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Zalsupindole

From Wikipedia, the free encyclopedia
Chemical compound

Not to be confused withDLX1.
Pharmaceutical compound
Zalsupindole
Clinical data
Other namesDLX-001; DLX-1; DLX001; DLX1; AAZ-A-154; AAZ; (R)-5-Methoxy-N,N-dimethyl-α-methylisotryptamine; (R)-5-MeO-α-methyl-isoDMT; (R)-5-MeO-N,N-dimethyl-isoAMT
Drug classNon-hallucinogenicserotonin5-HT2A receptoragonist;Psychoplastogen
Identifiers
  • (2R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine
CAS Number
PubChemCID
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC14H20N2O
Molar mass232.327 g·mol−1
3D model (JSmol)
  • CN(C)[C@H](C)Cn1ccc2cc(ccc21)OC
  • InChI=1S/C14H20N2O/c1-11(15(2)3)10-16-8-7-12-9-13(17-4)5-6-14(12)16/h5-9,11H,10H2,1-4H3/t11-/m1/s1
  • Key:KHEUWLQKCXGVEL-LLVKDONJSA-N

Zalsupindole,[1] also known by its developmental code namesDLX-001 andAAZ-A-154 and as(R)-5-methoxy-N,N-dimethyl-α-methylisotryptamine, is a novelisotryptaminederivative that acts as aserotonin5-HT2A receptoragonist and was discovered andsynthesized by the lab of ProfessorDavid E. Olson at theUniversity of California, Davis.[2][3][4][5] It is being developed for the treatment ofmajor depressive disorder and othercentral nervous system disorders.[2][3]

Animal studies suggest that it producesantidepressant-like effects without thepsychedelic-like effects typical of drugs from this class.[6][7][4][5] In tests, zalsupindole had antidepressant-like effects in mice without causing thehead-twitch response linked tohallucinogenic effects.[8][4][5] Due to the rapidly-induced and enduringneuroplasticity, zalsupindole is a member of the class of compounds known as non-hallucinogenicpsychoplastogens.[9][4][5] Aphase 1dose-rangingclinical trial confirmed that zalsupindole is non-hallucinogenic in humans across a dose range of 2 to 360 mg.[10]

The drug has been reported to beselective for the serotonin5-HT2 receptors.[11] It is anantagonist of the serotonin5-HT2B receptor and showed nocardiovascularsafety signals in animals.[5] Zalsupindole isorallybioavailable andcentrallypenetrant in animals.[5]

Zalsupindole is a member of the isotryptamine group of compounds.[12][13] It is a combined derivative ofisoDMT,5-MeO-isoDMT, andisoAMT.[12][13] Another related compound is6-MeO-isoDMT.[12] Zalsupindole is a close isotryptamineanalogue ofα,N,N,O-tetramethylserotonin (α,N,N,O-TMS).[13]

Zalsupindole, as well as related compounds, are licensed byDelix Therapeutics and are being developed as potential medicines forneuropsychiatric disorders.[9][2][3] As of December 2023, zalsupindole is inphase 1clinical trials for major depressive disorder and other central disorders.[2][3]

See also

[edit]

References

[edit]
  1. ^https://iris.who.int/bitstream/handle/10665/380497/9789240107038-eng.pdf "zalsupindolum zalsupindole (2R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine antidepressant"
  2. ^abcd"DLX 1".AdisInsight. 11 December 2023. Retrieved2 November 2024.
  3. ^abcd"Delving into the Latest Updates on DLX-001 with Synapse".Synapse. 1 November 2024. Retrieved2 November 2024.
  4. ^abcdRasmussen K, Chytil M, Agrawal R, Leach P, Gillie D, Mungenast A, et al. (2024). "14. Preclinical Pharmacology of DLX-001, a Novel Non-Hallucinogenic Neuroplastogen With the Potential for Treating Neuropsychiatric Diseases".Biological Psychiatry.95 (10). Elsevier BV: S80.doi:10.1016/j.biopsych.2024.02.192.ISSN 0006-3223.
  5. ^abcdefRasmussen K, Engel S, Chytil M, Koenig A, Meyer R, Rus M, et al. (December 2023)."ACNP 62nd Annual Meeting: Poster Abstracts P251 - P500: P361. Preclinical Pharmacology of DLX-001, a Novel Non-Hallucinogenic Neuroplastogen With the Potential for Treating Neuropsychiatric Diseases".Neuropsychopharmacology.48 (Suppl 1): 211–354 (274–275).doi:10.1038/s41386-023-01756-4.PMC 10729596.PMID 38040810.
  6. ^Dong C, Ly C, Dunlap LE, Vargas MV, Sun J, Hwang IW, et al. (May 2021)."Psychedelic-inspired drug discovery using an engineered biosensor".Cell.184 (10): 2779–2792.e18.doi:10.1016/j.cell.2021.03.043.PMC 8122087.PMID 33915107.
  7. ^WO 2020176597, Olson DE, Dunlap L, Wagner FF, "N-substituted indoles and other heterocycles for treating brain disorders", published 3 September 2020, assigned to The Regents of the University of California 
  8. ^Cross R (2021-09-27)."Delix raises $70 million to synthesize psychedelic-inspired drugs".cen.acs.org.Archived from the original on 2021-09-27. Retrieved2022-01-14.
  9. ^ab"Can we take the high out of psychedelics?".Wired UK.ISSN 1357-0978. Retrieved2022-07-07.
  10. ^Koenig A, van der Aa L, Pelletier N, Patat A, Viardot G, Olson D, et al. (2024)."ACNP 63rd Annual Meeting: Poster Abstracts P1-P304: P163. Phase I Results for DLX-001, a Novel Neuroplastogen Under Development for the Treatment of Major Depressive Disorder"(PDF).Neuropsychopharmacology.49 (S1): 65–235 (157–158).doi:10.1038/s41386-024-02011-0.ISSN 0893-133X.PMC 11627186.PMID 39643633. Retrieved31 January 2025.
  11. ^Dunlap LE (2022).Development of Non-Hallucinogenic Psychoplastogens (Thesis). University of California, Davis. Retrieved18 November 2024.
  12. ^abcDuan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants".Chem Rev.124 (1):124–163.doi:10.1021/acs.chemrev.3c00375.PMID 38033123.
  13. ^abc"(2R)-1-(5-Methoxyindol-1-yl)-N,N-dimethylpropan-2-amine".PubChem. Retrieved27 November 2024.


5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
Tryptamines
N-Acetyltryptamines
α-Alkyltryptamines
Triptans
Cyclized tryptamines
Isotryptamines
Related compounds
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