Knowledge (XXG)

25I-NBF

Source 📝

Chemical compound
25I-NBF
Clinical data
ATC code
  • none
Legal status
Legal status
  • BR: Class F2 (Prohibited psychotropics)
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
Identifiers
  • 2-(4-iodo-2,5-dimethoxyphenyl)-N-ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H19FINO2
Molar mass415.247 g·mol
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
  • Key:LPBKNBHMWRBPHT-UHFFFAOYSA-N
  (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, with bias towards the β-arrestin 2 coupled signalling pathway. It has been studied in its C radiolabelled form as a potential ligand for mapping the distribution of 5-HT2A receptors in the brain, using positron emission tomography (PET).

Legality

25I-NBF is illegal in Hungary, Japan, Latvia, and Vermont.

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.

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.

Analogues and derivatives

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. hdl:1854/LU-8687066. PMID 32998000. S2CID 222150466. Archived from the original on 2024-01-08. Retrieved 2024-05-27.
  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). Archived (PDF) from the original on 2022-03-31. Retrieved 2015-10-15.
  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. Archived (PDF) from the original on 21 April 2022. 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). Archived from the original (PDF) on 2017-10-31. Retrieved 2017-04-21.
  13. "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Statutory Instruments 2014 No. 1106. www.legislation.gov.uk.
  14. "Explore N-(2C-I)-Fentanyl | PiHKAL · info". isomerdesign.com.
Psychedelics
(5-HT2A
agonists)
Benzofurans
Lyserg‐
amides
Phenethyl‐
amines
2C-x
25x-NBx
25x-NB
25x-NB3OMe
25x-NB4OMe
25x-NBF
25x-NBMD
25x-NBOH
25x-NBOMe
Atypical structures
25x-NMx
N-(2C)-fentanyl
3C-x
4C-x
DOx
HOT-x
MDxx
Mescaline (subst.)
TMAs
  • TMA
  • TMA-2
  • TMA-3
  • TMA-4
  • TMA-5
  • TMA-6
Others
Piperazines
Tryptamines
alpha-alkyltryptamines
x-DALT
x-DET
x-DiPT
x-DMT
x-DPT
Ibogaine-related
x-MET
x-MiPT
Others
Others
Dissociatives
(NMDAR
antagonists)
Arylcyclo‐
hexylamines
Ketamine-related
PCP-related
Others
Adamantanes
Diarylethylamines
Morphinans
Others
Deliriants
(mAChR
antagonists)
Others
Cannabinoids
(CB1 agonists)
Natural
Synthetic
AM-x
CP x
HU-x
JWH-x
Misc. designer cannabinoids
D2 agonists
GABAA
enhancers
Inhalants
(Mixed MOA)
κOR agonists
Oneirogens
Others
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
Phenethylamines


Stimulants: Phenylethanolamine

Amphetamines
Phentermines
Cathinones
Phenylisobutylamines
Phenylalkylpyrrolidines
Catecholamines
(and close relatives)
Miscellaneous

Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.

↑