25I-NBF
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-fluorophenyl)methyl]ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H19FINO2
Molar mass415.247 g·mol−1
3D model (JSmol)
  • COc1cc(I)c(OC)cc1CCNCc2ccccc2F
  • InChI=1S/C17H19FINO2/c1-21-16-10-15(19)17(22-2)9-12(16)7-8-20-11-13-5-3-4-6-14(13)18/h3-6,9-10,20H,7-8,11H2,1-2H3 checkY
  • Key:LPBKNBHMWRBPHT-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

25I-NBF (2C-I-NBF, NBF-2C-I, Cimbi-21) is a derivative of the phenethylamine hallucinogen 2C-I, which acts as a highly potent partial agonist for the human 5-HT2A receptor,[2][3][4] with bias towards the β-arrestin 2 coupled signalling pathway.[5] It has been studied in its 11C radiolabelled form as a potential ligand for mapping the distribution of 5-HT2A receptors in the brain, using positron emission tomography (PET).[6][7]

Legality

25I-NBF is illegal in Hungary,[8] Japan,[9] Latvia,[10] and Vermont.[11]

Sweden

The Riksdag added 25I-NBF 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 25I-NBF, and 2-(4-jodo-2,5-dimetoxifenyl)-N-(2-fluorobensyl)etanamin.[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]

Analogues and derivatives

Analogues and derivatives of 2C-I:

25I-NB*:

N-(2C)-fentanyl:

  • N-(2C-I) fentanyl[14]

References

  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. ↑ 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.
  3. ↑ Braden MR (2007). Towards a biophysical understanding of hallucinogen action (Ph.D. thesis). Purdue University. ProQuest 304838368.
  4. ↑ Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, Kristensen JL (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.
  5. ↑ Pottie E, Dedecker P, Stove CP (December 2020). "Identification of psychedelic new psychoactive substances (NPS) showing biased agonism at the 5-HT2AR through simultaneous use of β-arrestin 2 and miniGαq bioassays". Biochemical Pharmacology. 182: 114251. doi:10.1016/j.bcp.2020.114251. PMID 32998000. S2CID 222150466.
  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. ↑ 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.
  8. ↑ "A Magyarországon megjelent, a Kábítószer és Kábítószer-függőség Európai Megfigyelő Központjának Korai Jelzőrendszerébe (EMCDDA EWS) 2005 óta bejelentett ellenőrzött anyagok büntetőjogi vonatkozású besorolása" [Criminal classification of controlled substances published in Hungary and notified to the European Monitoring Center for Drugs and Drug Addiction (EMCDDA EWS) since 2005] (PDF) (in Hungarian).
  9. ↑ "指定薬物名称・構造式一覧（平成27年9月16日現在）" (PDF) (in Japanese). 厚生労働省. 16 September 2015. Retrieved 8 October 2015.
  10. ↑ "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" [Regulations on Narcotic Drugs, Psychotropic Substances and Precursors Controlled in Latvia]. Ministry of Health of the Republic of Latvia (in Latvian). Archived from the original on 2016-03-04. Retrieved 2015-10-15.
  11. ↑ "Regulated Drugs Rule" (PDF). Vermont Department of Health. Archived from the original (PDF) on 5 June 2016. Retrieved 14 October 2015.
  12. ↑ Ödman P. "Gemensamma författningssamlingen avseende hälso- och sjukvård, socialtjänst, läkemedel, folkhälsa m.m." [Joint constitutional collection on health care, social services, pharmaceuticals, public health, etc.] (PDF). Lakemedelsverket (in Swedish).
  13. ↑ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". www.legislation.gov.uk.
  14. ↑ "Explore N-(2C-I)-Fentanyl | PiHKAL · info". isomerdesign.com.
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