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Pharmaceutical compound
1-Ethyl-6-hydroxytryptoline
Clinical data
Other names1-Et-6-OH-THβC; Compound 29[1]
Drug classSerotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonin 5-HT2C receptor agonist
ATC code
  • None
Identifiers
  • 1-ethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-6-ol
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC13H16N2O
Molar mass216.284 g·mol−1
3D model (JSmol)
  • CCC1C2=C(CCN1)C3=C(N2)C=CC(=C3)O
  • InChI=1S/C13H16N2O/c1-2-11-13-9(5-6-14-11)10-7-8(16)3-4-12(10)15-13/h3-4,7,11,14-16H,2,5-6H2,1H3
  • Key:JYRSBENZEDBDCG-UHFFFAOYSA-N

1-Ethyl-6-hydroxytryptoline (1-Et-6-OH-THβC) is a serotonin 5-HT2 receptor agonist of the β-carboline family related to tryptoline.[1] It is the 1-ethyl and 6-hydroxy derivative of tryptoline.[1]

The drug has been found to act as a potent agonist of the serotonin 5-HT2A and 5-HT2C receptors, with EC50Tooltip half-maximal effective concentration (EmaxTooltip maximal efficacy) values of 195 nM (85%) and 61 nM (98%) in terms of Gq-mediated calcium flux, respectively.[1] This is in notable contrast to other β-carbolines like harmine and harmaline, which are inactive as serotonin 5-HT2A receptor agonists.[3][4] It is also in apparent contrast to tryptoline, which shows very low affinity for the serotonin 5-HT2A receptor (Ki = 3,900 nM[5] and is inactive as an agonist of the serotonin 5-HT2B receptor (KB = >3,000 nM).[6]

The chemical synthesis of 1-ethyl-6-hydroxytryptoline has been described.[1]

1-Ethyl-6-hydroxytryptoline was described in the scientific literature by Meghan J. Orr and colleagues.[1]

See also

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References

[edit]
  1. 1 2 3 4 5 6 Orr MJ, Cao AB, Wang CT, Gaisin A, Csakai A, Friswold AP, et al. (April 2022). "Discovery of Highly Potent Serotonin 5-HT2 Receptor Agonists Inspired by Heteroyohimbine Natural Products". ACS Medicinal Chemistry Letters. 13 (4): 648–657. doi:10.1021/acsmedchemlett.1c00694. PMC 9014500. PMID 35450369. Aliphatic substitution at the 1 position gave rise to active compounds as well (26−29), though only 1-ethyl compound 29 had full agonist activity at both receptors
  2. ↑ Rolquin JD (3 May 2022). "Examining Ayahuasca Constituents at 5-HT2A Receptors in Search of Antidepressant Action". VCU Scholars Compass. Retrieved 7 April 2026.
  3. ↑ Grella B, Teitler M, Smith C, Herrick-Davis K, Glennon RA (December 2003). "Binding of beta-carbolines at 5-HT(2) serotonin receptors". Bioorganic & Medicinal Chemistry Letters. 13 (24): 4421–4425. doi:10.1016/j.bmcl.2003.09.027. PMID 14643338. [...] several β-carbolines, including harmaline (1) and its positional isomer 6-methoxyharmalan (4) substituted for the hallucinogenic (5-HT2A agonist) phenylalkylamine [DOM] in a drug discrimination task with rats trained to discriminate DOM from saline vehicle.10 However, neither harmaline (1; Ki=7790 nM) nor 6-methoxyharmalan (4; Ki=5600 nM) binds with high affinity at 5-HT2A receptors, and both were found to lack action as 5-HT2A agonists in a phosphoinositol (PI) hydrolysis assay.5,9 [...] At this time, it is not known if the actions of 1 and 4 in the PI hydrolysis assay reflect their low affinity, low efficacy, or whether the actions of the β-carbolines (in drug discrimination and/or other assays) is attributable to, or compromised by, their actions at other populations of receptors—particularly 5-HT receptors—or by possible interactions with the serotonin transporter.
  4. ↑ Bojarski AJ, Cegła MT, Charakchieva-Minol S, Mokrosz MJ, Maćkowiak M, Misztal S, et al. (April 1993). "Structure-activity relationship studies of CNS agents. Part 9: 5-HT1A and 5-HT2 receptor affinity of some 2- and 3-substituted 1,2,3,4-tetrahydro-beta-carbolines" (PDF). Die Pharmazie. 48 (4): 289–294. PMID 8321880. Archived from the original on 2026-04-04. Retrieved 2026-04-07.{{cite journal}}: CS1 maint: bot: original URL status unknown (link)
  5. ↑ Audia JE, Evrard DA, Murdoch GR, Droste JJ, Nissen JS, Schenck KW, et al. (July 1996). "Potent, selective tetrahydro-beta-carboline antagonists of the serotonin 2B (5HT2B) contractile receptor in the rat stomach fundus". Journal of Medicinal Chemistry. 39 (14): 2773–2780. doi:10.1021/jm960062t. PMID 8709108.
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