Nichols at Purdue University.

The (S,S)-isomer (2S,6S-DMBMPP) is the most interesting scientifically as it is the most selective agonist for the human 5-HT2A receptor yet discovered.


Chemistry

DMBMPP, or 2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine, is a 2-benzylpiperidine analog of the hallucinogenic N-benzylphenethylamine 25B-NBOMe.

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-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.[3] Together with 25CN-NBOH,[4] 2S,6S-DMBMPP is the only known 5-HT2A agonist to exhibit this level of selectivity.