Chemistry:25D-NBOMe

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25D-NBOMe, also known as NBOMe-2C-D and "divination", is a derivative of the phenethylamine derived hallucinogen 2C-D. It acts in a similar manner to related compounds such as 25I-NBOMe, which is a potent agonist at the 5-HT2A receptor.[1][2] 25D-NBOMe has been sold as a street drug since 2010 and produces similar effects in humans to related compounds such as 25I-NBOMe and 25C-NBOMe.[3] It was banned as a Temporary Class Drug in the UK on 10 June 2013 after concerns about its recreational use.[4]

Use and effects

The dose range of 25D-NBOMe has been given as 0.3 to 1.2 mg or more sublingually, with a typical dose estimate of 1.0 mg.[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

25D-NBOMe activities
Target Affinity (Ki, nM)
5-HT1A 4,510–7,100 (Ki)
5,900 (EC50)
55% (Emax)
5-HT1B ND
5-HT1D 5,354
5-HT1E ND
5-HT1F ND
5-HT2A 0.22–2.52 (Ki)
0.224–90 (EC50)
27–148% (Emax)
5-HT2B 2.05–3.89 (Ki)
32.3–100 (EC50)
22–48% (Emax)
5-HT2C 0.69–13 (Ki)
1.37–11.5 (EC50)
96–97% (Emax)
5-HT3 ND
5-HT4 ND
5-HT5A ND
5-HT6 168.9
5-HT7 6,744
α1A 700
α1B, α1D ND
α2A 370
α2B, α2C ND
β1–β3 ND
D1 8,700
D2 2,600
D3 6,400
D4, D5 ND
H1 630
H2–H4 ND
M1–M5 ND
I1 ND
σ1, σ2 ND
MOR ND (Ki)
>63,000 (EC50)
<5–72% (Emax)
DOR ND
KOR ND
TAAR1 13,000 (Ki) (mouse)
810 (Ki) (rat)
4,000 (EC50) (mouse)
1,500 (EC50) (rat)
>30,000 (EC50) (human)
67% (Emax) (mouse)
34% (Emax) (rat)
SERT 1,400–1,780 (Ki)
1,024–3,900 (IC50)
IA (EC50)
NET 2,200–6,700 (Ki)
1,170–4,000 (IC50)
IA (EC50)
DAT 14,000–34,500 (Ki)
106,000 (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][14][15][16]

25D-NBOMe acts as an agonist of the serotonin 5-HT2 receptors.[17]

The drug produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.[18]

25D-NBOMe has shown reinforcing effects in rodents.[17][19] This included conditioned place preference (CPP) and self-administration.[17][19] Relatedly, the drug has been found to increase dopaminergic signaling in the nucleus accumbens.[17][19]

History

25D-NBOMe was first described in the scientific literature by 2012.[20]

Society and culture

China

As of October 2015 25D-NBOMe is a controlled substance in China.[21]

Finland

Scheduled in the "government decree on prohibited psychoactive substances in consumer markets".[22]

Sweden

Sveriges riksdag added 25D-NBOMe to schedule I ("substances, plant materials and fungi which normally do not have medical use") as narcotics in Sweden as of Aug 1, 2013, published by Medical Products Agency in their regulation LVFS 2013:15 listed as 25D-NBOMe 2-(2,5-dimetoxi-4-metylfenyl)-N-(2-metoxibensyl)etanamin.[23]

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.[24]


United States

Unregulated at a federal and state level, though arguably may contravene the Federal Analog Act under certain circumstances given its structural and functional similarity to controlled substance 2C-D.

See also

Notes

References

  1. ↑ "Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists". ACS Chemical Neuroscience 5 (3): 243–9. March 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.dea.gov/pr/microgram-journals/2012/mj9_84-109.pdf. Retrieved 14 January 2014. 
  4. ↑ "Temporary class drug order report on 5-6APB and NBOMe compounds". UK Home Office. 4 Jun 2013. https://www.gov.uk/government/publications/temporary-class-drug-order-report-on-benzofury-and-nbome-compounds. 
  5. ↑ "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=14681&KisResultsSearch%5Binput_citations%5D=&KisResultsSearch%5BsearchType%5D=&KisResultsSearch%5Bki_val_from%5D=&KisResultsSearch%5Bki_val_to%5D=&KisResultsSearch%5Bcustom_ki_val%5D=. 
  7. ↑ Liu, Tiqing. "BindingDB BDBM674338 2-(2,5-dimethoxy-4-methylphenyl)-N-(2-methoxybenzyl)ethan-1-amine::US20240166618, Compound 25D-NBOMe". https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=674338. 
  8. ↑ 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
  9. ↑ "Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists". ACS Chem Neurosci 5 (3): 243–249. March 2014. doi:10.1021/cn400216u. PMID 24397362. 
  10. ↑ "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. 
  11. ↑ "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. 
  12. ↑ "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. October 2020. doi:10.1007/s00204-020-02836-w. PMID 32627074. Bibcode: 2020ArTox..94.3449P. 
  13. ↑ "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. 
  14. ↑ "Selective, partial, and arrestin-biased 5-ht2a agonists with utility in various disorders". 11 May 2022. https://patents.google.com/patent/WO2022241006A1/. "Table 3. 5-HT2A in vitro G protein and arrestin functional activity of known 5-HT2A agonist psychedelics and novel compounds. No activity refers to no detectable curve. [...]" 
  15. ↑ "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. 
  16. ↑ "Off-target activity of NBOMes and NBOMe analogs at the µ opioid receptor". Arch Toxicol 97 (5): 1367–1384. May 2023. doi:10.1007/s00204-023-03465-9. PMID 36853332. Bibcode: 2023ArTox..97.1367D. 
  17. ↑ 17.0 17.1 17.2 17.3 "Toxicodynamic insights of 2C and NBOMe drugs - Is there abuse potential?". Toxicol Rep 14. June 2025. doi:10.1016/j.toxrep.2025.101890. PMID 39867514. Bibcode: 2025ToxR...1401890G. 
  18. ↑ "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species". Neuropharmacology 167. May 2020. doi:10.1016/j.neuropharm.2019.107933. PMID 31917152. PMC 9191653. http://usdbiology.com/cliff/Courses/Advanced%20Seminars%20in%20Neuroendocrinology/Serotonergic%20Psychedelics%2020/Halberstadt%2020%20Neuropharm%20potency%20of%20hallucinogens%20%20head-twitch.pdf. 
  19. ↑ 19.0 19.1 19.2 "Designer Drug, 25D-NBOMe, Has Reinforcing and Rewarding Effects through Change of a Dopaminergic Neurochemical System". ACS Chem Neurosci 14 (15): 2658–2666. August 2023. doi:10.1021/acschemneuro.3c00196. PMID 37463338. 
  20. ↑ 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
  21. ↑ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. http://www.sfda.gov.cn/WS01/CL0056/130753.html. 
  22. ↑ "Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista | 1130/2014 | Lainsäädäntö | Finlex". https://www.finlex.fi/fi/lainsaadanto/2014/1130. 
  23. ↑ "Läkemedelsverkets författningssamling" (in Swedish). Läkemedelsverkets. https://lakemedelsverket.se/upload/lvfs/LVFS_2013-15.pdf. 
  24. ↑ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014" (in en). http://www.legislation.gov.uk/uksi/2014/1106/made. 

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