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25TFM-NBOMe

Chemical compound

Chemical compound

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. It can be taken to produce psychedelic effects similar to 25I-NBOMe and 25D-NBOMe.

Interactions

Pharmacology

Pharmacodynamics

TargetAffinity (Ki, nM)
[5-HT1A](5-ht1a-receptor)ND
[5-HT1B](5-ht1b-receptor)ND
[5-HT1D](5-ht1d-receptor)1,817
[5-HT1E](5-ht1e-receptor)ND
[5-HT1F](5-ht1f-receptor)ND
[5-HT2A](5-ht2a-receptor)0.35–0.49 (Ki)
0.96–2.0 ()
80–92% ()
[5-HT2B](5-ht2b-receptor)1.1 (Ki)
ND (EC50)
ND (Emax)
[5-HT2C](5-ht2c-receptor)2.7 (Ki) (rat)
11.5 (EC50)
110% (Emax)
[5-HT3](5-ht3-receptor)ND
[5-HT4](5-ht4-receptor)ND
[5-HT5A](5-ht5a-receptor)8,128
[5-HT6](5-ht6-receptor)23.4
[5-HT7](5-ht7-receptor)5,974
α1A–α1DND
α2A–α2CND
β1–β3ND
D1–D5ND
H1–H4ND
M1–M5ND
I1ND
σ1, σ2ND
ORsND
ND
ND (Ki)
ND ()
ND (EC50)
ND (Ki)
ND (IC50)
ND (EC50)
ND (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:**

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, while others show it to be of similar or higher potency, possibly because of differences in the assay used.

History

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

Society and culture

Canada

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

United Kingdom

References

References

  1. (2004). "Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts".
  2. (2010). "Serotonin receptor studies in the pig brain: pharmacological intervention and positron emission tomography tracer development". Faculty of Health Sciences, University of Copenhagen.
  3. (2010-12-16). "Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain". University of Copenhagen.
  4. (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.
  5. (19 March 2014). "Synthesis and Structure–Activity Relationships of N -Benzyl Phenethylamines as 5-HT 2A/2C Agonists". ACS Chemical Neuroscience.
  6. (2009). "Theoretical study of the interaction of agonists with the 5-HT2A receptor.". Universität Regensburg.
  7. (January 2011). "Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor". Journal of Computer-aided Molecular Design.
  8. (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.
  9. (2010-12-16). "Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain.". University of Copenhagen.
  10. (2000). "Partial 5-HT2A-receptor agonists of the phenylethanamine series: effect of a trifluoromethyl substituent.". Arch. Pharm. Pharm. Med. Chem.
  11. "Controlled Drugs and Substances Act".
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25-nb-(psychedelics) 5-ht2a-agonists 5-ht2c-agonists trifluoromethyl-compounds
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