Movatterモバイル変換


[0]ホーム

URL:


Jump to content
WikipediaThe Free Encyclopedia
Search

Tabernanthalog

From Wikipedia, the free encyclopedia

Pharmaceutical compound
Tabernanthalog
Clinical data
Other namesTBG; DLX-007; DLX007
Routes of
administration
Oral[1]
Drug classNon-selectiveserotonin receptor modulator; Non-hallucinogenicserotonin5-HT2A receptorpartial agonist
ATC code
  • None
Identifiers
  • 8-methoxy-3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole
CAS Number
PubChemCID
ChemSpider
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC14H18N2O
Molar mass230.311 g·mol−1
3D model (JSmol)
  • CN1CCC2=C(CC1)NC3=C2C=CC(=C3)OC
  • 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

Tabernanthalog (TBG; developmental code nameDLX-007) is anon-selectiveserotonin receptor modulator and putatively non-psychedelicpsychoplastogen of theibogalog group related to theiboga alkaloidtabernanthine but with a simplifiedchemical structure.[2][3] It was developed byDavid E. Olson and colleagues at theUniversity of California, Davis.[3] The drug is being developed byDelix Therapeutics as a potentialpharmaceutical drug for treatment ofneuropsychiatric disorders.[1][4]

Use and effects

[edit]

There have been informalanecdotal reports of the effects of tabernanthalog.[5][6][7] It is said to bepsychoactive and mildlyhallucinogenic at sufficiently high doses and to have a longduration.[6] Its hallucinogenic effects have been said to be similar to but weaker than those ofserotonergic psychedelics.[6][7] There were also reports ofside effects likenausea,dizziness,stomach discomfort, anddiarrhea.[6][7] However, it is unclear whether the reports have always employed actual tabernanthalog.[6]

Interactions

[edit]
See also:Psychedelic drug § Interactions, andTrip killer § Serotonergic psychedelic antidotes

Pharmacology

[edit]

Pharmacodynamics

[edit]
Tabernanthalog activities
TargetAffinity (Ki, nM)
5-HT1A39%BI @ 10 μM
14,600 (
EC50Tooltip half-maximal effective concentration)
95% (EmaxTooltip maximal efficacy)
5-HT1B66%BI @ 10 μM
34 (
EC50)
87% (
Emax)
5-HT1DND (Ki)
2,180 (
EC50)
76% (
Emax)
5-HT1END (Ki)
2,784 (
EC50)
117% (
Emax)
5-HT1FND (Ki)
40 (
EC50)
64% (
Emax)
5-HT2A4,440 (Ki)
57%BI @ 10 μM
147–4,570 (
EC50)
8–91% (
Emax)
5-HT2B439 (Ki)
86%BI @ 10 μM
2,827 or
IA (EC50)
46% or
IA (Emax)
5-HT2C28,590 (Ki)
99%BI @ 10 μM
13–69 (
EC50)
21–99% (
Emax)
5-HT314%BI @ 10 μM
5-HT4ND (Ki)
>10,000 (
EC50)
5-HT5AND (Ki)
>10,000 (
EC50)
5-HT6ND (Ki)
132–214 (
EC50)
88–133% (
Emax)
5-HT7ND (Ki)
>10,000 (
EC50)
α1Aα1D15–20%BI @ 10 μM
α2A81%BI @ 10 μM
α2B27%BI @ 10 μM
α2CND
β1β29%BI @ 10 μM
D1,D23–18%BI @ 10 μM
D3D5ND
H135%BI @ 10 μM
H2–12%BI @ 10 μM
H3,H4ND
M1M42–18%BI @ 10 μM
M5ND
nAChTooltip Nicotinic acetylcholine receptor16–19%BI @ 10 μM
I1,I2ND
σ1,σ2ND
MORTooltip μ-Opioid receptor17%BI @ 10 μM
IA (EC50)
DORTooltip δ-Opioid receptor14%BI @ 10 μM
IA (EC50)
KORTooltip κ-Opioid receptor7%BI @ 10 μM
>10,000 (
EC50)
NMDARTooltip N-Methyl-D-aspartate receptor0–3%BI @ 10 μM (rat)
TAAR1Tooltip Trace amine-associated receptor 1ND
SERTTooltip Serotonin transporter88%BI @ 10 μM
600 (
IC50Tooltip half-maximal inhibitory concentration)
NETTooltip Norepinephrine transporterND (Ki)
5,400 (
IC50)
DATTooltip Dopamine transporterND (Ki)
65,000 (
IC50)
VMATTooltip Vesicular monoamine transporter10%BI @ 10 μM
MAO-ATooltip Monoamine oxidase A66%BI @ 10 μM
15,100 (
IC50)
MAO-BTooltip Monoamine oxidase B16%BI @ 10 μM
28%
FI @ 100 μM
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified.Refs:[3][8][2][9][10][11]

