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Tabernanthalog

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Tabernanthalog
Ball and Stick 3D representation of a tabernanthalog molecule
Names
IUPAC name
8-methoxy-3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole
Identifiers
3D model (JSmol)
ChemSpider
  • 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
  • CN1CCC2=C(CC1)NC3=C2C=CC(=C3)OC
Properties
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).

Tabernanthalog (TBG, DLX-007)[1] is a novel water-soluble, non-toxic azepinoindole[2] 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.[3] It is also a serotonin 5-HT2B receptor antagonist.[3] The drug is described as having high selectivity for the serotonin 5-HT2 receptors.[3] 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).[3]

In rodents, it was found to promote structural neural plasticity, reduce drug seeking behavior, and produce antidepressant like effects.[1][4][5][6] 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.[6]

Due to the rapidly-induced and enduring neuroplasticity, tabernanthalog is a member of the class of compounds known as non-hallucinogenic psychoplastogens.[1] This compound, as well as related compounds, are licensed by Delix Therapeutics and are being developed as potential medicines for neuropsychiatric disorders.[7]

See also

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References

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  1. ^ a b c 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. Bibcode:2021Natur.589..474C. doi:10.1038/s41586-020-3008-z. PMC 7874389. PMID 33299186.
  2. ^ Hester JB, Tang AH, Keasling HH, Veldkamp W (January 1968). "Azepinoindoles. I. Hexahydroazepino[4,5-b]indoles". Journal of Medicinal Chemistry. 11 (1): 101–106. doi:10.1021/jm00307a023. PMID 5637151.
  3. ^ a b c d 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 (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.
  4. ^ Lu J, Tjia M, Mullen B, Cao B, Lukasiewicz K, Shah-Morales S, et al. (November 2021). "An analog of psychedelics restores functional neural circuits disrupted by unpredictable stress". Molecular Psychiatry. 26 (11): 6237–6252. doi:10.1038/s41380-021-01159-1. PMC 8613316. PMID 34035476.
  5. ^ Peters J, Olson DE (2021-07-20). "Engineering Safer Psychedelics for Treating Addiction". Neuroscience Insights. 16: 26331055211033847. doi:10.1177/26331055211033847. PMC 8295933. PMID 34350400.
  6. ^ a b Heinsbroek JA, Giannotti G, Bonilla J, Olson DE, Peters J (June 2023). "Tabernanthalog Reduces Motivation for Heroin and Alcohol in a Polydrug Use Model". Psychedelic Medicine. 1 (2): 111–119. doi:10.1089/psymed.2023.0009. PMC 10286262. PMID 37360328.
  7. ^ Grace B (6 March 2021). "Can we take the high out of psychedelics?". Wired. Retrieved 12 July 2022.
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