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5-MeO-IsoqT

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5-MeO-IsoqT
Clinical data
Other names5-MeO-desethylisoquinuclidineT; Desethyl-17,18-secoibogaine
ATC code
  • None
Identifiers
  • 3-[2-(2-azabicyclo[2.2.2]octan-2-yl)ethyl]-5-methoxy-1H-indole
PubChem CID
ChemSpider
Chemical and physical data
FormulaC18H24N2O
Molar mass284.403 g·mol−1
3D model (JSmol)
  • COC1=CC2=C(C=C1)NC=C2CCN3CC4CCC3CC4
  • InChI=1S/C18H24N2O/c1-21-16-6-7-18-17(10-16)14(11-19-18)8-9-20-12-13-2-4-15(20)5-3-13/h6-7,10-11,13,15,19H,2-5,8-9,12H2,1H3
  • Key:ACNCVCCDIUQDHS-UHFFFAOYSA-N

5-MeO-IsoqT, also known as 5-MeO-desethylisoquinuclidineT or as desethyl-17,18-secoibogaine, is a tryptamine derivative and a deconstructed and simplified analogue of ibogaine.[1] It is a derivative of ibogaine lacking the tetrahydroazepine ring but with the isoquinuclidine ring retained.[1] Similarly to ibogaine and noribogaine, but unlike structurally related tryptamines like 5-MeO-DMT and 5-MeO-pip-T, 5-MeO-IsoqT is said to have insignificant activity as an agonist of the serotonin 5-HT1A and 5-HT2A receptors.[1] 5-MeO-IsoqT was described in the scientific literature by Dalibor Sames and colleagues in 2024.[1] Other closely related isoquinuclidine-tryptamines have also been described by David E. Olson and colleagues in 2021, for instance the ethyl-conserved 5-hydroxy and 5-methoxy analogues.[2]

See also

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References

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  1. ^ a b c d Warren AL, Lankri D, Cunningham MJ, Serrano IC, Parise LF, Kruegel AC, et al. (June 2024). "Structural pharmacology and therapeutic potential of 5-methoxytryptamines". Nature. 630 (8015): 237–246. Bibcode:2024Natur.630..237W. doi:10.1038/s41586-024-07403-2. PMC 11152992. PMID 38720072. Further elaboration to isoquinuclidine-containing tryptamines related to ibogaine led to a complete loss of 5-HT1A activity (Supplementary Table 1 and Extended Data Fig. 3). [...] Extended Data Fig. 3 | Global structure-activity landscape of tryptamine psychedelics at 5-HT1A and 5-HT2A receptors and their synthesis. [...] 5-MeO-DMT can be viewed as a deconstruction of ibogaine, a oneirogen with a complex polycyclic tryptamine structure (bottom of the circle). Iboga compounds show no activity at 5-HT1A and 5-HT2A receptors, but this activity re-emerges by deconstruction of the isoquinuclidine core to simple mono-cyclic tryptamines such as 5-MeOPipT (5-methoxypiperidinyl-tryptamine) and 4-F,5-MeO-PyrT (4-fluoro, 5-methoxypyrrolidinyl-tryptamine, right hemi-circle). [...] Supplementary Table 1: EC50 and Efficacy Summary of Tryptamine Analogs and Commercial Ligands [...]
  2. ^ Cameron LP, Tombari RJ, Lu J, Pell AJ, Hurley ZQ, Ehinger Y, et al. (January 2021). "A non-hallucinogenic psychedelic analogue with therapeutic potential". Nature. 589 (7842): 474–479. doi:10.1038/s41586-020-3008-z. PMC 7874389. PMID 33299186. Characteristic structural features of ibogaine include an indole, a 7-membered tetrahydroazepine and a bicyclic isoquinuclidine (Fig. 1). We reasoned that systematic deletion of these key structural elements would reveal the essential features of the psychoplastogenic pharmacophore of ibogaine. By adapting previously developed chemistry17, we were able to access a series of isoquinuclidine-containing compounds (8–11) that lacked the tetrahydroazepine and/or indole moieties that are characteristic of ibogaine (Extended Data Fig. 1a). Ibogalog 8a lacks both the indole and the tetrahydroazepine rings of ibogaine, whereas 9a–11a lack only the tetrahydroazepine. Ibogamine, ibogaine and noribogaine differ from 9a, 10a and 11a only by the presence of the C2–C16 bond (using the LeMen and Taylor conventions for atom numbering), respectively. [...] Except for 11a, ibogalogs containing the isoquinuclidine but lacking the tetrahydroazepine ring (8–10 and 11b) were either weak psychoplastogens or did not promote neuronal growth compared to the vehicle control (Extended Data Fig. 2).
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