Chemistry:25N-NBOMe

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25N-NBOMe, also known as 2C-N-NBOMe or NBOMe-2C-N, is a derivative of the hallucinogen 2C-N. The pharmacological properties of 25N-NBOMe have not been described in the scientific literature, but it is believed to act in a similar manner to related compounds such as 25I-NBOMe and 25C-NBOMe, which are potent agonists at the 5HT2A receptor.[1][2] 25N-NBOMe has been sold as a street drug and has only been described in the literature in terms of identification by forensic analysis.[3][4]

Use and effects

The dose range of 25N-NBOMe has been given as 0.1 to 1.3 mg or more sublingually, with a typical dose estimate of 0.6 mg.[5] Whereas 2C-N is much less potent in terms of dose than other 2C drugs, 25N-NBOMe appears to have a similar dose range as other NBOMe drugs.[5]

Toxicity and harm potential

This section is an excerpt from 25-NB § Toxicity and harm potential[ edit ]

Neurotoxic and cardiotoxic actions

This section is an excerpt from 25-NB § Neurotoxic and cardiotoxic actions[ edit ]

Emergency treatment

This section is an excerpt from 25-NB § Emergency treatment[ edit ]

Interactions

Pharmacology

Pharmacodynamics

25N-NBOMe activities
Target Affinity (Ki, nM)
5-HT1A 1,860–4,200 (Ki)
4,800 (EC50)
36% (Emax)
5-HT1B >10,000
5-HT1D 5,620
5-HT1E >10,000
5-HT1F ND
5-HT2A 0.11–1.41 (Ki)
0.204–70 (EC50)
34–173% (Emax)
5-HT2B 4.47–8.7 (Ki)
2.34–70 (EC50)
<10–58% (Emax)
5-HT2C 1.06–21 (Ki)
0.457–1.32 (EC50)
99–102% (Emax)
5-HT3 >10,000
5-HT4 ND
5-HT5A >10,000
5-HT6 55
5-HT7 >10,000
α1A 850–>10,000
α1B, α1D >10,000
α2A 501–590
α2B 1,100
α2C 692
β1 >10,000
β1 7,080
β3 >10,000
D1 18,000
D2 2,400–6,760
D3 2,190–4,500
D4 >10,000
D5 >10,000
H1 91–210
H2 1,070
H3, H4 >10,000
M1–M5 >10,000
I1 ND
σ1 537
σ2 58
MOR >10,000
DOR >10,000
KOR 2,820
TAAR1 >20,000 (Ki) (mouse)
2,200 (Ki) (rat)
>30,000 (EC50) (mouse)
1,500 (EC50) (rat)
>10,000 (EC50) (human)
IA (Emax) (mouse)
34% (Emax) (rat)
SERT 1,410–5,810 (Ki)
5,790–20,000 (IC50)
IA (EC50)
NET 7,200–11,300 (Ki)
15,000–33,000 (IC50)
IA (EC50)
DAT 13,000–37,900 (Ki)
245,000 (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: [6][7][8][9][10][11][12][13]

25N-NBOMe is a selective and highly potent agonist of the serotonin 5-HT2 receptors.[14] Its affinities (Ki) are 0.144 nM at the serotonin 5-HT2A receptor, 8.7 nM at the serotonin 5-HT2B receptor, and 1.06 nM at the serotonin 5-HT2C receptor.[14] In terms of affinity, the drug has approximately 7.4-fold selectivity for the serotonin 5-HT2A receptor over the serotonin 5-HT2C receptor and 60-fold selectivity for the 5-HT2A receptor over the serotonin 5-HT2B receptor.[14]

The EC50 (Emax) values of 25N-NBOMe are 0.51 nM (87.9%) at the serotonin 5-HT2A receptor, 47 nM (57.6%) at the serotonin 5-HT2B receptor, and 1.32 nM (99.4%) at the serotonin 5-HT2C receptor.[14] Hence, 25N-NBOMe is a full agonist of the serotonin 5-HT2A and 5-HT2C receptors and a partial agonist of the serotonin 5-HT2B receptor.[14] In terms of functional activity, 25N-NBOMe had 2.6-fold selectivity for the serotonin 5-HT2A receptor over the serotonin 5-HT2C receptor and 92-fold selectivity for the serotonin 5-HT2A receptor over the serotonin 5-HT2C receptor.[14]

In a 2023 study, the pharmacological properties of 25N-NBOMe (also referred to as compound 4) were extensively characterized using both in vitro and in vivo models.[15] Radioligand binding assays showed high binding affinity for serotonin 5-HT2 receptors, with pKi values of 9.26 ± 0.15 at 5-HT2A, 8.35 ± 0.08 at 5-HT2B, and 8.16 ± 0.07 at 5-HT2C. The compound was also screened across more than 40 additional CNS targets and found to be highly selective for the 5-HT2 receptor subfamily.[15]

