25T-NBOMe

25T-NBOMe
Clinical data
Other names2C-T-NBOMe; NBOMe-2C-T; N-(2-Methoxybenzyl)-4-methylthio-2,5-dimethoxyphenethylamine
Drug classSerotonin 5-HT2 receptor agonist; Possible serotonergic psychedelic; Possible hallucinogen
ATC code
  • None
Identifiers
IUPAC name
  • 2-(2,5-dimethoxy-4-methylsulfanylphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC19H25NO3S
Molar mass347.47 g·mol−1
3D model (JSmol)
SMILES
  • COC1=CC=CC=C1CNCCC2=CC(=C(C=C2OC)SC)OC
InChI
  • InChI=1S/C19H25NO3S/c1-21-16-8-6-5-7-15(16)13-20-10-9-14-11-18(23-3)19(24-4)12-17(14)22-2/h5-8,11-12,20H,9-10,13H2,1-4H3
  • Key:ZWPIZVVOKGWMFW-UHFFFAOYSA-N

25T-NBOMe, also known as 2C-T-NBOMe or NBOMe-2C-T as well as N-(2-methoxybenzyl)-4-methylthio-2,5-dimethoxyphenethylamine, is a serotonin 5-HT2 receptor agonist and possible serotonergic psychedelic of the phenethylamine, 2C, and 25-NB (NBOMe) families.[1][2] It is the NBOMe (N-(2-methoxybenzyl)) derivative of 2C-T.[1][2]

Interactions

Pharmacology

Pharmacodynamics

25T-NBOMe activities
TargetAffinity (Ki, nM)
5-HT1AND
5-HT1B3,385
5-HT1DND
5-HT1END
5-HT1FND
5-HT2A0.54 (Ki)
2.0–4.2 (EC50Tooltip half-maximal effective concentration)
86–179% (EmaxTooltip maximal efficacy)
5-HT2B0.91 (Ki)
ND (EC50)
ND (Emax)
5-HT2C7.4 (Ki) (rat)
21.4 (EC50)
103% (Emax)
5-HT3ND
5-HT4ND
5-HT5AND
5-HT6117
5-HT7ND
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][2][4]

25T-NBOMe acts as a potent agonist of the serotonin 5-HT2A and 5-HT2C receptors and also shows interactions with certain other targets, such as the serotonin 5-HT2B receptor.[1][2]

History

25T-NBOMe was first described in the scientific literature by 2010.[1]

See also

References

  1. 1 2 3 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.
  2. 1 2 3 4 Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, et al. (March 2014). "Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists". ACS Chemical Neuroscience. 5 (3): 243–249. doi:10.1021/cn400216u. PMC 3963123. PMID 24397362.
  3. ↑ 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.
  4. ↑ Pottie E, Poulie CB, Simon IA, Harpsøe K, D'Andrea L, Komarov IV, et al. (August 2023). "Structure-Activity Assessment and In-Depth Analysis of Biased Agonism in a Set of Phenylalkylamine 5-HT2A Receptor Agonists". ACS Chem Neurosci. 14 (15): 2727–2742. doi:10.1021/acschemneuro.3c00267. PMC 10401645. PMID 37474114.


This article is issued from WikiProjectMed. The text is available under Creative Commons Attribution-ShareAlike License unless otherwise noted. Additional terms may apply for the media files.