5-MeO-T-NB3OMe

Last updated

5-MeO-T-NB3OMe
5MT-NB3OMe structure.png
Clinical data
Other names5MT-NB3OMe; NB3MeO-5-MeO-T; 5-MeO-T-NB3MeO; 5-MeO-NB3OMeT; N-(3-Methoxybenzyl)-5-methoxytryptamine
Drug class Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • 2-(5-methoxy-1H-indol-3-yl)-N-[(3-methoxyphenyl)methyl]ethanamine
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
Formula C19H22N2O2
Molar mass 310.397 g·mol−1
3D model (JSmol)
  • COC1=CC2=C(C=C1)NC=C2CCNCC3=CC(=CC=C3)OC
  • InChI=1S/C19H22N2O2/c1-22-16-5-3-4-14(10-16)12-20-9-8-15-13-21-19-7-6-17(23-2)11-18(15)19/h3-7,10-11,13,20-21H,8-9,12H2,1-2H3
  • Key:CJLDIVRTIQMENX-UHFFFAOYSA-N

5-MeO-T-NB3OMe, or 5MT-NB3OMe, also known as N-(3-methoxybenzyl)-5-methoxytryptamine, is a serotonin receptor modulator and psychedelic drug of the tryptamine, 5-methoxytryptamine, and N-benzyltryptamine families related to the 25-NB (NBOMe) psychedelics. [1] [2] [3] [4] It is a positional isomer of 5-MeO-T-NBOMe (5-MeO-T-NB2OMe). [2]

Contents

The drug shows affinity for many serotonin receptors and acts as an agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. [4] It had similar affinity and activational potency at the human serotonin 5-HT2A receptor as 5-MeO-T-NBOMe. [4] In addition, the drug had around 10-fold lower affinity for the human serotonin 5-HT2A receptor as 25I-NBOMe (25I-NB2OMe) but showed similar activational potency at this receptor as 25I-NBOMe. [4] 5-MeO-T-NB3OMe produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. [2] [4] It had similar potency in this test as 5-MeO-T-NBOMe and 25I-NB3OMe, but showed dramatically or 42- to 45-fold lower potency than 25I-NBOMe. [2] [4]

The chemical synthesis of 5-MeO-T-NB3OMe has been described. [4] Various analogues of 5-MeO-T-NB3OMe besides 5-MeO-T-NBOMe have also been described. [2] [4] [5] [6]

5-MeO-T-NB3OMe was first described in the scientific literature by David E. Nichols and colleagues in 2015. [1] [2] [3] [4] It is not a controlled substance in Canada as of 2025. [7]

See also

References

  1. 1 2 Duan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chemical Reviews. 124 (1): 124–163. doi:10.1021/acs.chemrev.3c00375. PMID   38033123. Interestingly, a study around a series of N-benzylated-5- methoxytryptamine analogues (Figure 7C) revealed that benzyl substitution led to compounds with very high affinity at the 5-HT2 family receptors.151 Various substituents on the phenyl group were well tolerated, but ortho and meta substitutions generally provided more potent compounds compared to the para substituted analogues (57−66, Figure 7C). Among them, compounds 65 (2-OMe) and 59 (3-OMe) displayed strong affinity at the h5-HT2AR (Ki = 1.51 and 1.05 nM, respectively; [ 125I]-DOI) as very potent partial agonists in the calcium flux assay (EC50 = 1.9 nM (Emax = 81%) and 6.2 nM (Emax = 52%), respectively). More importantly, compounds 65 and 59 were also tested in the HTR experiment, and they exhibited potent hallucinogenic effects with ED50 values of 3.15 nM and 3.28 nM, respectively.151 However, compounds 65 and 59 could also bind very potently to the 5- HT2CR (Ki = 3.39 nM and 5.89 nM, respectively) and the 5- HT2BR (Ki = 9 nM and 2.5 nM, respectively),151 therefore lacking subtype-selectivity for the 5-HT2AR.
  2. 1 2 3 4 5 6 Halberstadt AL, Geyer MA (2018). "Effect of Hallucinogens on Unconditioned Behavior". Behavioral Neurobiology of Psychedelic Drugs. Curr Top Behav Neurosci. Vol. 36. pp. 159–199. doi:10.1007/7854_2016_466. ISBN   978-3-662-55878-2. PMC   5787039 . PMID   28224459.
  3. 1 2 Brandt SD, Elliott SP, Kavanagh PV, Dempster NM, Meyer MR, Maurer HH, et al. (April 2015). "Analytical characterization of bioactive N-benzyl-substituted phenethylamines and 5-methoxytryptamines" (PDF). Rapid Communications in Mass Spectrometry. 29 (7): 573–584. Bibcode:2015RCMS...29..573B. doi:10.1002/rcm.7134. PMID   26212274.
  4. 1 2 3 4 5 6 7 8 9 Nichols DE, Sassano MF, Halberstadt AL, Klein LM, Brandt SD, Elliott SP, et al. (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): 1165–1175. doi:10.1021/cn500292d. PMC   4505863 . PMID   25547199.
  5. ↑ 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. ↑ WO 2023070228A1,Bryson N,"Novel benzyltryptamine compounds",published May 2023, assigned to Reunion Neuroscience Canada Inc.
  7. ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
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