| 词条 | 5-MeO-NBpBrT |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477345825 | IUPAC_name = N-(4-Bromobenzyl)-2-(5-methoxy-1H-indol-3-yl)ethanamine | image = 5-MeO-NBpBrT_structure.png | tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = {{cascite|changed|??}} | CAS_number = 155639-13-7 | ATC_prefix = | ATC_suffix = | ATC_supplemental = | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 57427 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = XHLOUFPZLUULGI-UHFFFAOYSA-N | PubChem = 5124753 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 4299315 | chemical_formula = | C=18 | H=19 | Br=1 | N=2 | O=1 | molecular_weight = 359.260 g/mol | smiles = BrC1=CC=C(CNCCC2=CNC3=CC=C(OC)C=C23)C=C1 }}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] See also
References1. ^{{cite journal|last1=Glennon|first1=RA|last2=Dukat|first2=M|last3=el-Bermawy|first3=M|last4=Law|first4=H|last5=De los Angeles|first5=J|last6=Teitler|first6=M|last7=King|first7=A|last8=Herrick-Davis|first8=K|title=Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines.|journal=Journal of Medicinal Chemistry|date=24 June 1994|volume=37|issue=13|pages=1929–35|pmid=8027974|doi=10.1021/jm00039a004}} {{Serotonergics}}{{Tryptamines}}{{nervous-system-drug-stub}}2. ^Maria Silva PhD. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Universität Regensburg, 2009. 3. ^{{cite journal |author =Silva ME |author2 =Heim R |author3 =Strasser A|author4 = Elz S |author5 =Dove S |title=Theoretical studies on the interaction of partial agonists with the 5-HT(2A) receptor |journal=Journal of Computer-aided Molecular Design |volume=25 |issue=1 |pages=51–66 |date=January 2011 |pmid=21088982 |doi=10.1007/s10822-010-9400-2|citeseerx =10.1.1.688.2670 }} 4. ^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. 2015 Jul 15;6(7):1165-75. doi: 10.1021/cn500292d. {{PMID|25547199}} 5. ^Niels Jensen. Tryptamines as Ligands and Modulators of the Serotonin 5-HT2A Receptor and the Isolation of Aeruginascin from the Hallucinogenic Mushroom Inocybe aeruginascens. PhD dissertation, Georg-August-Universität zu Göttingen, 2004. 2 : 5-HT2A antagonists|Tryptamines |
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