Chemistry:25E-NBOMe

From HandWiki

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.[1][2] 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.[3]

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

25E-NBOMe activities
Target Affinity (Ki, nM)
5-HT1A 1,680–3,500 (Ki)
13,700 (EC50)
38% (Emax)
5-HT1B 3,593
5-HT1D ND
5-HT1E ND
5-HT1F ND
5-HT2A 0.127–0.6 (Ki)
0.40–160 (EC50)
28–157% (Emax)
5-HT2B 1.11–2.14 (Ki)
23.5–60 (EC50)
26–49% (Emax)
5-HT2C 0.311–7.2 (Ki)
0.95–9.77 (EC50)
92–101% (Emax)
5-HT3 ND
5-HT4 ND
5-HT5A ND
5-HT6 148.3
5-HT7 ND
α1A 530
α1B, α1D ND
α2A 260
α2B, α2C ND
β1–β3 ND
D1 4,900
D2 1,500
D3 3,200
D4, D5 ND
H1 1,400
H2–H4 ND
M1–M5 ND
I1 ND
σ1, σ2 ND
MOR ND (Ki)
>12,400 (EC50)
20–103% (Emax)
DOR ND
KOR ND
TAAR1 1,100 (Ki) (mouse)
260 (Ki) (rat)
1,800 (EC50) (mouse)
650 (EC50) (rat)
>10,000 (EC50) (human)
46% (Emax) (mouse)
37% (Emax) (rat)
SERT 1,590–1,700 (Ki)
1,440–8,300 (IC50)
IA (EC50)
NET 3,000–5,400 (Ki)
2,310–11,000 (IC50)
IA (EC50)
DAT 8,100–19,600 (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: [4][5][6][7][8][9][10][11][12]

25E-NBOMe acts as an agonist of the serotonin 5-HT2 receptors.[13] In accordance with its psychedelic effects in humans, it produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[13][14]

25E-NBOMe has shown reinforcing effects in rodents.[13][14] This included conditioned place preference (CPP) and self-administration.[13][14] The reinforcing effects of 25E-NBOMe were mediated by increased dopaminergic signaling in the nucleus accumbens.[13][14] Blockade of the dopamine D1 receptor could attenuate the CPP induced by 25E-NBOMe.[13][14]

History

25E-NBOMe was first described in the scientific literature by 2012.[15]

Society and culture

Canada

25E-NBOMe is a controlled substance in Canada under phenethylamine blanket-ban language.[16]

Sweden

Sweden's public health agency classified 25E-NBOMe as a narcotic substance, on January 18, 2019.[17]

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.[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

Notes

References

  1. ↑ "Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists". ACS Chemical Neuroscience 5 (3): 243–249. 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. ↑ "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.". 
  4. ↑ "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=. 
  5. ↑ 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
  6. ↑ "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. 
  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 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. 
  10. ↑ "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. 
  11. ↑ "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. 
  12. ↑ "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. 
  13. ↑ 13.0 13.1 13.2 13.3 13.4 13.5 "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. 
  14. ↑ 14.0 14.1 14.2 14.3 14.4 "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. April 2024. doi:10.1007/s12272-024-01491-4. PMID 38551761. 
  15. ↑ 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
  16. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  17. ↑ "Sexton nya ämnen klassas som narkotika eller hälsofarlig vara" (in sv). Folkhälsomyndigheten. 18 January 2019. https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2019/januari/sexton-nya-amnen-klassas-som-narkotika-eller-halsofarlig-vara/. 
  18. ↑ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014" (in en). http://www.legislation.gov.uk/uksi/2014/1106/made. 
  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, https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf 



Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:25E-NBOMe&oldid=4310015"