25TFM-NBOMe

25TFM-NBOMe
Identifiers
	IUPAC name 2-(4-trifluoromethyl-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine;
CAS Number	1027161-33-6 ;
PubChem CID	10067667;
ChemSpider	8243207 ;
UNII	X3V8LI2TUV;
CompTox Dashboard (EPA)	DTXSID40435135 ;
Chemical and physical data
Formula	C19H22F3NO3
Molar mass	369.384 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES FC(F)(F)c1c(OC)cc(c(OC)c1)CCNCc2ccccc2OC;
	InChI InChI=1S/C19H22F3NO3/c1-24-16-7-5-4-6-14(16)12-23-9-8-13-10-18(26-3)15(19(20,21)22)11-17(13)25-2/h4-7,10-11,23H,8-9,12H2,1-3H3 ; Key:FBHVTQIAHOTPAM-UHFFFAOYSA-N ;
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25TFM-NBOMe (also known as NBOMe-2C-TFM, 2C-TFM-NBOMe, and Cimbi-138) is a derivative of the phenethylamine hallucinogen 2C-TFM, discovered in 2004 by Ralf Heim at the Free University of Berlin.^[1] It acts as a potent partial agonist for the 5HT_2A receptor, though its relative potency is disputed, with some studies finding it to be of lower potency than 25I-NBOMe,^[2]^[3] while others show it to be of similar or higher potency,^[4] possibly because of differences in the assay used.^[5] 2C-TFM-NB2OMe can be taken to produce psychedelic effects similar to 2C-I-NB2OMe and 2C-D-NB2OMe.

Legality[]

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.^[6]

References[]

^ Ralf Heim PhD. Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts. (German)
^ Maria Silva PhD. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Universität Regensburg, 2009.
^ Silva ME, Heim R, Strasser A, Elz S, Dove S (January 2011). "Theoretical studies on the interaction of partial agonists with the 5-HT(2A) receptor". Journal of Computer-aided Molecular Design. 25 (1): 51–66. Bibcode:2011JCAMD..25...51S. CiteSeerX 10.1.1.688.2670. doi:10.1007/s10822-010-9400-2. PMID 21088982. S2CID 3103050.
^ 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. S2CID 12467684.
^ 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.
^ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". www.legislation.gov.uk.

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[1] Ralf Heim PhD. Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts. (German)

[2] Maria Silva PhD. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Universität Regensburg, 2009.

[pmid21088982-3] Silva ME, Heim R, Strasser A, Elz S, Dove S (January 2011). "Theoretical studies on the interaction of partial agonists with the 5-HT(2A) receptor". Journal of Computer-aided Molecular Design. 25 (1): 51–66. Bibcode:2011JCAMD..25...51S. CiteSeerX 10.1.1.688.2670. doi:10.1007/s10822-010-9400-2. PMID 21088982. S2CID 3103050.

[4] 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. S2CID 12467684.

[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] "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". www.legislation.gov.uk.

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v t Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-C 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-O 2C-O-4 2C-P 2C-SE 2C-T 2C-T-2 2C-T-3 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-19 2C-T-21 2C-T-28 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 Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 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 ZDCM-04 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 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 Venlafaxine

25TFM-NBOMe

Contents

Legality[]

United Kingdom[]

See also[]

References[]

Identifiers

IUPAC name 2-(4-trifluoromethyl-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
CAS Number	1027161-33-6^Y
PubChem CID	10067667
ChemSpider	8243207^Y
UNII	X3V8LI2TUV
CompTox Dashboard (EPA)	DTXSID40435135
Chemical and physical data
Formula	C₁₉H₂₂F₃NO₃
Molar mass	369.384 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES FC(F)(F)c1c(OC)cc(c(OC)c1)CCNCc2ccccc2OC
InChI InChI=1S/C19H22F3NO3/c1-24-16-7-5-4-6-14(16)12-23-9-8-13-10-18(26-3)15(19(20,21)22)11-17(13)25-2/h4-7,10-11,23H,8-9,12H2,1-3H3^Y Key:FBHVTQIAHOTPAM-UHFFFAOYSA-N^Y
^NY (what is this?)