Chemistry:25B-NBOH

From HandWiki

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.[1][2] It has been sold and encountered as a novel designer drug.[1][3]

Interactions

Pharmacology

Pharmacodynamics

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.[4][5][6][7][8][9] It fully substitutes for DOM in rodent drug discrimination tests, but with about 26-fold greater potency in comparison.[2] The drug was also 18-fold more potent in substituting for DOM than 25B-NBOMe in rodents.[2] 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.[2] 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.[2]

Chemistry

Synthesis

The chemical synthesis of 25B-NBOH has been described.[4][5]

Analogues

Analogues of 25B-NBOH include 25B-NBOMe, 25I-NBOH, 25C-NBOH, and 2C-B, among others.[1]

History

25B-NBOH was first described in the scientific literature by Ralm Heim and colleagues by 2000.[10] It was first encountered and described as a novel designer drug by 2016.[3]

Society and culture

Canada

25B-NBOH is a controlled substance in Canada under phenethylamine blanket-ban language.[11]

Sweden

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.[12]

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.[13]


United States

25B-NBOH is not an explicitly controlled substance in the United States.[14] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

See also

References

  1. ↑ 1.0 1.1 1.2 "New Psychoactive Substances: Major Groups, Laboratory Testing Challenges, Public Health Concerns, and Community-Based Solutions". Journal of Chemistry 2023: 1–36. 2 February 2023. doi:10.1155/2023/5852315. ISSN 2090-9071. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 "Locomotor and discriminative stimulus effects of NBOH hallucinogens in rodents". Behavioural Pharmacology 36 (2–3): 107–114. April 2025. doi:10.1097/FBP.0000000000000802. PMID 39642035. 
  3. ↑ 3.0 3.1 "EMCDDA2017". https://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2016. 
  4. ↑ 4.0 4.1 "Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts." (in German). diss.fu-berlin.de. 25 March 2003. http://www.diss.fu-berlin.de/diss/receive/FUDISS_thesis_000000001221. 
  5. ↑ 5.0 5.1 "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. 
  6. ↑ 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.
  7. ↑ "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. April 2011. doi:10.1007/s00259-010-1686-8. PMID 21174090. 
  8. ↑ "Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor". Journal of Computer-Aided Molecular Design 25 (1): 51–66. January 2011. doi:10.1007/s10822-010-9400-2. PMID 21088982. Bibcode: 2011JCAMD..25...51S. 
  9. ↑ "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. December 2006. doi:10.1124/mol.106.028720. PMID 17000863. 
  10. ↑ "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). 2000. https://scholar.google.com/scholar?cluster=18169232060279208950. 
  11. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  12. ↑ "Läkemedelsverkets föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotik". Läkemedelsverket. https://lakemedelsverket.se/upload/lvfs/HSLF-FS/HSLFS-FS_2015_35.pdf. 
  13. ↑ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014" (in en). http://www.legislation.gov.uk/uksi/2014/1106/made. 
  14. ↑ 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:25B-NBOH&oldid=4582686"