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Names

5-MeO-T-NBBr
N-(2-Bromobenzyl)-5-methoxytryptamine

IUPAC names

N-[(2-Bromophenyl)methyl]-2-(5-methoxy-1H-indol-3-yl)ethan-1-amine
N-(2-Bromobenzyl)-2-(5-methoxy-1H-indol-3-yl)ethan-1-amine

ID 1139 · Formula C₁₈H₁₉BrN₂O · Molecular weight 359.26

Tags Tryptamine

InChI InChI=1S/C18H19BrN2O/c1-22-15-6-7-18-16(10-15)13(12-21-18)8-9-20-11-14-4-2-3-5-17(14)19/h2-7,10,12,20-21H,8-9,11H2,1H3

InChI Key PRKRDRAHKDLIJD-UHFFFAOYSA-N This stereoisomer Any stereoisomer

SMILES COc1ccc2c(c1)c(CCNCc1ccccc1Br)c[nH]2

ChemSpider 115301495

Nichols, DE; Sassano, MF; Halberstadt, AL; Klein, LM; Brandt, SD; Elliott, SP; Fiedler, WJ. N-Benzyl-5-methoxytryptamines as potent serotonin 5-HT₂ receptor family agonists and comparison with a series of phenethylamine analogues ACS Chem. Neurosci., 15 Jul 2015, 6 (7), 1165-1175. 406 kB. https://doi.org/10.1021/cn500292d #5d MS,NMR

Brandt, SD; Elliott, SP; Kavanagh, PV; Dempster, NM; Meyer, MR; Maurer, HH; Nichols, DE. Analytical characterization of bioactive N-benzyl-substituted phenethylamines and 5-methoxytryptamines Rapid Commun. Mass Spectrom., 2 Mar 2015, 29 (7), 573–584. 2.2 MB. https://doi.org/10.1002/rcm.7134 #2d GC,LC,MS,UV

Halberstadt, AL; Geyer, MA. Effect of hallucinogens on unconditioned behavior In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 159-199. 879 kB. https://doi.org/10.1007/7854_2016_466

Toro-Sazo, M; Brea, J; Loza, MI; Cimadevila, M; Cassels, BK. 5-HT₂ receptor binding, functional activity and selectivity in N-benzyltryptamines PLOS ONE, 10 Jan 2019, 14 (1), e0209804. 1.1 MB. https://doi.org/10.1371/journal.pone.0209804 #40 NMR

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 #66

5-MeO-T-NB4Br · N-(4-Bromobenzyl)-5-methoxytryptamine

5-MeO-T-NB3Br · N-(3-bromobenzyl)-5-methoxytryptamine

N-(2-Methoxy-5-bromobenzyl)tryptamine · T-NBOMe5Br

7 Dec 2019 · · Isomer Design