Chemistry:T-NBOMe

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T-NBOMe, or TNBOMe, also known as NBOMe-T, NBOMe-tryptamine, or N-(2-methoxybenzyl)tryptamine, is a serotonin receptor modulator and possible psychedelic drug of the tryptamine family.[1][2][3][4][5] It is the N-(2-methoxybenzyl) derivative of tryptamine.[1][2][4][5]

The drug shows affinity for the serotonin 5-HT2 receptors, including for the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors (Ki = 89 nM, 47 nM, and 224 nM, respectively).[5] It shows 46-fold higher affinity for the serotonin 5-HT2A receptor than tryptamine (Ki = 89 nM vs. 4,074 nM, respectively).[5] T-NBOMe acts as a partial agonist of the serotonin 5-HT2A receptor (EC50 = 1,549 nM; Emax = 63%) and as a near-full agonist of the serotonin 5-HT2C receptor (EC50 = 35 nM; Emax = 94%), with 44-fold preference for activation of the serotonin 5-HT2C receptor over the serotonin 5-HT2A receptor.[5] Whereas T-NBOMe had much higher affinity for the serotonin 5-HT2A receptor than tryptamine, it showed 89-fold lower activational potency at the serotonin 5-HT2A receptor than tryptamine and also had lower activational efficacy at the receptor.[5] In an earlier study however, T-NBOMe showed much greater potency as an agonist of the serotonin 5-HT2A receptor (EC50 = 155 nM; Emax = 44%).[2][3][4][5]

The chemical synthesis of T-NBOMe has been described.[2][5]

T-NBOMe was first described in the scientific literature by Ralf Heim and colleagues in 1999.[6][7] It emerged as a novel designer drug by early 2024.[1] However, the properties and effects of T-NBOMe in humans are unknown and it is unclear whether T-NBOMe actually produces hallucinogenic effects.[1]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 "Recent trends in the identification of psychoactive substances." (in Russian). Recent Trends in the Field of Psychoactive Substance Identification (49). January 2024. doi:10.13140/RG.2.2.33725.64484. 
  2. ↑ 2.0 2.1 2.2 2.3 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:] 201 [...]
  3. ↑ 3.0 3.1 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. [...]
  4. ↑ 4.0 4.1 4.2 "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. Bibcode: 2011JCAMD..25...51S. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=57923f10abb4717589fdbe8dc2be132b0e9ac7aa. 
  5. ↑ 5.0 5.1 5.2 5.3 5.4 5.5 5.6 5.7 "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. 
  6. ↑ "Preparation and in vitro pharmacology of novel secondary amine-type 5-HT2A receptor agonists: from submillimolar to subnanomolar activity.". Arch. Pharm. Pharm. Med. Chem 332: 34. 1999. https://bitnest.netfirms.com/external/Arch.Pharm.Pharm.Med.Chem/331.S1.34. 
  7. ↑ "Partial agonists for vascular 5-HT2A-receptors: Selectivity studies vis-à-vis to 5-HT1B, 5-HT3 and 5-HT4 receptors, Poster presentation (S10)". Arch. Pharm. Pharm. Med Chem. (Jahrestagung, Frankfurt: Deutsche Pharmazeutische Gesellschaft (DPhG)) 332 (Suppl. 2): 31. October 1999. https://isomerdesign.com/bitnest/external/Arch.Pharm.Pharm.Med.Chem/331.S2.10. 



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