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25T4-NBOMe

From Wikipedia, the free encyclopedia

Pharmaceutical compound
25T4-NBOMe
Clinical data
Other names2C-T-4-NBOMe; NBOMe-2C-T-4;N-(2-Methoxybenzyl)-4-isopropylthio-2,5-dimethoxyphenethylamine
Routes of
administration
Sublingual[1]
Drug classSerotonin5-HT2 receptoragonist;Serotonergic psychedelic;Hallucinogen
ATC code
  • None
Identifiers
  • 2-(2,5-dimethoxy-4-propan-2-ylsulfanylphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
CAS Number
PubChemCID
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC21H29NO3S
Molar mass375.53 g·mol−1
3D model (JSmol)
  • CC(C)SC1=C(C=C(C(=C1)OC)CCNCC2=CC=CC=C2OC)OC
  • InChI=1S/C21H29NO3S/c1-15(2)26-21-13-19(24-4)16(12-20(21)25-5)10-11-22-14-17-8-6-7-9-18(17)23-3/h6-9,12-13,15,22H,10-11,14H2,1-5H3
  • Key:BOWHVFJVXBVJCU-UHFFFAOYSA-N

25T4-NBOMe, also known asN-(2-methoxybenzyl)-4-isopropylthio-2,5-dimethoxyphenethylamine, is aserotonergic psychedelic of the25-NB (NBOMe) family.[2][3][4][5] It is the NBOMeanalogue of2C-T-4.[2][3][4][5]

Use and effects

[edit]

25T4-NBOMe's reported activedose range has been described as 150 to 1,200 μg, with a typical dose estimate of 500 μg.[1] Theroute issublingual administration.[1]

Interactions

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

Pharmacology

[edit]

Pharmacodynamics

[edit]
25T4-NBOMe activities
TargetAffinity (Ki, nM)
5-HT1A2,500
5-HT1BND
5-HT1DND
5-HT1END
5-HT1FND
5-HT2A1.6 (Ki)
1.3–130 (EC50Tooltip half-maximal effective concentration)
46% (EmaxTooltip maximal efficacy)
5-HT2BND (Ki)
200 (
EC50)
27% (
Emax)
5-HT2C16 (Ki)
ND (EC50)
ND (Emax)
5-HT3ND
5-HT4ND
5-HT5AND
5-HT6ND
5-HT7ND
α1A580
α1B,α1DND
α2A260
α2B,α2CND
β1β3ND
D14,900
D21,700
D31,900
D4,D5ND
H15,400
H2H4ND
M1M5ND
I1ND
σ1,σ2ND
ORsND
TAAR1Tooltip Trace amine-associated receptor 11,500–1,600 (Ki) (mouse)
120 (Ki) (rat)
4,700 (EC50) (mouse)
1,100 (
EC50) (rat)
>10,000 (
EC50) (human)
33% (
Emax) (mouse)
31% (
Emax) (rat)
SERTTooltip Serotonin transporter8,100 (Ki)
14,000 (IC50Tooltip half-maximal inhibitory concentration)
ND (EC50)
NETTooltip Norepinephrine transporter4,300 (Ki)
28,000 (IC50)
ND (EC50)
DATTooltip Dopamine transporter6,200 (Ki)
58,000 (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:[6][7][8][9]

25T4-NBOMe acts as a highlypotent andselectiveagonist of theserotonin5-HT2 receptors.[7][8] Itsaffinities and activities at a variety of otherreceptors andtransporters have also been described.[7]

History

[edit]

25T4-NBOMe was first described in thescientific literature by at least 2012.[10]

See also

[edit]

References

[edit]
  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. ^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.
  3. ^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.
  4. ^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".European Review for Medical and Pharmacological Sciences.19 (17):3270–3281.PMID 26400534.
  5. ^abAwuchi CG, Aja MP, Mitaki NB, Morya S, Amagwula IO, Echeta CK, et al. (2 February 2023)."New Psychoactive Substances: Major Groups, Laboratory Testing Challenges, Public Health Concerns, and Community-Based Solutions".Journal of Chemistry.2023:1–36.doi:10.1155/2023/5852315.ISSN 2090-9071.S2CID 256567458.
  6. ^"Kᵢ Database".PDSP. 15 July 2025. Retrieved15 July 2025.
  7. ^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.
  8. ^abÅstrand A, Guerrieri D, Vikingsson S, Kronstrand R, Green H (December 2020). "In vitro characterization of new psychoactive substances at the μ-opioid, CB1, 5HT1A, and 5-HT2A receptors-On-target receptor potency and efficacy, and off-target effects".Forensic Science International.317 110553.doi:10.1016/j.forsciint.2020.110553.PMID 33160102.
  9. ^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).J Pharmacol Exp Ther.357 (1):134–144.doi:10.1124/jpet.115.229765.PMID 26791601. Archived fromthe original(PDF) on 2025-05-09.
  10. ^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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