Tabernanthalog
{{Chembox
| ImageFile = Tabernanthalog.svg
| ImageClass = skin-invert-image
| ImageFile1 = Tabernanthalog.png
| ImageSize = 200px
| ImageName1 = Ball and Stick 3D representation of a tabernanthalog molecule
| IUPACName = 8-methoxy-3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole
| Section1 = {{Chembox Identifiers
| ChemSpiderID = 114959868
| PubChem = 146026994
| StdInChI=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
| StdInChIKey = FNGNYGCPNKZYOG-UHFFFAOYSA-N
| SMILES = CN1CCC2=C(CC1)NC3=C2C=CC(=C3)OC
| CASNo = 2483829-59-8
}}
| Section2 = {{Chembox Properties
| C=14|H=18|N=2|O=1
}}
}}
Tabernanthalog (TBG, DLX-007){{cite journal | vauthors = Cameron LP, Tombari RJ, Lu J, Pell AJ, Hurley ZQ, Ehinger Y, Vargas MV, McCarroll MN, Taylor JC, Myers-Turnbull D, Liu T, Yaghoobi B, Laskowski LJ, Anderson EI, Zhang G, Viswanathan J, Brown BM, Tjia M, Dunlap LE, Rabow ZT, Fiehn O, Wulff H, McCorvy JD, Lein PJ, Kokel D, Ron D, Peters J, Zuo Y, Olson DE | display-authors = 6 | title = A non-hallucinogenic psychedelic analogue with therapeutic potential | journal = Nature | volume = 589 | issue = 7842 | pages = 474–479 | date = January 2021 | pmid = 33299186 | pmc = 7874389 | doi = 10.1038/s41586-020-3008-z | bibcode = 2021Natur.589..474C }} is a novel water-soluble, non-toxic azepinoindole{{cite journal | vauthors = Hester JB, Tang AH, Keasling HH, Veldkamp W | title = Azepinoindoles. I. Hexahydroazepino[4,5-b]indoles | journal = Journal of Medicinal Chemistry | volume = 11 | issue = 1 | pages = 101–106 | date = January 1968 | pmid = 5637151 | doi = 10.1021/jm00307a023 }} analog of the psychoactive drug Tabernanthine first synthesized by Professor David E. Olson at UC Davis.
Tabernanthalog is a non-hallucinogenic serotonin 5-HT2A receptor agonist.{{cite journal | vauthors = Cameron LP, Tombari RJ, Lu J, Pell AJ, Hurley ZQ, Ehinger Y, Vargas MV, McCarroll MN, Taylor JC, Myers-Turnbull D, Liu T, Yaghoobi B, Laskowski LJ, Anderson EI, Zhang G, Viswanathan J, Brown BM, Tjia M, Dunlap LE, Rabow ZT, Fiehn O, Wulff H, McCorvy JD, Lein PJ, Kokel D, Ron D, Peters J, Zuo Y, Olson DE | title = A non-hallucinogenic psychedelic analogue with therapeutic potential | journal = Nature | volume = 589 | issue = 7842 | pages = 474–479 | date = January 2021 | pmid = 33299186 | pmc = 7874389 | doi = 10.1038/s41586-020-3008-z | bibcode = 2021Natur.589..474C | url = }} It is also a serotonin 5-HT2B receptor antagonist. The drug is described as having high selectivity for the serotonin 5-HT2 receptors. Other targets of the drug include monoamine oxidase A (MAO-A), the α2A-adrenergic receptor, the serotonin 5-HT1B and 5-HT2C receptors, and the serotonin transporter (SERT).
In rodents, it was found to promote structural neural plasticity, reduce drug seeking behavior, and produce antidepressant like effects.{{cite journal | vauthors = Lu J, Tjia M, Mullen B, Cao B, Lukasiewicz K, Shah-Morales S, Weiser S, Cameron LP, Olson DE, Chen L, Zuo Y | display-authors = 6 | title = An analog of psychedelics restores functional neural circuits disrupted by unpredictable stress | journal = Molecular Psychiatry | volume = 26 | issue = 11 | pages = 6237–6252 | date = November 2021 | pmid = 34035476 | pmc = 8613316 | doi = 10.1038/s41380-021-01159-1 }}{{cite journal | vauthors = Peters J, Olson DE | title = Engineering Safer Psychedelics for Treating Addiction | journal = Neuroscience Insights | volume = 16 | pages = 26331055211033847 | date = 2021-07-20 | pmid = 34350400 | pmc = 8295933 | doi = 10.1177/26331055211033847 }} It has also been shown that it effectively reduces motivation for heroin and alcohol in rats. This indicates its efficacy in animals with a history of heroin and alcohol polydrug use.{{cite journal | vauthors = Heinsbroek JA, Giannotti G, Bonilla J, Olson DE, Peters J | title = Tabernanthalog Reduces Motivation for Heroin and Alcohol in a Polydrug Use Model | journal = Psychedelic Medicine | volume = 1 | issue = 2 | pages = 111–119 | date = June 2023 | pmid = 37360328 | doi = 10.1089/psymed.2023.0009 | pmc = 10286262 }}
Due to the rapidly-induced and enduring neuroplasticity, tabernanthalog is a member of the class of compounds known as non-hallucinogenic psychoplastogens. This compound, as well as related compounds, are licensed by Delix Therapeutics and are being developed as potential medicines for neuropsychiatric disorders.{{cite magazine | vauthors = Grace B | date = 6 March 2021 |title=Can we take the high out of psychedelics? |url=https://www.wired.co.uk/article/psychedelics-without-the-high |magazine=Wired |access-date=12 July 2022}}