25E-NBOMe
Width250px
ClassSerotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
Legal brF2
Legal br comment[1]
Legal deNpSG
Legal ukClass A
Cas number1354632-14-6
Pubchem118796522
Chemspiderid52085495
Unii02HX6G35T3
Synonyms2C-E-NBOMe; NBOMe-2C-E; N-(2-Methoxybenzyl)-4-ethyl-2,5-dimethoxyphenethylamine
Iupac name2-(4-ethyl-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethanamine
C20
H27
N1
O3
SmilesCOC(C=CC=C1)=C1CNCCC2=C(OC)C=C(CC)C(OC)=C2
Stdinchi1S/C20H27NO3/c1-5-15-12-20(24-4)16(13-19(15)23-3)10-11-21-14-17-8-6-7-9-18(17)22-2/h6-9,12-13,21H,5,10-11,14H2,1-4H3
StdinchikeyPXDVGFGXPVCNAB-UHFFFAOYSA-N

25E-NBOMe, also known as 2C-E-NBOMe or NBOMe-2C-E, is a derivative of the phenethylamine 2C-E. It acts in a similar manner to related compounds such as 25I-NBOMe, which are potent agonists at the 5-HT2A receptor.[2][3] 25E-NBOMe has been sold as a drug and produces similar effects in humans to related compounds such as 25I-NBOMe and 25C-NBOMe.

Use and effects

The dose range of 25E-NBOMe has been given as 0.1 to 1.0 mg sublingually, with a typical dose estimate of 0.3 mg.[4]

Interactions

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

Pharmacology

Pharmacodynamics

25E-NBOMe activities
TargetAffinity (Ki, nM)
5-HT1A1,680–3,500 (Ki)
13,700 (EC50)
38% (Emax)
5-HT1B3,593
5-HT1DND
5-HT1END
5-HT1FND
5-HT2A0.127–0.6 (Ki)
0.40–160 (EC50)
28–157% (Emax)
5-HT2B1.11–2.14 (Ki)
23.5–60 (EC50)
26–49% (Emax)
5-HT2C0.311–7.2 (Ki)
0.95–9.77 (EC50)
92–101% (Emax)
5-HT3ND
5-HT4ND
5-HT5AND
5-HT6148.3
5-HT7ND
α1A530
α1B, α1DND
α2A260
α2B, α2CND
β1–β3ND
D14,900
D21,500
D33,200
D4, D5ND
H11,400
H2–H4ND
M1–M5ND
I1ND
σ1, σ2ND
MORND (Ki)
>12,400 (EC50)
20–103% (Emax)
DORND
KORND
TAAR11,100 (Ki) (mouse)
260 (Ki) (rat)
1,800 (EC50) (mouse)
650 (EC50) (rat)
>10,000 (EC50) (human)
46% (Emax) (mouse)
37% (Emax) (rat)
SERT1,590–1,700 (Ki)
1,440–8,300 (IC50)
IA (EC50)
NET3,000–5,400 (Ki)
2,310–11,000 (IC50)
IA (EC50)
DAT8,100–19,600 (Ki)
34,000–100,000 (IC50)
IA (EC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [5][6][7][8][9][10][11][12][13]

25E-NBOMe acts as an agonist of the serotonin 5-HT2 receptors.[14] In accordance with its psychedelic effects in humans, it produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[14][15]

25E-NBOMe has shown reinforcing effects in rodents.[14][15] This included conditioned place preference (CPP) and self-administration.[14][15] The reinforcing effects of 25E-NBOMe were mediated by increased dopaminergic signaling in the nucleus accumbens.[14][15] Blockade of the dopamine D1 receptor could attenuate the CPP induced by 25E-NBOMe.[14][15]

History

25E-NBOMe was first described in the scientific literature by 2012.[16]

Society and culture

Canada

25E-NBOMe is a controlled substance in Canada under phenethylamine blanket-ban language.[17]

Sweden

Sweden's public health agency classified 25E-NBOMe as a narcotic substance, on January 18, 2019.[18]

United States

25E-NBOMe is not an explicitly controlled substance in the United States.[19] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

