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RU-28253

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RU-28253
Clinical data
Other namesRU28253; 5-MeO-THPI
Drug classNon-selective serotonin receptor agonist
ATC code
  • None
Identifiers
  • 5-methoxy-3-(1,2,3,6-tetrahydropyridin-5-yl)-1H-indole
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC14H16N2O
Molar mass228.295 g·mol−1
3D model (JSmol)
  • COC1=CC2=C(C=C1)NC=C2C3=CCCNC3
  • InChI=1S/C14H16N2O/c1-17-11-4-5-14-12(7-11)13(9-16-14)10-3-2-6-15-8-10/h3-5,7,9,15-16H,2,6,8H2,1H3
  • Key:WBJMGSVSSCEGFV-UHFFFAOYSA-N

RU-28253, also known as 5-MeO-THPI, is a non-selective serotonin receptor agonist of the tryptamine, 5-methoxytryptamine, and tetrahydropyridinylindole families.[1][2][3][4] It is a tetrahydropyridylindole and a conformationally constrained analogue of 5-MeO-DMT.[2][3]

The drug shows high affinity for the serotonin 5-HT1A receptor (Ki = 5.7 nM) and lower affinity for the serotonin 5-HT2A receptor (Ki = 230 nM).[2] Its affinities for these receptors were higher than those of dimethyltryptamine (DMT).[2] RU-28253 is described as a potent agonist of the serotonin 5-HT1 and 5-HT2 receptors,[5] including of the serotonin 5-HT1B receptor,[6] and is also an agonist of the serotonin 5-HT4 receptor.[3][7]

RU-28253 was first described in the scientific literature by 1983.[8][9][2]

See also

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References

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  1. ↑ Kitson SL (2007). "5-hydroxytryptamine (5-HT) receptor ligands". Current Pharmaceutical Design. 13 (25): 2621–2637. doi:10.2174/138161207781663000. PMID 17897004.
  2. 1 2 3 4 5 Taylor EW, Nikam S, Weck B, Martin A, Nelson D (October 1987). "Relative selectivity of some conformationally constrained tryptamine analogs at 5-HT1, 5-HT1A and 5-HT2 recognition sites". Life Sciences. 41 (16): 1961–1969. doi:10.1016/0024-3205(87)90749-1. PMID 3657392.
  3. 1 2 3 Dean RL (1999). Conformationally and rotationally restricted analogs of 5-hydroxytryptamine (Ph.D. thesis). University of Arizona. ProQuest 304510409. Retrieved 1 April 2025. Tetrahydropyridylindoles have been of interest since the initial reports showed that RU 24969 (6) and RU 28253 (7) had high potency as 5-HT agonists and were able to differentiate between certain 5-HT receptors (Euvard, 1980; Hunt, 1981). [...] RU 28253 acts as an agonist at the 5-HT4 receptor, having selective activity over RU 24969. [...]
  4. ↑ Nichols DE, Oberlender R, McKenna DJ (1991). "Stereochemical Aspects of Hallucinogenesis". In Watson RR (ed.). Biochemistry and Physiology of Substance Abuse. Vol. 3. Boca Raton, Fla.: CRC Press. pp. 1–39. ISBN 978-0-8493-4463-3. OCLC 26748320.
  5. ↑ Dahlgren T, Dean RL, Gharat LA, Johansson AM, Lambert G, Li HB, et al. (1995). "Synthesis and serotonin receptor binding properties of 5-substituted 3-(1′,2′,5′,6′-tetrahydropyridin-3′-yl) indoles". Bioorganic & Medicinal Chemistry Letters. 5 (24): 2963–2968. doi:10.1016/0960-894X(95)00534-8.
  6. ↑ Dumuis A, Bouhelal R, Sebben M, Cory R, Bockaert J (December 1988). "A nonclassical 5-hydroxytryptamine receptor positively coupled with adenylate cyclase in the central nervous system". Molecular Pharmacology. 34 (6): 880–887. doi:10.1016/S0026-895X(25)10130-2. PMID 2849052.
  7. ↑ Dumuis A, Ansanay H, Waeber C, Sebben M, Fagni L, Bockaert J (1997). "5-HT4 receptors". Pharmacochemistry Library. Vol. 27. Elsevier. pp. 261–308. doi:10.1016/s0165-7208(97)80017-7. ISBN 978-0-444-82041-9.
  8. ↑ Marrs TC (1983). "Poster Communications: Part I: The Actions of Three Mammalian Serotonin Receptor Agonists on Helix Central Neurones". British Journal of Pharmacology. 80 (Suppl): 494P–533P. PMC 2044929.
  9. ↑ Taylor EW (1985). The Development of Indoleamine Derivatives (Ph.D. thesis). University of Arizona. ProQuest 303387893. Retrieved 1 April 2025.
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