Tabernanthalog is anon-selective and non-psychedelicserotonin receptor modulator, including acting as anagonist of theserotonin5-HT1B,5-HT1F,5-HT2A,5-HT2C, and5-HT6 receptors and as an agonist orantagonist of theserotonin5-HT2B receptor.[3][8][10] It also shows significant binding to theserotonin transporter (SERT) (acting as aserotonin reuptake inhibitor), theα2A-adrenergic receptor, andmonoamine oxidase A (MAO-A).[3] In contrast toiboga alkaloids likeibogaine andnoribogaine, tabernanthalog showed negligible interactions withopioid receptors, theNMDA receptor, and certainnicotinic acetylcholine receptors.[3] However, in subsequent research, it weakly inhibited certain nicotinic acetylcholine receptors, as well as, to a much lesser extent, theGABAA receptor.[12] Tabernanthalog was found to be 100-fold lesspotent at thehERGantitarget compared to ibogaine, and hence is thought to have a much lower potential forcardiotoxicity.[3]

Tabernanthalog did not produce thehead-twitch response, a behavioral proxy ofpsychedelic effects, in rodents, and hence appears to be non-hallucinogenic.[3] However, it was found to promote structuralneuroplasticity (i.e., to act as apsychoplastogen), reducedrug-seeking behavior, and produceantidepressant-like effects.[3][13][14][15] It has also been shown that it reduces motivation for heroin andalcohol in rodents.[15]

History

[edit]

Tabernanthalog was first described in thescientific literature byDavid E. Olson and colleagues at theUniversity of California, Davis in January 2021.[3][16]

Society and culture

[edit]

Grey market use

[edit]

Tabernanthalog has been known to be sold online byresearch chemical vendors for purposes such as "nootropic" use.[6]

Research

[edit]

Tabernanthalog is under development for the treatment ofcentral nervous system disorders (CNS disorders).[1][17] It is being developed byDelix Therapeutics.[1][17] As of May 2025, no recent development has been reported.[1] It had reached thepreclinical research stage of development.[1][17] Aphase 1clinical trial was being planned for the first half of 2023.[1] Delix Therapeutics also partnered withNational Institute on Drug Abuse (NIDA) to evaluate tabernanthalog for the treatment ofsubstance-related disorders in December 2021.[1]

See also

[edit]

