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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 451565266
| verifiedrevid = 451565266
| IUPAC_name = 2-(4-iodo-2,5-dimethoxyphenyl)-''N''-[(2-fluorophenyl)methyl]ethanamine
| IUPAC_name = 2-(4-iodo-2,5-dimethoxyphenyl)-''N''-[(2-fluorophenyl)methyl]ethan-1-amine
| image = 25i-NBF.svg
| image = 25i-NBF.svg
| width = 200
| width = 200
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| pregnancy_category =
| pregnancy_category =
| routes_of_administration =
| routes_of_administration =
| legal_BR = F2
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-07-25}}</ref>
| legal_DE = NpSG
| legal_UK = Class A


<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
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<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 919797-21-0
| CAS_number = 919797-21-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = MR8FRH5W3C
| CAS_supplemental =
| CAS_supplemental =
| ATC_prefix = none
| ATC_prefix = none
| PubChem =
| PubChem = 57469209
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 24751866
| ChemSpiderID = 24751866
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<!--Chemical data-->
<!--Chemical data-->
| C=17 | H=19 | F=1 | I=1 | N=1 | O=2
| C=17 | H=19 | F=1 | I=1 | N=1 | O=2
| molecular_weight = 415.240 g/mol
| smiles = COc1cc(I)c(OC)cc1CCNCc2ccccc2F
| smiles = COc1cc(I)c(OC)cc1CCNCc2ccccc2F
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
Line 35: Line 43:
}}
}}


'''25I-NBF''' ('''2C-I-NBF''', '''NBF-2C-I''', '''Cimbi-21''') is a derivative of the [[phenethylamine]] [[psychedelic|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 | last1 = Braden | first1 = MR | last2 = Parrish | first2 = JC | last3 = Naylor | first3 = JC | last4 = Nichols | first4 = 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 | year = 2006 | pmid = 17000863 | doi = 10.1124/mol.106.028720 }}</ref><ref>[http://proquest.umi.com/pqdlink?Ver=1&Exp=01-23-2014&FMT=7&DID=1417800971&RQT=309&attempt=1&cfc=1 Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007.]</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 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 = 1956–1964 | date = December 2006 | pmid = 17000863 | doi = 10.1124/mol.106.028720 | s2cid = 15840304 }}</ref><ref>{{cite thesis | first = Michael Robert | last = Braden | name-list-style = 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 = 243–249 | date = March 2014 | pmid = 24397362 | pmc = 3963123 | doi = 10.1021/cn400216u }}</ref> with bias towards the [[Arrestin beta 2|β-arrestin 2]] coupled signalling pathway.<ref>{{cite journal | vauthors = Pottie E, Dedecker P, Stove CP | title = Identification of psychedelic new psychoactive substances (NPS) showing biased agonism at the 5-HT<sub>2A</sub>R through simultaneous use of β-arrestin 2 and miniGα<sub>q</sub> bioassays | journal = Biochemical Pharmacology | volume = 182 | pages = 114251 | date = December 2020 | pmid = 32998000 | doi = 10.1016/j.bcp.2020.114251 | s2cid = 222150466 | url = https://biblio.ugent.be/publication/8687066 | hdl = 1854/LU-8687066 | hdl-access = free | access-date = 2024-05-27 | archive-date = 2024-01-08 | archive-url = https://web.archive.org/web/20240108072825/https://biblio.ugent.be/publication/8687066 | url-status = live }}</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 = 681–693 | date = April 2011 | pmid = 21174090 | doi = 10.1007/s00259-010-1686-8 | s2cid = 12467684 }}</ref>


