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From Wikipedia, the free encyclopedia
Pharmaceutical compound
| Clinical data | |
|---|---|
| Other names | 2C-T-4-NBOMe; NBOMe-2C-T-4; N-(2-Methoxybenzyl)-4-isopropylthio-2,5-dimethoxyphenethylamine |
| Routes of administration | Sublingual[1] |
| Drug class | Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen |
| ATC code |
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| Identifiers | |
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| CAS Number | |
| PubChem CID | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C21H29NO3S |
| Molar mass | 375.53 g·mol−1 |
| 3D model (JSmol) | |
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25T4-NBOMe, also known as N-(2-methoxybenzyl)-4-isopropylthio-2,5-dimethoxyphenethylamine, is a serotonergic psychedelic of the 25-NB (NBOMe) family.[2][4][5] It is the NBOMe analogue of 2C-T-4.[2][4][5]
Use and effects
[edit]25T4-NBOMe's reported active dose range has been described as 150 to 1,200 μg, with a typical dose estimate of 500 μg.[1] The route is sublingual administration.[1]
Interactions
[edit]Pharmacology
[edit]Pharmacodynamics
[edit]| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT1A | 2,500 |
| 5-HT1B | ND |
| 5-HT1D | ND |
| 5-HT1E | ND |
| 5-HT1F | ND |
| 5-HT2A | 1.6 (Ki) 1.3–130 (EC50Tooltip half-maximal effective concentration) 46% (EmaxTooltip maximal efficacy) |
| 5-HT2B | ND (Ki) 200 (EC50) 27% (Emax) |
| 5-HT2C | 16 (Ki) ND (EC50) ND (Emax) |
| 5-HT3 | ND |
| 5-HT4 | ND |
| 5-HT5A | ND |
| 5-HT6 | ND |
| 5-HT7 | ND |
| α1A | 580 |
| α1B, α1D | ND |
| α2A | 260 |
| α2B, α2C | ND |
| β1–β3 | ND |
| D1 | 4,900 |
| D2 | 1,700 |
| D3 | 1,900 |
| D4, D5 | ND |
| H1 | 5,400 |
| H2–H4 | ND |
| M1–M5 | ND |
| I1 | ND |
| σ1, σ2 | ND |
| ORs | ND |
| TAAR1Tooltip Trace amine-associated receptor 1 | 1,500–1,600 (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 transporter | 8,100 (Ki) 14,000 (IC50Tooltip half-maximal inhibitory concentration) ND (EC50) |
| NETTooltip Norepinephrine transporter | 4,300 (Ki) 28,000 (IC50) ND (EC50) |
| DATTooltip Dopamine transporter | 6,200 (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 highly potent and selective agonist of the serotonin 5-HT2 receptors.[7][8] Its affinities and activities at a variety of other receptors and transporters have also been described.[7]
History
[edit]25T4-NBOMe was first described in the scientific literature by at least 2012.[10]
Society and culture
[edit]Legal status
[edit][edit]
25T4-NBOMe is a controlled substance in Canada under phenethylamine blanket-ban language.[11]
See also
[edit]References
[edit]- 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 . .
- Gil-Martins E, Barbosa DJ, Borges F, Remião F, Silva R (June 2025). . . 101890. :2025ToxR...1401890G. doi:10.1016/j.toxrep.2025.101890. PMC 11762925. PMID 39867514.
- 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". European Review for Medical and Pharmacological Sciences. 19 (17): 3270–3281. PMID 26400534.
- 1 2 Awuchi 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.
- ↑ "Kᵢ Database". PDSP. 15 July 2025. Retrieved 15 July 2025.
- 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.
- 1 2 Åstrand 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.
- ↑ 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 from the original (PDF) on 2025-05-09.
- ↑ 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.
- ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
External links
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