Tabernanthalog

Tabernanthalog
Names
	IUPAC name 8-methoxy-3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indol
Identifiers
3D model (JSmol)	Interactive image;
PubChem CID	146026994;
CompTox Dashboard (EPA)	DTXSID301336754 ;
	InChI InChI=1S/C14H18N2O/c1-16-7-5-12-11-4-3-10(17-2)9-14(11)15-13(12)6-8-16/h3-4,9,15H,5-8H2,1-2H3 Key: FNGNYGCPNKZYOG-UHFFFAOYSA-N;
	SMILES CN1CCC2=C(CC1)NC3=C2C=CC(=C3)OC;
Properties
Chemical formula	C14H18N2O
Molar mass	230.311 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Tabernanthalog is a novel water-soluble, non-toxic azepinoindole^[1] analog of the psychoactive drug ibogaine first synthesized by Professor David E. Olson at UC Davis.^[2]

In rodents, it was found to promote structural neural plasticity, reduce drug seeking behavior, and produce antidepressant like effects.^[2]^[3] Due to the rapidly-induced and enduring neuroplasticity, Tabernanthalog is a member of the class of compounds known as non-hallucinogenic psychoplastogens.^[2] This compound, as well as related compounds, are licensed by Delix Therapeutics and are being developed as potential medicines for neuropsychiatric disorders.^[4]

References

^ Hester, J B; Tang, A H.; Keasling, H H.; Veldkamp, W (17 Dec 1968). "Azepinoindoles. I. Hexahydroazepino[4,5-b]indoles". J Med Chem. 11 (1): 101–106. doi:10.1021/jm00307a023.
^ ^a ^b ^c
Cameron, Lindsay P.; Tombari, Robert J.; Lu, Ju; Pell, Alexander J.; Hurley, Zefan Q.; Ehinger, Yann; Vargas, Maxemiliano V.; McCarroll, Matthew N.; Taylor, Jack C.; Myers-Turnbull, Douglas; Liu, Taohui (9 Dec 2020). "A non-hallucinogenic psychedelic analogue with therapeutic potential". Nature. 589 (7842): 474–479. doi:10.1038/s41586-020-3008-z. ISSN 1476-4687. PMC 7874389. PMID 33299186.
- Andy Fell (December 9, 2020). "New Compound Related to Psychedelic Ibogaine Could Treat Addiction, Depression".
^ Peters, Jamie; Olson, David E (2021-07-20). "Engineering Safer Psychedelics for Treating Addiction". Neuroscience Insights. 16: 263310552110338. doi:10.1177/26331055211033847. ISSN 2633-1055. PMC 8295933. PMID 34350400.
^ Grace, Brown. "Can we take the high out of psychedelics?". Wired. Retrieved 12 July 2022.

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[1] Hester, J B; Tang, A H.; Keasling, H H.; Veldkamp, W (17 Dec 1968). "Azepinoindoles. I. Hexahydroazepino[4,5-b]indoles". J Med Chem. 11 (1): 101–106. doi:10.1021/jm00307a023.

[pmid33299186-2] Cameron, Lindsay P.; Tombari, Robert J.; Lu, Ju; Pell, Alexander J.; Hurley, Zefan Q.; Ehinger, Yann; Vargas, Maxemiliano V.; McCarroll, Matthew N.; Taylor, Jack C.; Myers-Turnbull, Douglas; Liu, Taohui (9 Dec 2020). "A non-hallucinogenic psychedelic analogue with therapeutic potential". Nature. 589 (7842): 474–479. doi:10.1038/s41586-020-3008-z. ISSN 1476-4687. PMC 7874389. PMID 33299186.
Andy Fell (December 9, 2020). "New Compound Related to Psychedelic Ibogaine Could Treat Addiction, Depression".

[3] Andy Fell (December 9, 2020). "New Compound Related to Psychedelic Ibogaine Could Treat Addiction, Depression".

[3] Peters, Jamie; Olson, David E (2021-07-20). "Engineering Safer Psychedelics for Treating Addiction". Neuroscience Insights. 16: 263310552110338. doi:10.1177/26331055211033847. ISSN 2633-1055. PMC 8295933. PMID 34350400.

[4] Grace, Brown. "Can we take the high out of psychedelics?". Wired. Retrieved 12 July 2022.

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[2]

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[4]

See also

References