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T-NBOMe

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T-NBOMe
Clinical data
Other namesTNBOMe; NBOMe-T; NBOMe-tryptamine; Tryptamine-NBOMe; N-(2-Methoxybenzyl)tryptamine
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Possible psychedelic drug
ATC code
  • None
Identifiers
  • 2-(1H-indol-3-yl)-N-[(2-methoxyphenyl)methyl]ethanamine
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H20N2O
Molar mass280.371 g·mol−1
3D model (JSmol)
  • COC1=CC=CC=C1CNCCC2=CNC3=CC=CC=C32
  • InChI=1S/C18H20N2O/c1-21-18-9-5-2-6-15(18)12-19-11-10-14-13-20-17-8-4-3-7-16(14)17/h2-9,13,19-20H,10-12H2,1H3
  • Key:HJCSKFSDXDPIKM-UHFFFAOYSA-N

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 (EC50Tooltip half-maximal effective concentration = 1,549 nM; EmaxTooltip maximal efficacy = 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

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References

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  1. ^ a b c d Yurchenko R, Yurchenko L, Galetskaya I, Pavlovets Y, Matsvei N (January 2024). "Recent trends in the identification of psychoactive substances". Recent Trends in the Field of Psychoactive Substance Identification (in Russian) (49). doi:10.13140/RG.2.2.33725.64484.
  2. ^ a b c d Heim R (2003). Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts (Thesis) (in German). 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. ^ a b 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. ^ a b c 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. doi:10.1007/s10822-010-9400-2. PMID 21088982.
  5. ^ a b c d e f g h Toro-Sazo M, Brea J, Loza MI, Cimadevila M, Cassels BK (2019). "5-HT2 receptor binding, functional activity and selectivity in N-benzyltryptamines". PLOS ONE. 14 (1) e0209804. Bibcode:2019PLoSO..1409804T. doi:10.1371/journal.pone.0209804. PMC 6328172. PMID 30629611.
  6. ^ Heim R, Pertz HH, Elz S (1999). "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.
  7. ^ Elz S, Heim R, Heil WL, Pertz HH (October 1999). "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. 332 (Suppl. 2). Jahrestagung, Frankfurt: Deutsche Pharmazeutische Gesellschaft (DPhG): 31.
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