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25B-NBOH

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25B-NBOH
Clinical data
Other names2C-B-NBOH; NBOH-2C-B; N-(2-Hydroxybenzyl)-4-bromo-2,5-dimethoxyphenethylamine
Drug classSerotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Legal status
Legal status
Identifiers
  • 2-({[2-(4-bromo-2,5-dimethoxyphenyl)ethyl]amino}methyl)phenol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H20BrNO3
Molar mass366.255 g·mol−1
3D model (JSmol)
  • BrC2=CC(=C(CCNCC1=C(C=CC=C1)O)C=C2OC)OC
  • InChI=1S/C17H20BrNO3/c1-21-16-10-14(18)17(22-2)9-12(16)7-8-19-11-13-5-3-4-6-15(13)20/h3-6,9-10,19-20H,7-8,11H2,1-2H3
  • Key:RSUNJYKZRKIBNB-UHFFFAOYSA-N

25B-NBOH, also known as N-(2-hydroxybenzyl)-4-bromo-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine, 2C, and N-benzylphenethylamine families related to 2C-B and 25B-NBOMe.[2][3] It has been sold and encountered as a novel designer drug.[2][4]

Interactions

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Pharmacology

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Pharmacodynamics

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25B-NBOH acts as a potent serotonin receptor agonist with similar affinity to the better-known compound 25B-NBOMe at 5-HT2A and 5-HT2C receptors with affinities (Ki) of 5.0 nM and 0.40 nM, respectively.[5][6][7][8][9][10] It fully substitutes for DOM in rodent drug discrimination tests, but with about 26-fold greater potency in comparison.[3] The drug was also 18-fold more potent in substituting for DOM than 25B-NBOMe in rodents.[3] In addition to its psychedelic-like effects, 25B-NBOH produces hypolocomotion in rodents, but with about 60% of the potency of DOM and about the same potency as 25B-NBOMe.[3] There was an 853-fold difference in its potency in the drug discrimination and hypolocomotion tests, which is described as unusual among psychedelics and warranting further investigation.[3]

Chemistry

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Synthesis

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The chemical synthesis of 25B-NBOH has been described.[5][6]

Analogues

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Analogues of 25B-NBOH include 25B-NBOMe, 25I-NBOH, 25C-NBOH, and 2C-B, among others.[2]

History

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25B-NBOH was first described in the scientific literature by Ralm Heim and colleagues by 2000.[11] It was first encountered and described as a novel designer drug by 2016.[4]

Society and culture

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Canada

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25B-NBOH is a controlled substance in Canada under phenethylamine blanket-ban language.[12]

Sweden

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The Riksdag added 25B-NBOH to Narcotic Drugs Punishments Act under Swedish Schedule I ("substances, plant materials and fungi which normally do not have medical use") as of January 26, 2016, published by Medical Products Agency (MPA) in regulation HSLF-FS 2015:35 listed as 25B-NBOH, and 2-([2-(4-bromo-2,5-dimetoxifenyl)etylamino]metyl)fenol.[13]

United Kingdom

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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.[14]

United States

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25B-NBOH is not an explicitly controlled substance in the United States.[15] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

See also

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References

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  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 (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  2. 1 2 3 Awuchi CG, Aja MP, Mitaki NB, Morya S, Amagwula IO, Echeta CK, et al. (2 February 2023). "New Psychoactive Substances: Major Groups, Laboratory Testing Challenges, Public Health Concerns, and Community-Based Solutions". Journal of Chemistry. 2023: 1–36. doi:10.1155/2023/5852315. ISSN 2090-9071.
  3. 1 2 3 4 5 Munir DD, Shetty RA, Gatch MB, Sumien N, Hill RD, Priddy JA, et al. (April 2025). "Locomotor and discriminative stimulus effects of NBOH hallucinogens in rodents". Behavioural Pharmacology. 36 (2–3): 107–114. doi:10.1097/FBP.0000000000000802. PMC 11884793. PMID 39642035.
  4. 1 2 "EMCDDA2017". isomerdesign.com.
  5. 1 2 Heim R (25 March 2003). "Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts" [Synthesis and pharmacology of potent 5-HT2A receptor agonists with an N-2-methoxybenzyl partial structure. Development of a new structure-activity concept.] (in German). diss.fu-berlin.de. Archived from the original on 2012-04-16. Retrieved 2013-05-10.
  6. 1 2 Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, et al. (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.
  7. ↑ 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.
  8. ↑ Ettrup A, Hansen M, Santini MA, Paine J, Gillings N, Palner M, et al. (April 2011). "Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT (2A) agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging. 38 (4): 681–693. doi:10.1007/s00259-010-1686-8. PMID 21174090. S2CID 12467684.
  9. ↑ Silva ME, Heim R, Strasser A, Elz S, Dove S (January 2011). "Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor". Journal of Computer-Aided Molecular Design. 25 (1): 51–66. Bibcode:2011JCAMD..25...51S. CiteSeerX 10.1.1.688.2670. doi:10.1007/s10822-010-9400-2. PMID 21088982. S2CID 3103050.
  10. ↑ Braden MR, Parrish JC, Naylor JC, Nichols DE (December 2006). "Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists". Molecular Pharmacology. 70 (6): 1956–1964. doi:10.1124/mol.106.028720. PMID 17000863. S2CID 15840304.
  11. ↑ Pertz HH, Heim R, Elz S (2000). "B 1.11. N-Benzylated phenylethanamines are highly potent partial agonists at 5-HT2A receptors". Arch. Pharm. Pharm. Med. Chem. 333 (Suppl 2): 1–84 (30). Archived from the original on 20 March 2025.
  12. ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
  13. ↑ "Läkemedelsverkets föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotik" [The Swedish Medicines Agency's regulations on amendments to the Swedish Medicines Agency's regulations (LVFS 2011: 10) on lists of drugs] (PDF). Läkemedelsverket. Archived from the original (PDF) on 2017-10-31. Retrieved 2017-04-21.
  14. ↑ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Statutory Instruments 2014 No. 1106. www.legislation.gov.uk.
  15. ↑ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026
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