25I-NBF

25I-NBF
Clinical data
ATC code	none;
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 ;
Chemical and physical data
Formula	C17H19FINO2
Molar mass	415.240 g/mol
3D model (Jmol)	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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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] 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).^[3]

Legality[edit]

25I-NBF is illegal in Hungary,^[4] Japan,^[5] Latvia,^[6] and Vermont.^[7]

25I-NBF is illegal in Sweden as of 26. January 2016.^[8]

References[edit]

^ Braden, MR; Parrish, JC; Naylor, JC; Nichols, DE (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.
^ Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007.
^ Ettrup, A.; Hansen, M.; Santini, M. A.; Paine, J.; Gillings, N.; Palner, M.; Lehel, S.; Herth, M. M.; Madsen, J.; et al. (2010). "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.
^ A Magyarországon megjelent, a Kábítószer és Kábítószer-függőség Európai Megfigyelő Központjának Korai Jelzőrendszerébe (EMCDDA EWS) 2005 óta bejelentett ellenőrzött anyagok büntetőjogi vonatkozású besorolása
^ "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.
^ Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem
^ "Regulated Drugs Rule" (PDF). Vermont Department of Health. Retrieved 14 October 2015.
^ "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015.

[1] Braden, MR; Parrish, JC; Naylor, JC; Nichols, DE (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] Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007.

[3] Ettrup, A.; Hansen, M.; Santini, M. A.; Paine, J.; Gillings, N.; Palner, M.; Lehel, S.; Herth, M. M.; Madsen, J.; et al. (2010). "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.

[4] A Magyarországon megjelent, a Kábítószer és Kábítószer-függőség Európai Megfigyelő Központjának Korai Jelzőrendszerébe (EMCDDA EWS) 2005 óta bejelentett ellenőrzött anyagok büntetőjogi vonatkozású besorolása

[5] "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.

[6] Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem

[7] "Regulated Drugs Rule" (PDF). Vermont Department of Health. Retrieved 14 October 2015.

[8] "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015.

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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-B-FLY βk-2C-B 2C-C 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-I 2C-N 2C-P 2C-SE 2C-T 2C-T-2 2C-T-4 2C-T-7 2C-T-8 2C-T-9 2C-T-13 2C-T-15 2C-T-16 2C-T-17 2C-T-21 2C-TFM 2C-YN 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 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 MDEA MDHMA MDMA MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DFMDA 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 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) Theodrenaline Thiamphenicol UWA-101

25I-NBF

Legality[edit]

See also[edit]

References[edit]

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Clinical data

ATC code	none
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
Chemical and physical data
Formula	C₁₇H₁₉FINO₂
Molar mass	415.240 g/mol
3D model (Jmol)	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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