In calcium flux functional assays, 25N-NBOMe was a potent full agonist at 5-HT2A (pEC50 = 9.50 ± 0.03; Emax = 94 ± 1%) and 5-HT2C (pEC50 = 9.07 ± 0.03; Emax = 102 ± 1%) receptors, while showing negligible agonist activity at 5-HT2B (Emax < 10%).[15]

Bioluminescence resonance energy transfer (BRET) functional assays measuring Gq dissociation and β-arrestin2 recruitment signaling indicated strong agonist activity at 5-HT2A, with Gq pEC50 = 9.69 ± 0.04 (Emax = 95.2 ± 1.2%) and β-arrestin2 recruitment pEC50 = 9.66 ± 0.09 (Emax = 136.5 ± 3.6%). This illustrates that 25N-NBOMe is a balanced 5-HT2A agonist across these pathways, in contrast to analogs like 25N-N1-Nap and 25N-NBPh which displayed functional selectivity or signaling bias for β-arrestin2 recruitment. For 5-HT2C, Gq pEC50 was 9.34 ± 0.08 (Emax = 100.0 ± 2.5%), while weak partial agonist activity was observed at 5-HT2B (pEC50 = 8.63 ± 0.14; Emax = 54.1 ± 2.5%).[15]

In vivo, 25N-NBOMe induced a robust head-twitch response (HTR) in mice with an ED50 of 0.11 mg/kg (0.29 μmol/kg). Notably 25N-NBOMe produced the highest HTR frequency (4.890 counts per minute) among a panel of structurally related 25N analogs.[15]

Unlike many other serotonergic psychedelics, 25N-NBOMe has shown reinforcing effects in rodents, including in terms of conditioned place preference (CPP) and self-administration.[16] 25N-NBOMe has been found to increase phosphorylation of the dopamine transporter (DAT) in the striatum similarly to methamphetamine in rodents.[17][16] DAT phosphorylation is associated with dopamine reverse transport and efflux, which in turn increases extracellular dopamine levels.[17][16]

History

25N-NBOMe was first described in the scientific literature by 2012.[18]

Society and culture

Canada

25N-NBOMe is a controlled substance in Canada under phenethylamine blanket-ban language.[19]

Hungary

25N-NBOMe is illegal in Hungary.[20]

Sweden

The Riksdag added 25N-NBOMe to Narcotic Drugs Punishments Act under swedish schedule I ("substances, plant materials and fungi which normally do not have medical use") as of January 16, 2015, published by Medical Products Agency (MPA) in regulation LVFS 2014:11 listed as 25N-NBOMe, and 2-(2,5-dimetoxi-4-nitrofenyl)-N-(2-metoxibensyl)etanamin.[21]

United Kingdom

This substance is a Class A drug in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause in the Misuse of Drugs Act 1971.[22]


United States

25N-NBOMe is not an explicitly controlled substance in the United States.[23] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

25N-NBOMe is illegal in Alabama.[24]

