Chemistry:25H-NBOMe

From HandWiki

25H-NBOMe, also known as NBOMe-2C-H, is a derivative of the phenethylamine hallucinogen 2C-H, which acts as a highly potent full agonist for the human 5-HT2A receptor.[1]

Use and effects

The active dose range of 25H-NBOMe in humans has not been reported and hence is unknown.[2] This is in notable contrast to many other NBOMe drugs.[2]

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

25H-NBOMe activities
Target Affinity (Ki, nM)
5-HT1A 4,520–6,973 (Ki)
28,400 (EC50)
52% (Emax)
5-HT1B ND
5-HT1D ND
5-HT1E ND
5-HT1F ND
5-HT2A 2.83–49.4 (Ki)
11.0–490 (EC50)
38–144% (Emax)
5-HT2B 62.9 (Ki)
340–463 (EC50)
11–38% (Emax)
5-HT2C 16.4–130 (Ki)
13.8 (EC50)
96% (Emax)
5-HT3 ND
5-HT4 ND
5-HT5A ND
5-HT6 ND
5-HT7 ND
α1A 550
α1B, α1D ND
α2A 530
α2B, α2C ND
β1–β3 ND
D1 14,000
D2 7,700
D3 20,000
D4, D5 ND
H1 4,100
H2–H4 ND
M1–M5 ND
I1 ND
σ1, σ2 ND
MOR ND
DOR ND
KOR ND
TAAR1 >20,000 (Ki) (mouse)
1,400–1,500 (Ki) (rat)
6,100 (EC50) (mouse)
3,000 (EC50) (rat)
>10,000 (EC50) (human)
53% (Emax) (mouse)
37% (Emax) (rat)
SERT 2,220–2,300 (Ki)
2,080–12,000 (IC50)
IA (EC50)
NET 5,500–16,300 (Ki)
3,650–10,000 (IC50)
IA (EC50)
DAT 35,000–81,400 (Ki)
120,000 (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: [3][4][5][6][7][8]
[9][10][11][12][13][14]

25H-NBOMe acts as an agonist of the serotonin 5-HT2 receptors.[15][5]

Its affinity for the serotonin 5-HT2A receptor (Ki = 2.83 nM) was 133-fold higher than that of 2C-H and 24-fold higher than that of 25H-NB (N-benzyl-2C-H), whereas it was 4-fold lower than that of 2C-I and 64-fold lower than that of 25I-NBOMe.[5] In terms of activational potency at the receptor, the drug's potency (EC50 = 15.3 nM) was 67-fold higher than that of 2C-H, whereas it was 6-fold lower than that of 2C-I and 35-fold lower than that of 25I-NBOMe.[5] Hence, unlike other NBOMe drugs, 25H-NBOMe appears to have affinity and activational potency at the serotonin 5-HT2A receptor more in line with the 2C psychedelics like 2C-I and much lower than NBOMe drugs like 25I-NBOMe.[5]

25H-NBOMe produces hyperlocomotion, a stimulant-like effect, and the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[9][15][16] Its potency in inducing the head-twitch response was variably lower than that of other NBOMe drugs like 25I-NBOMe and 25B-NBOMe.[15][9] Conversely, its potency in inducing hyperlocomotion was about the same as that of 25I-NBOMe and 25C-NBOMe.[15] The drug has also been found to produce antidepressant-like effects in rodents.[16] 25H-NBOMe has shown reinforcing effects in rodents.[15][17] This included conditioned place preference (CPP) and self-administration.[15][17]

History

25H-NBOMe was first described in the scientific literature by Ralf Heim at the Free University of Berlin by 2003.[4]

Society and culture

Canada

25H-NBOMe is a controlled substance in Canada under phenethylamine blanket-ban language.[18]

Sweden

The Riksdag added 25H-NBOMe to Narcotic Drugs Punishments Act under swedish schedule I ("substances, plant materials and fungi which normally do not have medical use") as of August 1, 2013, published by Medical Products Agency (MPA) in regulation LVFS 2013:15 listed as 25H-NBOMe, and 2-(2,5-dimetoxifenyl)-N-(2-metoxibensyl)etanamin.[19]

