Chemistry:6-Methoxytryptamine

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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]

Pharmacology

6-Methoxytryptamine is a potent serotonin–norepinephrine–dopamine releasing agent (SNDRA), with EC50 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 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. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 "Alpha-ethyltryptamines as dual dopamine-serotonin releasers". Bioorganic & Medicinal Chemistry Letters 24 (19): 4754–4758. October 2014. doi:10.1016/j.bmcl.2014.07.062. PMID 25193229. 
  2. ↑ "The relative activities of some tryptamine analogues on the isolated rat stomach strip preparation". British Journal of Pharmacology and Chemotherapy 14 (1): 87–98. March 1959. doi:10.1111/j.1476-5381.1959.tb00933.x. PMID 13651584. 
  3. ↑ Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. http://www.erowid.org/library/books_online/tihkal/tihkal.shtml. 
  4. ↑ "Investigation of hallucinogenic and related beta-carbolines". Drug and Alcohol Dependence 50 (2): 99–107. April 1998. doi:10.1016/s0376-8716(97)00163-4. PMID 9649961. 
  5. ↑ "Pharmacology of Ibogaine and Ibogaine-Related Alkaloids". The Alkaloids: Chemistry and Biology. 52. Elsevier. 1999. pp. 197–231. doi:10.1016/s0099-9598(08)60027-9. ISBN 978-0-12-469552-8. https://linkinghub.elsevier.com/retrieve/pii/S0099959808600279. Retrieved 17 June 2025. 
  6. ↑ "The Iboga Alkaloids". Progress in the Chemistry of Organic Natural Products. 105. 2017. pp. 89–136. doi:10.1007/978-3-319-49712-9_2. ISBN 978-3-319-49711-2. http://www.puzzlepiece.org/ibogaine/literature/lavaud2017.pdf. 
  7. ↑ "The iboga enigma: the chemistry and neuropharmacology of iboga alkaloids and related analogs". Natural Product Reports 38 (2): 307–329. March 2021. doi:10.1039/d0np00033g. PMID 32794540. 
  8. ↑ "Non-hallucinogenic psychedelics for mood and anxiety disorders: A systematic review". Psychiatry Research 349. July 2025. doi:10.1016/j.psychres.2025.116532. PMID 40354769. 
  9. ↑ "A non-hallucinogenic psychedelic analogue with therapeutic potential". Nature 589 (7842): 474–479. January 2021. doi:10.1038/s41586-020-3008-z. PMID 33299186. Bibcode: 2021Natur.589..474C. 




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