25T2-NBOMe

Last updated

25T2-NBOMe
25T2-NBOMe structure.png
Clinical data
Other names2C-T-2-NBOMe; NBOMe-2C-T-2; N-(2-Methoxybenzyl)-4-ethylthio-2,5-dimethoxyphenethylamine
Routes of
administration 		Sublingual [1]
Drug class Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • 2-(4-ethylsulfanyl-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
CAS Number
PubChem CID
CompTox Dashboard (EPA)
Chemical and physical data
Formula C20H27NO3S
Molar mass 361.50 g·mol−1
3D model (JSmol)
  • CCSC1=C(C=C(C(=C1)OC)CCNCC2=CC=CC=C2OC)OC
  • InChI=1S/C20H27NO3S/c1-5-25-20-13-18(23-3)15(12-19(20)24-4)10-11-21-14-16-8-6-7-9-17(16)22-2/h6-9,12-13,21H,5,10-11,14H2,1-4H3
  • Key:OZEBFZPAWCXEGK-UHFFFAOYSA-N

25T2-NBOMe, also known as N-(2-methoxybenzyl)-4-ethylthio-2,5-dimethoxyphenethylamine, is a serotonergic psychedelic of the 25-NB (NBOMe) family. [2] [3] [4] [5] [6] [7] It is the NBOMe analogue of 2C-T-2. [2] [3] [4] [5] [6] [7]

Contents

Use and effects

25T2-NBOMe's reported active dose range in humans has been described as 100 to 1,000 μg, with a typical dose estimate of 500 μg. [1] The route is sublingual administration. [1]

Interactions

Pharmacology

Pharmacodynamics

25T2-NBOMe activities
Target Affinity (Ki, nM)
5-HT1A 2,200
5-HT1B ND
5-HT1D ND
5-HT1E ND
5-HT1F ND
5-HT2A 0.56–0.6 (Ki)
4.37–100 (EC50 Tooltip half-maximal effective concentration)
38–81% (Emax Tooltip maximal efficacy)
5-HT2B 0.85 (Ki)
40 (EC50)
31% (Emax)
5-HT2C 6.5 (Ki)
12.0 (EC50)
103% (Emax)
5-HT3 ND
5-HT4 ND
5-HT5A ND
5-HT6 84.9
5-HT7 ND
α1A 550
α1B, α1D ND
α2A 450
α2B, α2C ND
β1–β3 ND
D1 7,700
D2 1,600
D3 3,000
D4, D5 ND
H1 490
H2–H4 ND
M1–M5 ND
I1 ND
σ1, σ2 ND
ORs ND
TAAR1 Tooltip Trace amine-associated receptor 14,200 (Ki) (mouse)
350 (Ki) (rat)
2,900 (EC50) (mouse)
930 (EC50) (rat)
>10,000 (EC50) (human)
30% (Emax) (mouse)
24% (Emax) (rat)
SERT Tooltip Serotonin transporter5,000 (Ki)
20,000 (IC50 Tooltip half-maximal inhibitory concentration)
ND (EC50)
NET Tooltip Norepinephrine transporter5,900 (Ki)
25,000 (IC50)
ND (EC50)
DAT Tooltip Dopamine transporter8,600 (Ki)
67,000 (IC50)
ND (EC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [8] [9] [10] [11] [12]

25T2-NBOMe acts as a highly potent and selective agonist of the serotonin 5-HT2 receptors. [11] Its affinities and activities at a variety of other receptors and transporters have also been described. [11]

History

25T2-NBOMe was first described in the scientific literature by at least 2012. [13]

See also

References

  1. 1 2 3 Luethi D, Liechti ME (October 2018). "Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics". The International Journal of Neuropsychopharmacology. 21 (10): 926–931. doi:10.1093/ijnp/pyy047. PMC   6165951 . PMID   29850881.
  2. 1 2 Herian M, Świt P (January 2023). "25X-NBOMe compounds - chemistry, pharmacology and toxicology. A comprehensive review". Critical Reviews in Toxicology. 53 (1): 15–33. doi:10.1080/10408444.2023.2194907. PMID   37115704.
  3. 1 2 Gil-Martins E, Barbosa DJ, Borges F, Remião F, Silva R (June 2025). "Toxicodynamic insights of 2C and NBOMe drugs - Is there abuse potential?". Toxicology Reports. 14 101890. Bibcode:2025ToxR...1401890G. doi:10.1016/j.toxrep.2025.101890. PMC   11762925 . PMID   39867514.
  4. 1 2 Zawilska JB, Kacela M, Adamowicz P (2020). "NBOMes-Highly Potent and Toxic Alternatives of LSD". Frontiers in Neuroscience. 14: 78. doi: 10.3389/fnins.2020.00078 . PMC   7054380 . PMID   32174803.
  5. 1 2 Kyriakou C, Marinelli E, Frati P, Santurro A, Afxentiou M, Zaami S, et al. (September 2015). "NBOMe: new potent hallucinogens--pharmacology, analytical methods, toxicities, fatalities: a review" (PDF). European Review for Medical and Pharmacological Sciences. 19 (17): 3270–3281. PMID   26400534.
  6. 1 2 Halberstadt AL (2017). "Pharmacology and Toxicology of N-Benzylphenethylamine ("NBOMe") Hallucinogens". Neuropharmacology of New Psychoactive Substances (NPS). Curr Top Behav Neurosci. Vol. 32. pp. 283–311. doi:10.1007/7854_2016_64. ISBN   978-3-319-52442-9. PMID   28097528.{{cite book}}: |journal= ignored (help)
  7. 1 2 Marchi NC, Scherer JN, Fara LS, Remy L, Ornel R, Reis M, et al. (2019). "Clinical and Toxicological Profile of NBOMes: A Systematic Review". Psychosomatics. 60 (2): 129–138. doi:10.1016/j.psym.2018.11.002. PMID   30606495.
  8. ↑ "Kᵢ Database". PDSP. 15 July 2025. Retrieved 15 July 2025.
  9. ↑ Hansen M (2010-12-16). Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain (Ph.D. thesis). University of Copenhagen. doi:10.13140/RG.2.2.33671.14245.
  10. ↑ Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, et al. (19 March 2014). "Synthesis and Structure–Activity Relationships of N -Benzyl Phenethylamines as 5-HT 2A/2C Agonists". ACS Chemical Neuroscience. 5 (3): 243–249. doi: 10.1021/cn400216u . ISSN   1948-7193. PMC   3963123 . PMID   24397362.
  11. 1 2 3 Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME (December 2015). "Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)" (PDF). Neuropharmacology. 99: 546–553. doi:10.1016/j.neuropharm.2015.08.034. PMID   26318099.
  12. ↑ Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME (April 2016). "In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1" (PDF). The Journal of Pharmacology and Experimental Therapeutics. 357 (1): 134–144. doi:10.1124/jpet.115.229765. PMID   26791601. Archived from the original (PDF) on 2025-05-09.
  13. ↑ Casale JF, Hays PA (2012). "Characterization of eleven 2, 5-dimethoxy-N-(2-methoxybenzyl) phenethylamine (NBOMe) derivatives and differentiation from their 3-and 4-methoxybenzyl analogues—part I." (PDF). Microgram Journal. 9 (2): 84–109.


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