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5-MeO-NBpBrT

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5-MeO-NBpBrT
Identifiers
  • N-(4-Bromobenzyl)-2-(5-methoxy-1H-indol-3-yl)ethanamine
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H19BrN2O
Molar mass359.260 g/mol g·mol−1
3D model (JSmol)
  • c3cc(Br)ccc3CNCCc(cnc1cc2)c1cc2OC
  • 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 checkY
  • Key:XHLOUFPZLUULGI-UHFFFAOYSA-N checkY
  (verify)

5-MeO-NBpBrT (5-Methoxy-N-(4-bromobenzyl)tryptamine) is a drug which 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

References

  1. ^ Glennon RA, Dukat M, el-Bermawy M, Law H, De los Angeles J, Teitler M, King A, Herrick-Davis K. Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines. Journal of Medicinal Chemistry. 1994 Jun 24;37(13):1929-35. 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.
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