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.[20]


United States

25H-NBOMe is not an explicitly controlled substance in the United States.[21] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

See also

Notes

References

  1. ↑ "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. 
  2. ↑ 2.0 2.1 "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.". 
  3. ↑ "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=14683&KisResultsSearch%5Binput_citations%5D=&KisResultsSearch%5Binput_citations%5D%5B%5D=2187&KisResultsSearch%5BsearchType%5D=&KisResultsSearch%5Bki_val_from%5D=&KisResultsSearch%5Bki_val_to%5D=&KisResultsSearch%5Bcustom_ki_val%5D=. 
  4. ↑ 4.0 4.1 Heim R (2004). Development of a new structure-activity conceptSynthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2 -Methoxybenzyl-Partialstruktur: Entwicklung eines neuen Struktur-Wirkungskonzepts (PDF). Universitätsbibliothek (Thesis). Freie Universität Berlin. doi:10.17169/refubium-16193. Retrieved 20 June 2025.
  5. ↑ 5.0 5.1 5.2 5.3 5.4 "Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists". Mol Pharmacol 70 (6): 1956–1964. December 2006. doi:10.1124/mol.106.028720. PMID 17000863. https://web.archive.org/web/20240416120352/https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=bfd0315d3e9117b10ad2e6719655db0c22a18711. 
  6. ↑ Braden MR (2007). Towards a biophysical understanding of hallucinogen action (Ph.D. thesis). Purdue University. ProQuest 304838368.
  7. ↑ Silva M (2009). Theoretical study of the interaction of agonists with the 5-HT2A receptor (PhD.). Universität Regensburg. Table 5.1: Agonistic potency (pEC50) and intrinsic activity (Emax) of 5-HT2AR partial agonistic arylethylamines (indole, methoxybenzene and quinazolinedione derivatives) used in the study. [...] [Compound] 229 [...]
  8. ↑ "Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor". J Comput Aided Mol Des 25 (1): 51–66. January 2011. doi:10.1007/s10822-010-9400-2. PMID 21088982. Bibcode: 2011JCAMD..25...51S. 
  9. ↑ 9.0 9.1 9.2 "Caracterización Farmacológica In Vitro e In Vivo del Agonista Serotoninérgico 5-HT2 Superpotente 25B-NBOMe: Modulación de Sus Efectos Inducida por Bromación Aromática" (in es). XXXVI Congreso Anual de la Sociedad de Farmacología de Chile. 2014. doi:10.13140/2.1.4332.8322. https://bitnest.netfirms.com/external/10.13140/2.1.4332.8322. Retrieved 20 June 2025. 
  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. ↑ "Serotonin 2A Receptor (5-HT2AR) Activation by 25H-NBOMe Positional Isomers: In Vitro Functional Evaluation and Molecular Docking". ACS Pharmacol Transl Sci 4 (2): 479–487. April 2021. doi:10.1021/acsptsci.0c00189. PMID 33860178. 
  14. ↑ "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. 
  15. ↑ 15.0 15.1 15.2 15.3 15.4 15.5 "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. 
  16. ↑ 16.0 16.1 "Psychoactive substances 25H-NBOMe and 25H-NBOH induce antidepressant-like behavior in male rats". Eur J Pharmacol 955. September 2023. doi:10.1016/j.ejphar.2023.175926. PMID 37479015. 
  17. ↑ 17.0 17.1 "Rewarding and Reinforcing Effects of 25H-NBOMe in Rodents". Brain Sci 12 (11): 1490. November 2022. doi:10.3390/brainsci12111490. PMID 36358416. 
  18. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  19. ↑ "Läkemedelsverkets föreskrifter - LVFS och HSLF-FS;Läkemedelsverket/Swedish Medical Products Agency". https://lakemedelsverket.se/upload/lvfs/LVFS_2013-15.pdf. 
  20. ↑ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014" (in en). http://www.legislation.gov.uk/uksi/2014/1106/made. 
  21. ↑ 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 



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