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Chemical compound

Pharmaceutical compound
25TFM-NBOMe
Clinical data
Other namesNBOMe-2C-TFM; 2C-TFM-NBOMe; Cimbi-138
Drug classSerotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
Identifiers
  • 2-(4-trifluoromethyl-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H22F3NO3
Molar mass369.384 g·mol−1
3D model (JSmol)
  • FC(F)(F)c1c(OC)cc(c(OC)c1)CCNCc2ccccc2OC
  • 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 checkY
  • Key:FBHVTQIAHOTPAM-UHFFFAOYSA-N checkY
  (verify)

25TFM-NBOMe (also known as NBOMe-2C-TFM, 2C-TFM-NBOMe, and Cimbi-138) is a derivative of the phenethylamine hallucinogen 2C-TFM, discovered by Ralf Heim at the Free University of Berlin by 2000.[1][2] It can be taken to produce psychedelic effects similar to 25I-NBOMe and 25D-NBOMe.[citation needed]

Interactions

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Pharmacology

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Pharmacodynamics

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25TFM-NBOMe activities
TargetAffinity (Ki, nM)
5-HT1AND
5-HT1BND
5-HT1D1,817
5-HT1END
5-HT1FND
5-HT2A0.35–0.49 (Ki)
0.96–2.0 (EC50Tooltip half-maximal effective concentration)
80–92% (EmaxTooltip maximal efficacy)
5-HT2B1.1 (Ki)
ND (EC50)
ND (Emax)
5-HT2C2.7 (Ki) (rat)
11.5 (EC50)
110% (Emax)
5-HT3ND
5-HT4ND
5-HT5A8,128
5-HT623.4
5-HT75,974
α1A–α1DND
α2A–α2CND
β1–β3ND
D1–D5ND
H1–H4ND
M1–M5ND
I1ND
σ1, σ2ND
ORsND
TAAR1Tooltip Trace amine-associated receptor 1ND
SERTTooltip Serotonin transporterND (Ki)
ND (IC50Tooltip half-maximal inhibitory concentration)
ND (EC50)
NETTooltip Norepinephrine transporterND (Ki)
ND (IC50)
ND (EC50)
DATTooltip Dopamine transporterND (Ki)
ND (IC50)
ND (EC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [3][4][5][6]

25TFM-NBOMe acts as a potent partial agonist for the serotonin 5-HT2A receptor, though its relative potency is disputed, with some studies finding it to be of lower potency than 25I-NBOMe,[7][8] while others show it to be of similar or higher potency,[9] possibly because of differences in the assay used.[10]

Chemistry

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Analogues

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Analogues of 25TFM-NBOMe include 2C-TFM, DOTFM, and TFMFly (DOTFM-FLY), among others.

History

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25TFM-NBOMe was first described in the scientific literature by Ralf Heim and colleagues at the Free University of Berlin by 2000.[1][2]

Society and culture

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25TFM-NBOMe is a controlled substance in Canada under phenethylamine blanket-ban language.[11]

United Kingdom

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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]

See also

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References

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  1. 1 2 Heim R, Pertz HH, Elz S (2000). "Partial 5-HT2A-receptor agonists of the phenylethanamine series: effect of a trifluoromethyl substituent". Arch. Pharm. Pharm. Med. Chem. 333 (Supplement 2): 1.29.
  2. 1 2 Heim R (2004). Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts [Synthesis and pharmacology of potent 5-HT2A receptor agonists with N-2-methoxybenzyl substructure. Development of a new structure-activity relationship] (PhD thesis) (in German).
  3. ↑ Ettrup A (2010). Serotonin receptor studies in the pig brain: pharmacological intervention and positron emission tomography tracer development (Ph.D. thesis). Faculty of Health Sciences, University of Copenhagen.
  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): 681–693. doi:10.1007/s00259-010-1686-8. PMID 21174090.
  6. ↑ Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, et al. (19 March 2014). "Synthesis and Structure–Activity Relationships of N -Benzyl Phenethylamines as 5-HT 2A/2C Agonists". ACS Chemical Neuroscience. 5 (3): 243–249. doi:10.1021/cn400216u. ISSN 1948-7193. PMC 3963123. PMID 24397362.
  7. ↑ Silva M (2009). (PhD thesis). Universität Regensburg.
  8. Silva ME, Heim R, Strasser A, Elz S, Dove S (January 2011). "Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor". . (1): 66. :. . :10.1007/s10822-010-9400-2. PMID 21088982. S2CID 3103050.
  9. ↑ 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.
  10. ↑ 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.
  11. ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
  12. ↑ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Statutory Instruments 2014 No. 1106. www.legislation.gov.uk.
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