See also

Notes

References

  1. ↑ "Synthesis and Structure-Activity Relationships of N-Benzyl Phenethylamines as 5-HT2A/2C Agonists". ACS Chemical Neuroscience 5 (3): 243–249. Mar 2014. doi:10.1021/cn400216u. PMID 24397362. 
  2. ↑ 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.
  3. ↑ "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. 2012. https://www.justice.gov/dea/pr/microgram-journals/2012/mj9_84-109.pdf. Retrieved 14 January 2014. 
  4. ↑ "Two new synthetic cannabinoids, AM-2201 benzimidazole analog (FUBIMINA) and (4-methylpiperazin-1-yl)(1-pentyl-1H-indol-3-yl)methanone (MEPIRAPIM), and three phenethylamine derivatives, 25H-NBOMe 3,4,5-trimethoxybenzyl analog, 25B-NBOMe, and 2C-N-NBOMe, identified in illegal products". Forensic Toxicology 32 (1): 105–115. 2014. doi:10.1007/s11419-013-0217-2. 
  5. ↑ 5.0 5.1 "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. October 2018. doi:10.1093/ijnp/pyy047. PMID 29850881. "Supplementary Table S2. Dose estimates and data sources for psychedelics.". 
  6. ↑ "Kᵢ Database". 20 June 2025. https://pdspdb.unc.edu/kidb2/kidb/web/kis-results/index?KisResultsSearch%5Binput_receptors%5D=&KisResultsSearch%5Binput_sources%5D=&KisResultsSearch%5Binput_species%5D=&KisResultsSearch%5Binput_hot_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D%5B%5D=14700&KisResultsSearch%5Binput_test_ligands%5D%5B%5D=14682&KisResultsSearch%5Binput_citations%5D=&KisResultsSearch%5BsearchType%5D=&KisResultsSearch%5Bki_val_from%5D=&KisResultsSearch%5Bki_val_to%5D=&KisResultsSearch%5Bcustom_ki_val%5D=. 
  7. ↑ "Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)". Neuropharmacology 99: 546–553. December 2015. doi:10.1016/j.neuropharm.2015.08.034. PMID 26318099. https://psilosybiini.info/paperit/Receptor%20interaction%20profiles%20of%20novel%20N-2-methoxybenzyl%20(NBOMe)%20derivatives%20of%202,5-dimethoxy-substituted%20phenethylamines%20(2C%20drugs)%20(Rickli%20et%20al.,%202015).pdf. 
  8. ↑ "Neurochemical pharmacology of psychoactive substituted N-benzylphenethylamines: High potency agonists at 5-HT2A receptors". Biochem Pharmacol 158: 27–34. December 2018. doi:10.1016/j.bcp.2018.09.024. PMID 30261175. 
  9. ↑ "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. December 2020. doi:10.1016/j.forsciint.2020.110553. PMID 33160102. 
  10. ↑ "Structure-Activity Assessment and In-Depth Analysis of Biased Agonism in a Set of Phenylalkylamine 5-HT2A Receptor Agonists". ACS Chem Neurosci 14 (15): 2727–2742. August 2023. doi:10.1021/acschemneuro.3c00267. PMID 37474114. 
  11. ↑ "Selective, partial, and arrestin-biased 5-ht2a agonists with utility in various disorders". 11 May 2022. https://patents.google.com/patent/WO2022241006A1/. 
  12. ↑ "Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential". Nat Commun 14 (1). December 2023. doi:10.1038/s41467-023-44016-1. PMID 38102107. Bibcode: 2023NatCo..14.8221W. 
  13. ↑ "In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1". J Pharmacol Exp Ther 357 (1): 134–144. April 2016. doi:10.1124/jpet.115.229765. PMID 26791601. https://d1wqtxts1xzle7.cloudfront.net/74120533/eae6c6e62565b82d46b4d111bbea0f77b9c2-libre.pdf?1635931703=&response-content-disposition=inline%3B+filename%3DIn_Vitro_Characterization_of_Psychoactiv.pdf&Expires=1746838268&Signature=Sy4fJ90yUhxs68314NxYsW5PAaNrBGePRu35WRR4PIF-3YC7Z~sLdnCn5wfqqbLg9bDEGdt~oW55ugMP3D3jgA0BoRI~~GOb0NQOwrtfUEQK1PQs1uuN9qg5Y1ct8z5NsABm44RgtukkwRMdU6fO7OlfIsQ68hOiFk129Ll7UYqldxD2f1xhE2fTTfsxSpb8cMCJzHn7-ItqLdwnAUPFK7WggDIjmY1kCnaHLwIxMwdJCAq8L6DYzSTg7pZkbR8qlou~GXbTPQt~gYpyZTJp5hgW-7V6K5wLlQ7Z2xE7B0f9wEfuc1W1QNafg125Tr-vvAe4LEGKXV58bnn1bpfWKw__&Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA. 
  14. ↑ 14.0 14.1 14.2 14.3 14.4 14.5 "Neurochemical pharmacology of psychoactive substituted N-benzylphenethylamines: High potency agonists at 5-HT2A receptors". Biochemical Pharmacology 158: 27–34. December 2018. doi:10.1016/j.bcp.2018.09.024. PMID 30261175. 
  15. ↑ 15.0 15.1 15.2 15.3 15.4 "Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential". Nature Communications 14 (1): 8221. 2023. doi:10.1186/s12969-023-00927-3. PMID 38001451. 
  16. ↑ 16.0 16.1 16.2 "A novel designer drug, 25N-NBOMe, exhibits abuse potential via the dopaminergic system in rodents". Brain Research Bulletin 152: 19–26. October 2019. doi:10.1016/j.brainresbull.2019.07.002. PMID 31279579. 
  17. ↑ 17.0 17.1 "New designer phenethylamines 2C-C and 2C-P have abuse potential and induce neurotoxicity in rodents". Archives of Toxicology 95 (4): 1413–1429. April 2021. doi:10.1007/s00204-021-02980-x. PMID 33515270. Bibcode: 2021ArTox..95.1413K. "25N-NBOMe and other 2C drug derivatives similarly increased p-DAT levels in the NAc and striatum of mice (Seo et al. 2019). [...] increased p-DAT levels lead to an increase in dopamine release, which contribute to elevated dopamine levels.". 
  18. ↑ 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
  19. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  20. ↑ A Daath.hu kiegészítése a BSZKI "designer jogi listáján" nem szereplő, de az UP jegyzék 1.-4. szerkezeti leírásainak megfelelő, illetve az 5. felsorolásában szereplő néhány anyagról
  21. ↑ "Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika" (in sv). https://lakemedelsverket.se/upload/lvfs/LVFS_2014_11.pdf. 
  22. ↑ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014" (in en). http://www.legislation.gov.uk/uksi/2014/1106/made. 
  23. ↑ 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, https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf 
  24. ↑ Alabama Senate Bill SB 333: Controlled Substances



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