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Names

DMBMPP
Juncosamine

IUPAC name

(2S,6S)-2-[(4-Bromo-2,5-dimethoxyphenyl)methyl]-6-(2-methoxyphenyl)piperidine

ID 1238 · Formula C₂₁H₂₆BrNO₃ · Molecular weight 420.34

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

InChI Key KMVGLBONODPTDY-YJBOKZPZSA-N This stereoisomer Any stereoisomer

SMILES COc1cc(Br)c(cc1C[C@@H]1CCC[C@H](N1)c1ccccc1OC)OC

ChemSpider 59718542
PubChem 60208938
Wikidata Q15708268
Wikipedia DMBMPP
Wikipedia, see also 25-NB
Wikipedia, see also List of methylphenidate analogues

Phenethylamine: Von der Strucktur zur Funktion 8.5 (439) 866, 867

Juncosa, JI; Hansen, M; Bonner, LA; Cueva, JP; Maglathlin, R; McCorvy, JD; Marona-Lewicka, D; Lill, MA; Nichols, DE. Extensive rigid analogue design maps the binding conformation of potent N-benzylphenethylamine 5-HT_2A serotonin receptor agonist ligands ACS Chem. Neurosci., 16 Jan 2013, 4 (1), 96-109. 3.8 MB. https://doi.org/10.1021/cn3000668 #9 MS,NMR

Hansen, M. Design and synthesis of selective serotonin receptor agonists for positron emission tomography imaging of the brain Ph. D. Thesis, University of Copenhagen, 16 Dec 2012. 7.9 MB. #4.7 NMR

Halberstadt, AL. Pharmacology and Toxicology of N-Benzylphenethylamine (“NBOMe”) Hallucinogens In Neuropharmacology of New Psychoactive Substances (NPS): The Science Behind the Headlines; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 18 Jan 2017; pp 283-311. 826 kB. https://doi.org/10.1007/7854_2016_64

Nichols, DE. Chemistry and structure–activity relationships of psychedelics In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 1-43. 2.6 MB. https://doi.org/10.1007/7854_2017_475 #77

Poulie, CBM; Jensen, AA; Halberstadt, AL; Kristensen, JL. DARK Classics in Chemical Neuroscience: NBOMes ACS Chem. Neurosci., 2 Dec 2020, 11 (23), 3860-3869. 860 kB. https://doi.org/10.1021/acschemneuro.9b00528 #DMBMPP

Rørsted, EM; Jensen, AA; Kristensen, JL. 25CN‐NBOH: A selective agonist for in vitro and in vivo investigations of the serotonin 2A receptor ChemMedChem, 21 Aug 2021, 16 (21), 3263-3270. 1.7 MB. https://doi.org/10.1002/cmdc.202100395 #DMBMPP

Halberstadt, AL. Recent advances in the neuropsychopharmacology of serotonergic hallucinogens Behav. Brain Res., 15 Jan 2015, 277, 99–120. 4.1 MB. https://doi.org/10.1016/j.bbr.2014.07.016 #DMBMPP

Marcher-Rørsted, E; Nykodemová, J; Harpsøe, K; Jensen, AA; Kristensen, JL. Introducing conformational restraints on 25CN-NBOH: A selective 5-HT_2A receptor agonist ACS Med. Chem. Lett., 9 Mar 2023, 14 (3), 319–325. 8.9 MB. https://doi.org/10.1021/acsmedchemlett.3c00014 #2 LC,MS,NMR,TLC

Duan, W; Cao, D; Wang, S; Cheng, J. Serotonin 2A receptor (5-HT_2AR) agonists: Psychedelics and non-hallucinogenic analogues as emerging antidepressants Chem. Rev., 10 Jan 2024, 124 (1), 124–163. 12.6 MB. https://doi.org/10.1021/acs.chemrev.3c00375 #158

2C-B-3PIP-NBOMe

7 Dec 2019 · · Isomer Design