Chemistry:25TFM-NBOMe

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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 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.

Interactions

Pharmacology

Pharmacodynamics

25TFM-NBOMe activities
Target Affinity (Ki, nM)
5-HT1A ND
5-HT1B ND
5-HT1D 1,817
5-HT1E ND
5-HT1F ND
5-HT2A 0.35–0.49 (Ki)
0.96–2.0 (EC50)
80–92% (Emax)
5-HT2B 1.1 (Ki)
ND (EC50)
ND (Emax)
5-HT2C 2.7 (Ki) (rat)
11.5 (EC50)
110% (Emax)
5-HT3 ND
5-HT4 ND
5-HT5A 8,128
5-HT6 23.4
5-HT7 5,974
α1A–α1D ND
α2A–α2C ND
β1–β3 ND
D1–D5 ND
H1–H4 ND
M1–M5 ND
I1 ND
σ1, σ2 ND
ORs ND
TAAR1 ND
SERT ND (Ki)
ND (IC50)
ND (EC50)
NET ND (Ki)
ND (IC50)
ND (EC50)
DAT 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: [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

Analogues

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

History

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

Canada

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


See also

  • 25-NB (psychedelics)

References

  1. ↑ 1.0 1.1 "Partial 5-HT2A-receptor agonists of the phenylethanamine series: effect of a trifluoromethyl substituent.". Arch. Pharm. Pharm. Med. Chem 333 (Supplement 2): 1.29. 2000. https://bitnest.netfirms.com/external/Arch.Pharm.Pharm.Med.Chem/333.S2.45. 
  2. ↑ 2.0 2.1 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).{{cite thesis}}: CS1 maint: unrecognized language (link)
  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. ↑ "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. 
  6. ↑ "Synthesis and Structure–Activity Relationships of N -Benzyl Phenethylamines as 5-HT 2A/2C Agonists". ACS Chemical Neuroscience 5 (3): 243–249. 19 March 2014. doi:10.1021/cn400216u. ISSN 1948-7193. PMID 24397362. 
  7. ↑ Silva M (2009). Theoretical study of the interaction of agonists with the 5-HT2A receptor (PhD thesis). Universität Regensburg.
  8. ↑ "Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor". Journal of Computer-aided Molecular Design 25 (1): 51–66. January 2011. doi:10.1007/s10822-010-9400-2. PMID 21088982. Bibcode: 2011JCAMD..25...51S. 
  9. ↑ "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. 
  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". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  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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