References

[edit]
  1. ^abcdefgh"DLX 7".AdisInsight. 28 May 2025. Retrieved31 July 2025.
  2. ^abSharp T, Ippolito A (May 2025)."Neuropsychopharmacology of hallucinogenic and non-hallucinogenic 5-HT2A receptor agonists".Br J Pharmacol bph.70050.doi:10.1111/bph.70050.PMID 40405723.
  3. ^abcdefghijCameron 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.
  4. ^Grace B (6 March 2021)."Can we take the high out of psychedelics?".Wired. Retrieved12 July 2022.
  5. ^Love, Shayla (20 October 2024)."Tripping on Nothing".The Atlantic. Archived fromthe original on 8 February 2025.
  6. ^abcdefHardman, Josh (19 July 2023)."Non-Hallucinogenic Trip Reports: Searching for the Tabernanthalog Tasters".Psychedelic Alpha. Retrieved14 October 2025.
  7. ^abcJuliani, Arthur (30 December 2023)."A Phenomenological Report on the Novel Non-Hallucinogenic Psychedelic Tabernanthalog".Medium. Retrieved14 October 2025.
  8. ^abArias HR, Micheli L, Rudin D, Bento O, Borsdorf S, Ciampi C, Marin P, Ponimaskin E, Manetti D, Romanelli MN, Ghelardini C, Liechti ME, Di Cesare Mannelli L (August 2024). "Non-hallucinogenic compounds derived from iboga alkaloids alleviate neuropathic and visceral pain in mice through a mechanism involving 5-HT2A receptor activation".Biomed Pharmacother.177 116867.doi:10.1016/j.biopha.2024.116867.hdl:2158/1371514.PMID 38889634.
  9. ^Ippolito A, Vasudevan S, Hurley S, Gilmour G, Westhorpe F, Churchill G, Sharp T (June 2025)."Evidence that 5-HT2A receptor signalling efficacy and not biased agonism differentiates serotonergic psychedelic from non-psychedelic drugs".Br J Pharmacol bph.70109.doi:10.1111/bph.70109.PMID 40545270.
  10. ^abArias HR, Rudin D, Luethi D, Valenta J, Leśniak A, Czartoryska Z, Olejarz-Maciej A, Doroz-Płonka A, Manetti D, De Deurwaerdère P, Romanelli MN, Handzlik J, Liechti ME, Chagraoui A (January 2025)."The psychoplastogens ibogaminalog and ibogainalog induce antidepressant-like activity in naïve and depressed mice by mechanisms involving 5-HT2A receptor activation and serotonergic transmission".Prog Neuropsychopharmacol Biol Psychiatry.136 111217.doi:10.1016/j.pnpbp.2024.111217.PMID 39662723.
  11. ^Arias HR, Micheli L, Jensen AA, Galant S, Vandermoere F, Venturi D, Manetti D, Romanelli MN, Ghelardini C, Marin P, Di Cesare Mannelli L (March 2025). "Ibogalogs decrease neuropathic pain in mice through a mechanism involving crosstalk between 5-HT2A and mGlu2 receptors".Biomed Pharmacother.184 117887.doi:10.1016/j.biopha.2025.117887.hdl:2158/1423286.PMID 39938347.
  12. ^Tae HS, Ortells MO, Yousuf A, Xu SQ, Akk G, Adams DJ, Arias HR (May 2024)."Tabernanthalog and ibogainalog inhibit the α7 and α9α10 nicotinic acetylcholine receptors via different mechanisms and with higher potency than the GABAA receptor and CaV2.2 channel".Biochem Pharmacol.223 116183.doi:10.1016/j.bcp.2024.116183.PMC 11151864.PMID 38580167.
  13. ^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.
  14. ^Peters J, Olson DE (20 July 2021)."Engineering Safer Psychedelics for Treating Addiction".Neuroscience Insights.16 26331055211033847.doi:10.1177/26331055211033847.PMC 8295933.PMID 34350400.
  15. ^abHeinsbroek 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.
  16. ^Jaster, Alaina M. (13 January 2021)."Researchers Synthesize Novel Compound, Tabernanthalog, a Non-Hallucinogenic Ibogaine Analog".Psychedelic Science Review. Retrieved14 October 2025.
  17. ^abc"Delving into the Latest Updates on DLX-7 with Synapse".Synapse. 7 August 2025. Retrieved14 October 2025.

External links

[edit]
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT37
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
α1
Agonists
Antagonists
α2
Agonists
Antagonists
β
Agonists
Antagonists
nAChRsTooltip Nicotinic acetylcholine receptors
Agonists
(andPAMsTooltip positive allosteric modulators)
Antagonists
(andNAMsTooltip negative allosteric modulators)
Precursors
(andprodrugs)
DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)
NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)
SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)
VMATsTooltip Vesicular monoamine transporters
Others
Tryptamines
4-Hydroxytryptamines
andesters/ethers
5-Hydroxy- and
5-methoxytryptamines
N-Acetyltryptamines
α-Alkyltryptamines
Cyclized tryptamines
Isotryptamines
Related compounds
Retrieved from "https://en.wikipedia.org/w/index.php?title=Tabernanthalog&oldid=1322835974"
Categories:
Hidden categories:

[8]ページ先頭

©2009-2025 Movatter.jp