5-MeO-NBpBrT

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-NBpBrT
Identifiers
IUPAC name
  • N-(4-Bromobenzyl)-2-(5-methoxy-1H-indol-3-yl)ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC18H19BrN2O
Molar mass359.267 g·mol−1
3D model (JSmol)
SMILES
  • BrC1=CC=C(CNCCC2=CNC3=CC=C(OC)C=C23)C=C1
InChI
  • 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 Y
  • Key:XHLOUFPZLUULGI-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

See also

References
  1. 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.
  2. Silva M (2009). Theoretical study of the interaction of agonists with the 5-HT2A receptor (PhD thesis). Universität Regensburg.
  3. 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.
  4. 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.
  5. 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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