== See also ==
==Legality==
25I-NBF is illegal in Hungary,<ref>{{cite web | url = http://www.daath.hu/incoming/designer_jogi_lista_20150903_BSZKI_Daath_kieg.pdf | title = A Magyarországon megjelent, a Kábítószer és Kábítószer-függőség Európai Megfigyelő Központjának Korai Jelzőrendszerébe (EMCDDA EWS) 2005 óta bejelentett ellenőrzött anyagok büntetőjogi vonatkozású besorolása | trans-title = Criminal classification of controlled substances published in Hungary and notified to the European Monitoring Center for Drugs and Drug Addiction (EMCDDA EWS) since 2005 | language = Hungarian | access-date = 2015-10-15 | archive-date = 2022-03-31 | archive-url = https://web.archive.org/web/20220331185627/http://www.daath.hu/incoming/designer_jogi_lista_20150903_BSZKI_Daath_kieg.pdf | url-status = live }}</ref> Japan,<ref>{{cite web | url=http://www.mhlw.go.jp/seisakunitsuite/bunya/kenkou_iryou/iyakuhin/yakubuturanyou/dl/meisho.pdf | title=指定薬物名称・構造式一覧（平成27年9月16日現在） | publisher=厚生労働省 | date=16 September 2015 | language=Japanese | access-date=8 October 2015 | archive-date=21 April 2022 | archive-url=https://web.archive.org/web/20220421122530/https://www.mhlw.go.jp/seisakunitsuite/bunya/kenkou_iryou/iyakuhin/yakubuturanyou/dl/meisho.pdf | url-status=live }}</ref> Latvia,<ref>{{cite web | url = http://www.vm.gov.lv/images/userfiles/metodiskas_vadlinijas_080914.doc | title = Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem | trans-title = Regulations on Narcotic Drugs, Psychotropic Substances and Precursors Controlled in Latvia | language = Latvian | work = Ministry of Health of the Republic of Latvia | access-date = 2015-10-15 | archive-date = 2016-03-04 | archive-url = https://web.archive.org/web/20160304200229/http://www.vm.gov.lv/images/userfiles/metodiskas_vadlinijas_080914.doc | url-status = dead }}</ref> and Vermont.<ref>{{cite web | url=http://healthvermont.gov/regs/documents/regulated_drugs_rule_20160101.pdf | title=Regulated Drugs Rule | publisher=Vermont Department of Health | access-date=14 October 2015 | archive-date=5 June 2016 | archive-url=https://web.archive.org/web/20160605063259/http://healthvermont.gov/regs/documents/regulated_drugs_rule_20160101.pdf | url-status=dead }}</ref>
* [[2CBCB-NBOMe]] (NBOMe-TCB-2)

* [[2CBFly-NBOMe]] (NBOMe-2CB-Fly)
===Sweden===
* [[2C-C-NBOMe]] (NBOMe-2CC)
[[Riksdag|The Riksdag]] added 25I-NBF to [[:sv:Narkotikastrafflagen|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 (Sweden)|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'''.<ref>{{cite web | first = Pär | last = Ödman | name-list-style = vanc | title = Gemensamma författningssamlingen avseende hälso- och sjukvård, socialtjänst, läkemedel, folkhälsa m.m. | trans-title = Joint constitutional collection on health care, social services, pharmaceuticals, public health, etc. | url = https://lakemedelsverket.se/upload/lvfs/HSLF-FS/HSLFS-FS_2015_35.pdf | work = Lakemedelsverket | language = Swedish | access-date = 2017-04-21 | archive-date = 2017-10-31 | archive-url = https://web.archive.org/web/20171031000431/https://lakemedelsverket.se/upload/lvfs/HSLF-FS/HSLFS-FS_2015_35.pdf | url-status = dead }}</ref>
* [[25B-NBOMe]] (NBOMe-2CB)

* [[25I-NBOMe]] (NBOMe-2CI)
===United Kingdom===
* [[25I-NBMD]] (NBMD-2CI)
{{N-benzylphenethylamine-Legality-United Kingdom}}
* [[25I-NBOH]] (NBOH-2CI)

==Analogues and derivatives==
{{2C-I analogues and derivatives}}


== References ==
== References ==
{{Reflist}}
{{Reflist}}


{{Serotonergics}}
{{Hallucinogens}}
{{Serotonin receptor modulators}}
{{Phenethylamines}}


[[Category:Psychedelic phenethylamines]]
[[Category:25-NB (psychedelics)]]
[[Category:Organofluorides]]
[[Category:Designer drugs]]
[[Category:Organoiodides]]
[[Category:2-Fluorophenyl compounds]]
[[Category:Phenol ethers]]
[[Category:Iodobenzene derivatives]]

Latest revision as of 09:09, 5 September 2024

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

[edit]

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

Sweden

[edit]

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

[edit]

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

[edit]

Analogues and derivatives of 2C-I:

25I-NB*:

N-(2C)-fentanyl:

References

[edit]
  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.
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