6-Methoxytryptamine

Last updated

6-Methoxytryptamine
6-Methoxytryptamine.svg
Clinical data
Other names6-Methoxy-T; 6-MeO-T; PAL-263; PAL263
Drug class Monoamine releasing agent; Serotonin–norepinephrine–dopamine releasing agent; Serotonin receptor modulator
ATC code
  • None
Identifiers
  • 2-(6-methoxy-1H-indol-3-yl)ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.020.708 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C11H14N2O
Molar mass 190.246 g·mol−1
3D model (JSmol)
  • COC1=CC2=C(C=C1)C(=CN2)CCN
  • InChI=1S/C11H14N2O/c1-14-9-2-3-10-8(4-5-12)7-13-11(10)6-9/h2-3,6-7,13H,4-5,12H2,1H3
  • Key:VOCGEKMEZOPDFP-UHFFFAOYSA-N

6-Methoxytryptamine (6-MeO-T; developmental code name PAL-263) is a monoamine releasing agent and serotonin receptor modulator of the tryptamine family. [1] It is a positional isomer of 5-methoxytryptamine. [1]

Contents

Pharmacology

6-Methoxytryptamine is a potent serotonin–norepinephrine–dopamine releasing agent (SNDRA), with EC50 Tooltip half-maximal effective concentration values for monoamine release induction of 53.8 nM for serotonin, 113 nM for dopamine, and 465 nM for norepinephrine in rat brain synaptosomes. [1] It is also a full agonist of the serotonin 5-HT2A receptor, but with very low potency; its EC50 and Emax Tooltip maximal efficacy at this receptor were 2,443 nM and 111%, respectively. [1] In a series of tryptamine derivatives, 6-methoxytryptamine was the least potent serotonin 5-HT2A receptor agonist, while 5-methoxytryptamine was the most potent serotonin 5-HT2A receptor agonist, with 5-methoxytryptamine showing approximately 4,857-fold higher potency in terms of serotonin 5-HT2A receptor agonism than 6-methoxytryptamine. [1] Conversely, whereas 6-methoxytryptamine was a potent monoamine releasing agent, 5-methoxytryptamine showed very low potency in this regard. [1]

History

6-Methoxytryptamine was first described in the scientific literature by the 1950s. [2]

Derivatives

Certain β-carbolines and harmala alkaloids, such as harmine, harmaline, and tetrahydroharmine, are notable in being naturally occurring cyclized tryptamine derivatives of 6-methoxytryptamine. [3] [4] The same is true of certain iboga alkaloids, such as tabernanthine and ibogaline. [5] [6] [7] [8] Tabernanthalog (DLX-007) is a synthetic simplified ibogalog analogue of tabernanthine that is under development for use as a potential pharmaceutical drug in the treatment of neuropsychiatric disorders. [9] [10]

See also

References

  1. 1 2 3 4 5 6 Blough BE, Landavazo A, Partilla JS, Decker AM, Page KM, Baumann MH, et al. (October 2014). "Alpha-ethyltryptamines as dual dopamine-serotonin releasers". Bioorganic & Medicinal Chemistry Letters. 24 (19): 4754–4758. doi:10.1016/j.bmcl.2014.07.062. PMC   4211607 . PMID   25193229.
  2. ↑ Vane JR (March 1959). "The relative activities of some tryptamine analogues on the isolated rat stomach strip preparation". British Journal of Pharmacology and Chemotherapy. 14 (1): 87–98. doi:10.1111/j.1476-5381.1959.tb00933.x. PMC   1481817 . PMID   13651584.
  3. ↑ Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252.
  4. ↑ Grella B, Dukat M, Young R, Teitler M, Herrick-Davis K, Gauthier CB, et al. (April 1998). "Investigation of hallucinogenic and related beta-carbolines". Drug and Alcohol Dependence. 50 (2): 99–107. doi:10.1016/s0376-8716(97)00163-4. PMID   9649961.
  5. ↑ Skolnick P, Popik P (1999). "Pharmacology of Ibogaine and Ibogaine-Related Alkaloids". The Alkaloids: Chemistry and Biology. Vol. 52. Elsevier. pp. 197–231. doi:10.1016/s0099-9598(08)60027-9. ISBN   978-0-12-469552-8 . Retrieved 17 June 2025.
  6. ↑ Lavaud C, Massiot G (2017). "The Iboga Alkaloids" (PDF). Progress in the Chemistry of Organic Natural Products. Vol. 105. pp. 89–136. doi:10.1007/978-3-319-49712-9_2. ISBN   978-3-319-49711-2. PMID   28194562.
  7. ↑ Iyer RN, Favela D, Zhang G, Olson DE (March 2021). "The iboga enigma: the chemistry and neuropharmacology of iboga alkaloids and related analogs". Natural Product Reports. 38 (2): 307–329. doi:10.1039/d0np00033g. PMC   7882011 . PMID   32794540.
  8. ↑ Chen MJ, Chen-Li D, Chisamore N, Husain MI, Di Vincenzo JD, Mansur RB, et al. (July 2025). "Non-hallucinogenic psychedelics for mood and anxiety disorders: A systematic review". Psychiatry Research. 349 116532. doi: 10.1016/j.psychres.2025.116532 . PMID   40354769.
  9. ↑ 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.


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