Chemistry:5-MeO-T-NB3OMe

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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]

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] It is also not an explicitly controlled substance in the United States,[8] but it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

See also

References

  1. ↑ 1.0 1.1 "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chemical Reviews 124 (1): 124–163. January 2024. 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. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 "Effect of Hallucinogens on Unconditioned Behavior". Behavioral Neurobiology of Psychedelic Drugs. Curr Top Behav Neurosci. 36. 2018. pp. 159–199. doi:10.1007/7854_2016_466. ISBN 978-3-662-55878-2. 
  3. ↑ 3.0 3.1 "Analytical characterization of bioactive N-benzyl-substituted phenethylamines and 5-methoxytryptamines". Rapid Communications in Mass Spectrometry 29 (7): 573–584. April 2015. doi:10.1002/rcm.7134. PMID 26212274. Bibcode: 2015RCMS...29..573B. https://researchonline.ljmu.ac.uk/id/eprint/3409/5/RCM-14-0447.R1_SuppInfo%5B1%5D.pdf. 
  4. ↑ 4.0 4.1 4.2 4.3 4.4 4.5 4.6 4.7 4.8 "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. July 2015. doi:10.1021/cn500292d. PMID 25547199. 
  5. ↑ "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. ↑ Bryson N, "Novel benzyltryptamine compounds", WO patent 2023070228A1, published May 2023
  7. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  8. ↑ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026, https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf 



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