5-MeO-NBpBrT

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5-MeO-NBpBrT
5-MeO-NBpBrT structure.png
Systematic (IUPAC) name
N-(4-Bromobenzyl)-2-(5-methoxy-1H-indol-3-yl)ethanamine
Identifiers
CAS Number 155639-13-7 YesY
PubChem CID 5124753
ChemSpider 4299315 YesY
ChEMBL CHEMBL57427 YesY
Chemical data
Formula C18H19BrN2O
Molar mass 359.260 g/mol
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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, N-benzyl tryptamines show much lower efficacy and are either very weak partial agonists or antagonists at 5-HT2A.[2][3] Extending the benzyl group to a substituted phenethyl can however recover agonist activity in certain cases.[4]

See also[edit]

References[edit]

  1. ^ Glennon, RA; Dukat, M; el-Bermawy, M; Law, H; De los Angeles, J; Teitler, M; King, A; Herrick-Davis, K (24 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. 
  2. ^ Maria Silva PhD. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Universität Regensburg, 2009.
  3. ^ Silva ME; Heim R; Strasser A; Elz S; Dove S (January 2011). "Theoretical studies on the interaction of partial agonists with the 5-HT(2A) receptor". Journal of Computer-aided Molecular Design 25 (1): 51–66. doi:10.1007/s10822-010-9400-2. PMID 21088982. 
  4. ^ 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.