Chemistry:5-MeO-NBnT

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5-MeO-NBnT, also known as N-benzyl-5-methoxytryptamine or as 5-MeO-T-NB, is a serotonin receptor agonist of the tryptamine and 5-methoxytryptamine families related to 5-MeO-NMT.[1][2][3][4]

Pharmacology

Pharmacodynamics

5-MeO-NBnT binds to the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors (Ki = 5.3–55 nM, 16.6 nM, and 95.5–370 nM, respectively).[2][4] It was assessed and found to be a potent partial agonist of the serotonin 5-HT2A receptor (EC50 = 20.4–100 nM; Emax = 30–63%) and full agonist of the serotonin 5-HT2C receptor (EC50 = 14.5 nM; Emax = 113%).[3][5][6][4] The drug was not evaluated in terms of effects in animals.[2][3][4]

Chemistry

Synthesis

The chemical synthesis of 5-MeO-NBnT has been described.[3]

Analogues

Analogues of 5-MeO-NBnT include N-benzyltryptamine (NBnT), 4-HO-NBnT, 5-MeO-NBOMeT, and 5-MeO-NB3OMeT, among others. It is also analogous to N-benzylphenethylamines, for instance 25-NB (NBOMe), 25B-NB (N-benzyl-2C-B), and 25I-NBOMe.

History

5-MeO-NBnT was first described in the scientific literature by Keijiro Takagi and colleagues by 1969.[1]

See also

References

  1. ↑ 1.0 1.1 "A potent competitive inhibitor of 5-hydroxytryptamine: 3-(2'-benzylaminoethyl)-5-methoxyindol hydrochloride". Japanese Journal of Pharmacology 19 (2): 234–239. June 1969. doi:10.1254/jjp.19.234. PMID 5308828. 
  2. ↑ 2.0 2.1 2.2 "Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines". Journal of Medicinal Chemistry 37 (13): 1929–1935. June 1994. doi:10.1021/jm00039a004. PMID 8027974. 
  3. ↑ 3.0 3.1 3.2 3.3 Heim R (2003). Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts (Thesis) (in Deutsch). Berlin: Freie Univ. Tab. 3-10. 5-HT2A-Rezeptoraktivität der N-Benzyl-2-(1H-indol-3-yl)ethylamin-Derivate 199 – 207, untersucht an 5-HT2ARezeptoren der isolierten Rattenschwanzarterie [...] [Compound:] 204 [...]
  4. ↑ 4.0 4.1 4.2 4.3 "5-HT2 receptor binding, functional activity and selectivity in N-benzyltryptamines". PLOS ONE 14 (1). 2019. doi:10.1371/journal.pone.0209804. PMID 30629611. Bibcode: 2019PLoSO..1409804T. 
  5. ↑ Silva M (2009). Theoretical study of the interaction of agonists with the 5-HT2A receptor (PhD.). Universität Regensburg. Table 5.1: Agonistic potency (pEC50) and intrinsic activity (Emax) of 5-HT2AR partial agonistic arylethylamines (indole, methoxybenzene and quinazolinedione derivatives) used in the study. [...] [Compound] 204 [...]
  6. ↑ "Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor". Journal of Computer-Aided Molecular Design 25 (1): 51–66. January 2011. doi:10.1007/s10822-010-9400-2. PMID 21088982. 



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