See also

References

  1. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União. Archived 2023-08-27 at the Wayback Machine. Retrieved 2023-08-27.
  2. ^ Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, Kristensen JL (March 2014). "Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists". ACS Chemical Neuroscience. 5 (3): 243–249. doi:10.1021/cn400216u. PMC 3963123. PMID 24397362
  3. ^ Hansen M (2010-12-16). Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain. (Ph.D.). University of Copenhagen. doi:10.13140/RG.2.2.33671.14245
  4. ^ Luethi D, Liechti ME (October 2018). "Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics". Int J Neuropsychopharmacol. 21 (10): 926–931. doi:10.1093/ijnp/pyy047. PMC 6165951. PMID 29850881 Supplementary Table S2. Dose estimates and data sources for psychedelics.
  5. ^ "Kᵢ Database". PDSP. 20 June 2025. Retrieved 20 June 2025.
  6. ^ Hansen, M. (2010). Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain: PhD Thesis. Faculty of Pharmaceutical Sciences, University of Copenhagen. https://bitnest.netfirms.com/external/Theses/Hansen2011
  7. ^ Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, Kristensen JL (March 2014). "Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists". ACS Chem Neurosci. 5 (3): 243–249. doi:10.1021/cn400216u. PMC 3963123. PMID 24397362
  8. ^ 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)". Neuropharmacology. 99: 546–553. doi:10.1016/j.neuropharm.2015.08.034. PMID 26318099
  9. ^ Eshleman AJ, Wolfrum KM, Reed JF, Kim SO, Johnson RA, Janowsky A (December 2018). "Neurochemical pharmacology of psychoactive substituted N-benzylphenethylamines: High potency agonists at 5-HT2A receptors". Biochem Pharmacol. 158: 27–34. doi:10.1016/j.bcp.2018.09.024. PMC 6298744. PMID 30261175
  10. ^ Pottie E, Cannaert A, Stove CP (October 2020). "In vitro structure-activity relationship determination of 30 psychedelic new psychoactive substances by means of β-arrestin 2 recruitment to the serotonin 2A receptor". Arch Toxicol. 94 (10): 3449–3460. Bibcode:2020ArTox..94.3449P. doi:10.1007/s00204-020-02836-w. PMID 32627074
  11. ^ 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 Sci Int. 317. doi:10.1016/j.forsciint.2020.110553. PMID 33160102
  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". J Pharmacol Exp Ther. 357 (1): 134–144. doi:10.1124/jpet.115.229765. PMID 26791601. Archived from the original on 2025-05-09.
  13. ^ Deventer MH, Persson M, Laus A, Pottie E, Cannaert A, Tocco G, Gréen H, Stove CP (May 2023). "Off-target activity of NBOMes and NBOMe analogs at the µ opioid receptor". Arch Toxicol. 97 (5): 1367–1384. Bibcode:2023ArTox..97.1367D. doi:10.1007/s00204-023-03465-9. hdl:11584/434705. PMID 36853332
  14. ^ Gil-Martins E, Barbosa DJ, Borges F, Remião F, Silva R (June 2025). "Toxicodynamic insights of 2C and NBOMe drugs - Is there abuse potential?". Toxicol Rep. 14. Bibcode:2025ToxR...1401890G. doi:10.1016/j.toxrep.2025.101890. PMC 11762925. PMID 39867514
  15. ^ Kim YJ, Kook WA, Ma SX, Lee BR, Ko YH, Kim SK, Lee Y, Lee JG, Lee S, Kim KM, Lee SY, Jang CG (April 2024). "The novel psychoactive substance 25E-NBOMe induces reward-related behaviors via dopamine D1 receptor signaling in male rodents". Arch Pharm Res. 47 (4): 360–376. doi:10.1007/s12272-024-01491-4. PMID 38551761
  16. ^ Casale, J. F., & Hays, P. A. (2012). Characterization of eleven 2, 5-dimethoxy-N-(2-methoxybenzyl) phenethylamine (NBOMe) derivatives and differentiation from their 3-and 4-methoxybenzyl analogues—part I. Microgram Journal, 9(2), 84–109. https://www.dea.gov/sites/default/files/pr/microgram-journals/2012/mj9_84-109.pdf
  17. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
  18. ^ "Sexton nya ämnen klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 18 January 2019. Archived from the original on 3 June 2021. Retrieved 11 November 2019.
  19. ^ "Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026)", United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026