5-MeO-NBpBrT

5-MeO-NBpBrT
Identifiers
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
Formula C18H19BrN2O
Molar mass 359.260 g/mol
3D model (JSmol)
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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, 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

References

  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. ↑ 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.


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