25TFM-NBOMe

Last updated

25TFM-NBOMe
2C-TFM-NBOMe.svg
Clinical data
Other namesNBOMe-2C-TFM; 2C-TFM-NBOMe; Cimbi-138
Drug class Serotonin 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
Formula C19H22F3NO3
Molar mass 369.384 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 Yes check.svgY
  • Key:FBHVTQIAHOTPAM-UHFFFAOYSA-N Yes check.svgY
   (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 ]

Contents

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 Tooltip half-maximal effective concentration)
80–92% (Emax Tooltip maximal efficacy)
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 Tooltip Trace amine-associated receptor 1ND
SERT Tooltip Serotonin transporterND (Ki)
ND (IC50 Tooltip half-maximal inhibitory concentration)
ND (EC50)
NET Tooltip Norepinephrine transporterND (Ki)
ND (IC50)
ND (EC50)
DAT Tooltip 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]

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

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 . [11]

See also

References

  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). Theoretical study of the interaction of agonists with the 5-HT2A receptor (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". 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.
  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. ↑ "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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