Tabernanthalog

Last updated
Tabernanthalog
Tabernanthalog.svg
Tabernanthalog.png
Names
IUPAC name
8-methoxy-3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • 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) [1] is a novel water-soluble, non-toxic azepinoindole [2] analog of the psychoactive drug ibogaine first synthesized by Professor David E. Olson at UC Davis.

In rodents, it was found to promote structural neural plasticity, reduce drug seeking behavior, and produce antidepressant like effects. [1] [3] [4] [5] 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

Related Research Articles

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<span class="mw-page-title-main">Psychedelic drug</span> Hallucinogenic class of psychoactive drug

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<span class="mw-page-title-main">Ibogaine</span> Psychoactive substance found in plants in the family Apocynaceae

Ibogaine is an psychoactive indole alkaloid obtained either by extraction from plants in the family Apocynaceae such as Tabernanthe iboga, Voacanga africana, and Tabernaemontana undulata or by semi-synthesis from the precursor compound voacangine, another plant alkaloid. The total synthesis of ibogaine was described in 1956. Structural elucidation by X-ray crystallography was completed in 1960.

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<span class="mw-page-title-main">AAZ-A-154</span> Chemical compound

AAZ-A-154 is a novel isotryptamine derivative which acts as a 5-HT2A receptor agonist discovered and synthesized by the lab of Professor David E. Olson at UCDavis. Animal studies suggest that it produces antidepressant effects without the psychedelic action typical of drugs from this class. In tests, AAZ-A-154 had antidepressant effects in mice without causing the head-twitch response linked to hallucinogenic effects. Due to the rapidly-induced and enduring neuroplasticity, AAZ-A-154 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.

Psychoplastogens are a group of small molecule drugs that produce rapid and sustained effects on neuronal structure and function, intended to manifest therapeutic benefit after a single administration. Several existing psychoplastogens have been identified and their therapeutic effects demonstrated; several are presently at various stages of development as medications including ketamine, MDMA, scopolamine, and the serotonergic psychedelics, including LSD, psilocin, DMT, and 5-MeO-DMT. Compounds of this sort are being explored as therapeutics for a variety of brain disorders including depression, addiction, and PTSD. The ability to rapidly promote neuronal changes via mechanisms of neuroplasticity was recently discovered as the common therapeutic activity and mechanism of action.

David E. Olson is an American chemist and neuroscientist. He is an associate professor of chemistry, biochemistry and molecular medicine at the University of California, Davis, and is the founding director of the UC Davis Institute for Psychedelics and Neurotherapeutics.

Delix Therapeutics is an American biotech company based in Boston, Massachusetts. The company develops novel neuroplasticity-promoting therapeutics for central nervous system (CNS) diseases such as depression and post-traumatic stress disorder (PTSD). It was co-founded in 2019 by David E. Olson and Nick Haft.

<span class="mw-page-title-main">DM-506</span> Chemical compound

DM-506 (Ibogaminalog) is a drug first invented in the 1960s, which acts as both a partial agonist at the 5-HT2A receptor, and a negative allosteric modulator at the α7 and α9α10 nicotinic acetylcholine receptors. It can be regarded as a structurally simplified derivative of ibogaine and has been researched both for anti-addictive effects and for the treatment of neuropathic pain.

References

  1. 1 2 3 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. 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.
  4. 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.
  5. 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.
  6. 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.