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25T2-NBOMe

From Wikipedia, the free encyclopedia

Pharmaceutical compound
25T2-NBOMe
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 classSerotonin5-HT2 receptoragonist;Serotonergic psychedelic;Hallucinogen
ATC code
  • None
Identifiers
  • 2-(4-ethylsulfanyl-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
CAS Number
PubChemCID
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC20H27NO3S
Molar mass361.50 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 asN-(2-methoxybenzyl)-4-ethylthio-2,5-dimethoxyphenethylamine, is aserotonergic psychedelic of the25-NB (NBOMe) family.[2][3][4][5][6][7] It is the NBOMeanalogue of2C-T-2.[2][3][4][5][6][7]

Use and effects

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25T2-NBOMe's reported activedose range in humans has been described as 100 to 1,000 μg, with a typical dose estimate of 500 μg.[1] Theroute issublingual administration.[1]

Interactions

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

Pharmacology

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Pharmacodynamics

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25T2-NBOMe activities
TargetAffinity (Ki, nM)
5-HT1A2,200
5-HT1BND
5-HT1DND
5-HT1END
5-HT1FND
5-HT2A0.56–0.6 (Ki)
4.37–100 (EC50Tooltip half-maximal effective concentration)
38–81% (EmaxTooltip maximal efficacy)
5-HT2B0.85 (Ki)
40 (EC50)
31% (
Emax)
5-HT2C6.5 (Ki)
12.0 (EC50)
103% (
Emax)
5-HT3ND
5-HT4ND
5-HT5AND
5-HT684.9
5-HT7ND
α1A550
α1B,α1DND
α2A450
α2B,α2CND
β1β3ND
D17,700
D21,600
D33,000
D4,D5ND
H1490
H2H4ND
M1M5ND
I1ND
σ1,σ2ND
ORsND
TAAR1Tooltip 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)
SERTTooltip Serotonin transporter5,000 (Ki)
20,000 (IC50Tooltip half-maximal inhibitory concentration)
ND (EC50)
NETTooltip Norepinephrine transporter5,900 (Ki)
25,000 (IC50)
ND (EC50)
DATTooltip 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 highlypotent andselectiveagonist of theserotonin5-HT2 receptors.[11] Itsaffinities and activities at a variety of otherreceptors andtransporters have also been described.[11]

History

[edit]

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

See also

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References

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  1. ^abcLuethi 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. ^abHerian 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. ^abGil-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. ^abZawilska 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. ^abKyriakou 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. ^abHalberstadt 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. ^abMarchi 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. Retrieved15 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. ^abcRickli 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 fromthe 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.

External links

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