5-MeO-NBpBrT (5-Methoxy-N-(4-bromobenzyl)tryptamine) is a N-substituted member of the methoxytryptamine family of compounds. Like other such compounds it acts as an antagonist for the 5-HT2Areceptor, with a claimed 100x selectivity over the closely related 5-HT2C receptor.[1] While N-benzyl substitution of psychedelic phenethylamines often results in potent 5-HT2A agonists, it had been thought that N-benzyl tryptamines show much lower efficacy and are either very weak partial agonists or antagonists at 5-HT2A,[2][3] though more recent research has shown stronger agonist activity for 3-substituted benzyl derivatives.[4] Extending the benzyl group to a substituted phenethyl can also recover agonist activity in certain cases.[5]
^Glennon RA, Dukat M, el-Bermawy M, Law H, De los Angeles J, Teitler M, et al. (June 1994). "Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines". Journal of Medicinal Chemistry. 37 (13): 1929–35. doi:10.1021/jm00039a004. PMID 8027974.
^Silva M (2009). Theoretical study of the interaction of agonists with the 5-HT2A receptor (PhD thesis). Universität Regensburg.
^Silva ME, Heim R, Strasser A, Elz S, Dove S (January 2011). "Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor". Journal of Computer-Aided Molecular Design. 25 (1): 51–66. Bibcode:2011JCAMD..25...51S. CiteSeerX10.1.1.688.2670. doi:10.1007/s10822-010-9400-2. PMID 21088982. S2CID 3103050.
^Nichols DE, Sassano MF, Halberstadt AL, Klein LM, Brandt SD, Elliott SP, Fiedler WJ (July 2015). "N-Benzyl-5-methoxytryptamines as Potent Serotonin 5-HT2 Receptor Family Agonists and Comparison with a Series of Phenethylamine Analogues". ACS Chemical Neuroscience. 6 (7): 1165–75. doi:10.1021/cn500292d. PMC4505863. PMID 25547199.
^Jensen N (2004). Tryptamines as Ligands and Modulators of the Serotonin 5-HT2A Receptor and the Isolation of Aeruginascin from the Hallucinogenic Mushroom Inocybe aeruginascens(PDF) (PhD thesis). Georg-August-Universität zu Göttingen.
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nbpbrt, methoxy, bromobenzyl, tryptamine, substituted, member, methoxytryptamine, family, compounds, like, other, such, compounds, acts, antagonist, ht2a, receptor, with, claimed, 100x, selectivity, over, closely, related, ht2c, receptor, while, benzyl, substi. 5 MeO NBpBrT 5 Methoxy N 4 bromobenzyl tryptamine is a N substituted member of the methoxytryptamine family of compounds Like other such compounds it acts as an antagonist for the 5 HT2A receptor with a claimed 100x selectivity over the closely related 5 HT2C receptor 1 While N benzyl substitution of psychedelic phenethylamines often results in potent 5 HT2A agonists it had been thought that N benzyl tryptamines show much lower efficacy and are either very weak partial agonists or antagonists at 5 HT2A 2 3 though more recent research has shown stronger agonist activity for 3 substituted benzyl derivatives 4 Extending the benzyl group to a substituted phenethyl can also recover agonist activity in certain cases 5 5 MeO NBpBrTIdentifiersIUPAC name N 4 Bromobenzyl 2 5 methoxy 1H indol 3 yl ethanamineCAS Number155639 13 7 NPubChem CID5124753ChemSpider4299315 YUNIIUG43REN7BRChEMBLChEMBL57427 YChemical and physical dataFormulaC 18H 19Br N 2OMolar mass359 267 g mol 13D model JSmol Interactive imageSMILES BrC1 CC C CNCCC2 CNC3 CC C OC C C23 C C1InChI InChI 1S C18H19BrN2O c1 22 16 6 7 18 17 10 16 14 12 21 18 8 9 20 11 13 2 4 15 19 5 3 13 h2 7 10 12 20 21H 8 9 11H2 1H3 YKey XHLOUFPZLUULGI UHFFFAOYSA N Y N Y what is this verify See also Edit25B NBOMe 25I NBF RH 34References Edit Glennon RA Dukat M el Bermawy M Law H De los Angeles J Teitler M et al June 1994 Influence of amine substituents on 5 HT2A versus 5 HT2C binding of phenylalkyl and indolylalkylamines Journal of Medicinal Chemistry 37 13 1929 35 doi 10 1021 jm00039a004 PMID 8027974 Silva M 2009 Theoretical study of the interaction of agonists with the 5 HT2A receptor PhD thesis Universitat Regensburg Silva ME Heim R Strasser A Elz S Dove S January 2011 Theoretical studies on the interaction of partial agonists with the 5 HT2A receptor Journal of Computer Aided Molecular Design 25 1 51 66 Bibcode 2011JCAMD 25 51S CiteSeerX 10 1 1 688 2670 doi 10 1007 s10822 010 9400 2 PMID 21088982 S2CID 3103050 Nichols DE Sassano MF Halberstadt AL Klein LM Brandt SD Elliott SP Fiedler WJ July 2015 N Benzyl 5 methoxytryptamines as Potent Serotonin 5 HT2 Receptor Family Agonists and Comparison with a Series of Phenethylamine Analogues ACS Chemical Neuroscience 6 7 1165 75 doi 10 1021 cn500292d PMC 4505863 PMID 25547199 Jensen N 2004 Tryptamines as Ligands and Modulators of the Serotonin 5 HT2A Receptor and the Isolation of Aeruginascin from the Hallucinogenic Mushroom Inocybe aeruginascens PDF PhD thesis Georg August Universitat zu Gottingen This drug article relating to the nervous system is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title 5 MeO NBpBrT amp oldid 1075461200, wikipedia, wiki, book, books, library,
