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'''25I-NBF''' ('''2C-I-NBF''', '''NBF-2C-I''', '''Cimbi-21''') is a derivative of the [[phenethylamine]] [[Psychedelic drug|hallucinogen]] [[2C-I]], which acts as a highly [[potency (pharmacology)|potent]] [[partial agonist]] for the [[human]] [[5-HT2A receptor|5-HT<sub>2A</sub>]] [[Receptor (biochemistry)|receptor]].<ref>{{cite journal | vauthors = Braden MR, Parrish JC, Naylor JC, Nichols DE | title = Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists | journal = Molecular Pharmacology | volume = 70 | issue = 6 | pages = 1956–64 | date = December 2006 | pmid = 17000863 | doi = 10.1124/mol.106.028720 | url = https://semanticscholar.org/paper/a8618f7d88ea8b7dfd27e0626b611d6b6bf4121d }}</ref><ref>{{cite thesis | first = Michael Robert | last = Braden | name-list-format = vanc | degree = Ph.D. | title = Towards a biophysical understanding of hallucinogen action. | publisher = Purdue University | date = 2007 | id = {{ProQuest|304838368}} }}</ref> It has been studied in its [[Carbon-11|<sup>11</sup>C]] [[isotopic labelling|radiolabelled]] form as a potential ligand for mapping the distribution of 5-HT<sub>2A</sub> receptors in the brain, using [[positron emission tomography]] (PET).<ref>{{cite thesis | vauthors = Hansen M | title = Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain. | degree = Ph.D. | publisher = University of Copenhagen | date = 2010-12-16 | doi = 10.13140/RG.2.2.33671.14245}}</ref><ref>{{cite journal | vauthors = Ettrup A, Hansen M, Santini MA, Paine J, Gillings N, Palner M, Lehel S, Herth MM, Madsen J, Kristensen J, Begtrup M, Knudsen GM | display-authors = 6 | title = Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT (2A) agonist PET tracers | journal = European Journal of Nuclear Medicine and Molecular Imaging | volume = 38 | issue = 4 | pages = 681–93 | date = April 2011 | pmid = 21174090 | doi = 10.1007/s00259-010-1686-8 }}</ref>
'''25I-NBF''' ('''2C-I-NBF''', '''NBF-2C-I''', '''Cimbi-21''') is a derivative of the [[phenethylamine]] [[Psychedelic drug|hallucinogen]] [[2C-I]], which acts as a highly [[potency (pharmacology)|potent]] [[partial agonist]] for the [[human]] [[5-HT2A receptor|5-HT<sub>2A</sub>]] [[Receptor (biochemistry)|receptor]].<ref>{{cite journal | vauthors = Braden MR, Parrish JC, Naylor JC, Nichols DE | title = Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists | journal = Molecular Pharmacology | volume = 70 | issue = 6 | pages = 1956–64 | date = December 2006 | pmid = 17000863 | doi = 10.1124/mol.106.028720 | url = https://semanticscholar.org/paper/a8618f7d88ea8b7dfd27e0626b611d6b6bf4121d }}</ref><ref>{{cite thesis | first = Michael Robert | last = Braden | name-list-format = vanc | degree = Ph.D. | title = Towards a biophysical understanding of hallucinogen action. | publisher = Purdue University | date = 2007 | id = {{ProQuest|304838368}} }}</ref><ref>{{cite journal | vauthors = Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, Kristensen JL | title = Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists | journal = ACS Chemical Neuroscience | volume = 5 | issue = 3 | pages = 243–9 | date = March 2014 | pmid = 24397362 | pmc = 3963123 | doi = 10.1021/cn400216u }}</ref> It has been studied in its [[Carbon-11|<sup>11</sup>C]] [[isotopic labelling|radiolabelled]] form as a potential ligand for mapping the distribution of 5-HT<sub>2A</sub> receptors in the brain, using [[positron emission tomography]] (PET).<ref>{{cite thesis | vauthors = Hansen M | title = Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain. | degree = Ph.D. | publisher = University of Copenhagen | date = 2010-12-16 | doi = 10.13140/RG.2.2.33671.14245}}</ref><ref>{{cite journal | vauthors = Ettrup A, Hansen M, Santini MA, Paine J, Gillings N, Palner M, Lehel S, Herth MM, Madsen J, Kristensen J, Begtrup M, Knudsen GM | display-authors = 6 | title = Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT (2A) agonist PET tracers | journal = European Journal of Nuclear Medicine and Molecular Imaging | volume = 38 | issue = 4 | pages = 681–93 | date = April 2011 | pmid = 21174090 | doi = 10.1007/s00259-010-1686-8 }}</ref>


==Legality==
==Legality==

Revision as of 10:14, 6 May 2020

25I-NBF
Clinical data
ATC code
  • none
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
Identifiers
  • 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-fluorophenyl)methyl]ethan-1-amine
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H19FINO2
Molar mass415.240 g/mol 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.[1][2][3] 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).[4][5]

Legality

25I-NBF is illegal in Hungary,[6] Japan,[7] Latvia,[8] and Vermont.[9]

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.[10]

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.[11]

Analogues and derivatives

Analogues and derivatives of 2C-I:

25I-NB*:

N-(2C)-fentanyl:

References

  1. ^ 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): 1956–64. doi:10.1124/mol.106.028720. PMID 17000863.
  2. ^ Braden, Michael Robert (2007). Towards a biophysical understanding of hallucinogen action (Ph.D. thesis). Purdue University. ProQuest 304838368. {{cite thesis}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  3. ^ 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): 243–9. doi:10.1021/cn400216u. PMC 3963123. PMID 24397362.
  4. ^ 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.
  5. ^ 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): 681–93. doi:10.1007/s00259-010-1686-8. PMID 21174090.
  6. ^ "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).
  7. ^ "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.
  8. ^ "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).
  9. ^ "Regulated Drugs Rule" (PDF). Vermont Department of Health. Retrieved 14 October 2015.
  10. ^ Ödman, Pär. "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). {{cite web}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  11. ^ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Statutory Instruments 2014 No. 1106. www.legislation.gov.uk.
  12. ^ "Explore N-(2C-I)-Fentanyl | PiHKAL · info". isomerdesign.com.
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