Chemistry:25I-NBF

25I-NBF
Clinical data
ATC code	none;
Legal status
Legal status	BR: F2 ; DE: NpSG (Industrial and scientific use only) ; UK: Class A ;
Identifiers
	IUPAC name 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-fluorophenyl)methyl]ethan-1-amine;
CAS Number	919797-21-0 ;
PubChem CID	57469209;
ChemSpider	24751866 ;
UNII	MR8FRH5W3C;
Chemical and physical data
Formula	C17H19FINO2
Molar mass	415.247 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COc1cc(I)c(OC)cc1CCNCc2ccccc2F;
	InChI 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 ;
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Short description: Chemical compound

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-HT_2A receptor,^[1]^[2]^[3] with bias towards the β-arrestin 2 coupled signalling pathway.^[4] It has been studied in its ¹¹C radiolabelled form as a potential ligand for mapping the distribution of 5-HT_2A receptors in the brain, using positron emission tomography (PET).^[5]^[6]

Legality

25I-NBF is illegal in Hungary,^[7] Japan,^[8] Latvia,^[9] and Vermont.^[10]

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.^[11]

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.^[12]

Analogues and derivatives

Analogues and derivatives of 2C-I:

25I-NB*:

References

↑ "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.
↑ Braden MR (2007). Towards a biophysical understanding of hallucinogen action (Ph.D. thesis). Purdue University. ProQuest 304838368.
↑ "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.
↑ "Identification of psychedelic new psychoactive substances (NPS) showing biased agonism at the 5-HT_2AR through simultaneous use of β-arrestin 2 and miniGα_q bioassays". Biochemical Pharmacology 182: 114251. December 2020. doi:10.1016/j.bcp.2020.114251. PMID 32998000. https://biblio.ugent.be/publication/8687066.
↑ 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.
↑ "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.
↑ "A Magyarországon megjelent, a Kábítószer és Kábítószer-függőség Európai Megfigyelő Központjának Korai Jelzőrendszerébe (EMCDDA EWS) 2005 óta bejelentett ellenőrzött anyagok büntetőjogi vonatkozású besorolása" (in Hungarian). http://www.daath.hu/incoming/designer_jogi_lista_20150903_BSZKI_Daath_kieg.pdf.
↑ "指定薬物名称・構造式一覧（平成27年9月16日現在）" (in Japanese). 厚生労働省. 16 September 2015. http://www.mhlw.go.jp/seisakunitsuite/bunya/kenkou_iryou/iyakuhin/yakubuturanyou/dl/meisho.pdf.
↑ "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" (in Latvian). Ministry of Health of the Republic of Latvia. http://www.vm.gov.lv/images/userfiles/metodiskas_vadlinijas_080914.doc.
↑ "Regulated Drugs Rule". Vermont Department of Health. http://healthvermont.gov/regs/documents/regulated_drugs_rule_20160101.pdf.
↑ Ödman, Pär. "Gemensamma författningssamlingen avseende hälso- och sjukvård, socialtjänst, läkemedel, folkhälsa m.m." (in Swedish). Lakemedelsverket. https://lakemedelsverket.se/upload/lvfs/HSLF-FS/HSLFS-FS_2015_35.pdf.
↑ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014" (in en). http://www.legislation.gov.uk/uksi/2014/1106/made.

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[1] "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.

[2] Braden MR (2007). Towards a biophysical understanding of hallucinogen action (Ph.D. thesis). Purdue University. ProQuest 304838368.

[3] "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.

[4] "Identification of psychedelic new psychoactive substances (NPS) showing biased agonism at the 5-HT_2AR through simultaneous use of β-arrestin 2 and miniGα_q bioassays". Biochemical Pharmacology 182: 114251. December 2020. doi:10.1016/j.bcp.2020.114251. PMID 32998000. https://biblio.ugent.be/publication/8687066.

[5] 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.

[6] "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.

[7] "A Magyarországon megjelent, a Kábítószer és Kábítószer-függőség Európai Megfigyelő Központjának Korai Jelzőrendszerébe (EMCDDA EWS) 2005 óta bejelentett ellenőrzött anyagok büntetőjogi vonatkozású besorolása" (in Hungarian). http://www.daath.hu/incoming/designer_jogi_lista_20150903_BSZKI_Daath_kieg.pdf.

[8] "指定薬物名称・構造式一覧（平成27年9月16日現在）" (in Japanese). 厚生労働省. 16 September 2015. http://www.mhlw.go.jp/seisakunitsuite/bunya/kenkou_iryou/iyakuhin/yakubuturanyou/dl/meisho.pdf.

[9] "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" (in Latvian). Ministry of Health of the Republic of Latvia. http://www.vm.gov.lv/images/userfiles/metodiskas_vadlinijas_080914.doc.

[10] "Regulated Drugs Rule". Vermont Department of Health. http://healthvermont.gov/regs/documents/regulated_drugs_rule_20160101.pdf.

[11] Ödman, Pär. "Gemensamma författningssamlingen avseende hälso- och sjukvård, socialtjänst, läkemedel, folkhälsa m.m." (in Swedish). Lakemedelsverket. https://lakemedelsverket.se/upload/lvfs/HSLF-FS/HSLFS-FS_2015_35.pdf.

[12] "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014" (in en). http://www.legislation.gov.uk/uksi/2014/1106/made.

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v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-BZ 3C-E 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L -Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA Phenpromethamine PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D -Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D -DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L -DOPA (Levodopa) L -DOPS (Droxidopa) L -Phenylalanine L -Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101

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Clinical data

ATC code	none
Legal status
Legal status	BR: F2 DE: NpSG (Industrial and scientific use only) UK: Class A
Identifiers
IUPAC name 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-fluorophenyl)methyl]ethan-1-amine
CAS Number	919797-21-0^Y
PubChem CID	57469209
ChemSpider	24751866^Y
UNII	MR8FRH5W3C
Chemical and physical data
Formula	C₁₇H₁₉FINO₂
Molar mass	415.247 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES COc1cc(I)c(OC)cc1CCNCc2ccccc2F
InChI 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^Y Key:LPBKNBHMWRBPHT-UHFFFAOYSA-N^Y
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