5-MeO-T-NBOMe

5-MeO-T-NBOMe
Clinical data
Other names5MT-NBOMe; NBOMe-5-MeO-T; 5-MeO-NBOMeT; N-(2-Methoxybenzyl)-5-methoxytryptamine
Drug classSerotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • 2-(5-methoxy-1H-indol-3-yl)-N-[(2-methoxyphenyl)methyl]ethanamine
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC19H22N2O2
Molar mass310.397 g·mol−1
3D model (JSmol)
  • COC1=CC2=C(C=C1)NC=C2CCNCC3=CC=CC=C3OC
  • InChI=1S/C19H22N2O2/c1-22-16-7-8-18-17(11-16)14(13-21-18)9-10-20-12-15-5-3-4-6-19(15)23-2/h3-8,11,13,20-21H,9-10,12H2,1-2H3
  • Key:OROYLKZKNDLGIQ-UHFFFAOYSA-N

5-MeO-T-NBOMe, also known as 5MT-NBOMe or NBOMe-5-MeO-T, is a psychedelic of the tryptamine family related to the 25-NB (NBOMe) drugs.[1][2][3] It has been sold online as a designer drug.[3][1][2]

Use and effects

5-MeO-T-NBOMe is said to produce hallucinogenic effects in humans.[3]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

5-MeO-T-NBOMe is a serotonin 5-HT2 receptor agonist and produces the head-twitch response in rodents.[1] However, compared to 25I-NBOMe, the drug is much less potent in producing the head-twitch response (~10-fold) and produces a much weaker maximal response (~25%).[1] 5-MeO-T-NBOMe is many times less potent than comparable phenethylamines such as 25C-NBOMe, but is still a reasonably potent and effective partial agonist for the 5-HT2 family of serotonin receptors.[1][2] A number of related compounds have also been developed, and in contrast to the phenethylamine counterparts the meta-substituted benzyl derivatives are in many cases more potent than the ortho-substituted benzyl compounds.[4]

Chemistry

Analogues of 5-MeO-T-NBOMe include N-benzyltryptamine (NBnT), 4-HO-NBnT, 5-MeO-NBnT, 5-MeO-T-NB3OMe, 5-MeO-NBpBrT, 5-MeO-N-DEAOP-NMT, and NEtPhOH-THPI, among others. It also shares structural similarities with pertines like oxypertine.

History

5-MeO-T-NBOMe was described by David E. Nichols and colleagues in 2015.[1] It was encountered online as a novel designer drug in 2023.[3]

Society and culture

Canada

5-MeO-T-NBOMe is not a controlled substance in Canada as of 2025.[5]

United States

5-MeO-T-NBOMe is not an explicitly controlled substance in the United States.[6] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

See also

References

  1. ^ a b c d e f 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.
  2. ^ a b c 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.
  3. ^ a b c d "5-MeO-T-NBOMe". АИПСИН (in Russian). Retrieved 1 January 2026.
  4. ^ WO 2023070228A1, Bryson N, "Novel benzyltryptamine compounds", published 2023 
  5. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
  6. ^ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026
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