Jump to content

NEtPhOH-THPI

Add links
From Wikipedia, the free encyclopedia

NEtPhOH-THPI
Clinical data
Other namesN′-(2-Hydroxyphenethyl)-THPI; Compound 24c; 3-(1-(2-Hydroxyphenylethyl)-1,2,3,6-tetrahydropyridin-5-yl)-1H-indole
Drug classSerotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • 2-{2-[5-(1H-indol-3-yl)-3,6-dihydropyridin-1(2H)-yl]ethyl}phenol
Chemical and physical data
FormulaC21H22N2O
Molar mass318.420 g·mol−1
3D model (JSmol)
  • O([H])C1C=CC=CC=1CCN1CC(C2C3C(=CC=CC=3)N([H])C=2)=CCC1
  • InChI=1S/C21H22N2O/c24-21-10-4-1-6-16(21)11-13-23-12-5-7-17(15-23)19-14-22-20-9-3-2-8-18(19)20/h1-4,6-10,14,22,24H,5,11-13,15H2
  • Key:FGMLLLJKETXMGK-UHFFFAOYSA-N

NEtPhOH-THPI, also known as N′-(2-hydroxyphenethyl)-THPI, is a serotonin 5-HT2 receptor agonist and possible serotonergic psychedelic of the tetrahydropyridinylindole (THPI) family related to psychedelic tryptamines.[1] It is a cyclized tryptamine with an NBOMe-like substitution.[1]

The drug is a potent and high-efficacy partial agonist of the serotonin 5-HT2A receptor.[1] Its affinity (Ki) for the receptor was 8.58 nM and its EC50Tooltip half-maximal effective concentration and EmaxTooltip maximal efficacy values were 20.7 nM (66.5%) for Gq signaling and 58.4 nM (80.7%) for β-arrestin2 signaling.[1] NEtPhOH-THPI is also a potent near-full agonist of the serotonin 5-HT2B receptor (EC50 = 7.94 nM; Emax = 88.9%) and a lower-potency full agonist of the serotonin 5-HT2C receptor (EC50 = 263 nM; Emax = 105.1%).[1] It is a weak serotonin reuptake inhibitor (IC50Tooltip half-maximal inhibitory concentration = 1,288 nM) as well.[1]

NEtPhOH-THPI induced the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[1] It produced the head-twitch response at a dose of 3 mg/kg in mice but not at a dose of 1 mg/kg or 10 mg/kg.[1] The drug produced about half the maximal number of head twitches as LSD.[1] The preclinical pharmacokinetics of NEtPhOH-THPI via intraperitoneal injection have been studied.[1]

NEtPhOH-THPI was first described in the scientific literature by Rongyan Li and colleagues by 2025.[1] A close non-hallucinogenic pyrrolopyridine analogue with antidepressant-like effects in rodents was also reported.[1] The chemical syntheses of both this compound and NEtPhOH-THPI were described.[1]

See also

[edit]

References

[edit]
  1. ^ a b c d e f g h i j k l m Li R, Yan H, Chen Y, Liu Y, Tang L, Yu J, et al. (October 2025). "Structure-Guided Design of Novel 5-HT2A Partial Agonists as Psychedelic Analogues with Antidepressant Effects". Journal of Medicinal Chemistry. 68 (20): 21683–21700. doi:10.1021/acs.jmedchem.5c02045. PMID 41087124.
[edit]
Retrieved from "https://en.wikipedia.org/w/index.php?title=NEtPhOH-THPI&oldid=1338425897"