Chemistry:6-Hydroxytryptamine

From HandWiki

6-Hydroxytryptamine (6-HT or 6-HO-T) is a serotonin receptor modulator of the tryptamine family related to serotonin.[1][2][3] It is a positional isomer of serotonin (5-hydroxytryptamine; 5-HT) and of 4-hydroxytryptamine (4-HT).[1][2][3]

Pharmacology

6-Hydroxytryptamine shows dramatically reduced affinity for serotonin receptors, including the serotonin 5-HT1A, 5-HT1B, 5-HT2A, and 5-HT2C receptors (Ki = 1,590 nM, 5,890 nM, 11,500 nM, and 5,500 nM, respectively), compared to serotonin, 4-hydroxytryptamine, 5-methoxytryptamine, and certain other tryptamines.[3] It did not produce hyperlocomotion in rodents but did partially reverse reserpine-induced hypoactivity.[4] 6-Hydroxytryptamine appears to be less susceptible to metabolism by monoamine oxidase (MAO) than serotonin.[5]

History

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

Derivatives

Certain β-carbolines and harmala alkaloids, such as harmol, harmalol, and tetrahydroharmol, as well as their O-methyl (methoxy) analogues including harmine, harmaline, and tetrahydroharmine, are notable in being naturally occurring cyclized tryptamine derivatives of 6-hydroxytryptamine.[7][8] The same is true of certain iboga alkaloids, such as tabernanthine and ibogaline.[9][10][11][12] 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.[13][14]

See also

References

  1. ↑ 1.0 1.1 "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. 1975. pp. 98–144. ISBN 978-0-85608-011-1. OCLC 2176880. https://bitnest.netfirms.com/external/Books/978-0-85608-011-1. 
  2. ↑ 2.0 2.1 "Indole Hallucinogens Derived from Tryptophan". The Hallucinogens. Elsevier. 1967. pp. 443–516 (468). doi:10.1016/b978-1-4832-3296-6.50008-2. ISBN 978-1-4832-3296-6. OCLC 332437. https://bitnest.netfirms.com/external/Books/TheHallucinogens#page=451. 
  3. ↑ 3.0 3.1 3.2 "Central serotonin receptors as targets for drug research". Journal of Medicinal Chemistry 30 (1): 1–12. January 1987. doi:10.1021/jm00384a001. PMID 3543362. "Some selected binding data are shown in Table III. N-Monomethylation and N,N-dimethylation of 5-HT decrease its affinity for 5-HT1 binding sites. Relocation of the hydroxyl group to the 4- or 6-position (ie., 4-hydroxytryptamine and 6-hydroxytryptamine, respectively) also decreases affinity (except that the affinity of 4-hydroxytryptamine is not very different from that of 5-HT for 5-HT1c sites).". 
  4. ↑ "Synthesis and pharmacological activity of alkylated tryptamines". Journal of Medicinal Chemistry 9 (3): 341–344. May 1966. doi:10.1021/jm00321a017. PMID 5960901. https://chemistry.mdma.ch/hiveboard/picproxie_docs/000512604-Synthesis_and_Pharmacological_Activity_of_Alkylate.pdf. 
  5. ↑ "A note on the oxidative deamination of isomers of 5-hydroxytryptamine and other indolealkylamines". The Journal of Pharmacy and Pharmacology 12: 761–764. December 1960. doi:10.1111/j.2042-7158.1960.tb12743.x. PMID 13697284. 
  6. ↑ "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. 
  7. ↑ 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. 
  8. ↑ "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. 
  9. ↑ "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. 
  10. ↑ "The Iboga Alkaloids". Progress in the Chemistry of Organic Natural Products 105: 89–136. 2017. doi:10.1007/978-3-319-49712-9_2. ISBN 978-3-319-49711-2. PMID 28194562. http://www.puzzlepiece.org/ibogaine/literature/lavaud2017.pdf. 
  11. ↑ "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. 
  12. ↑ "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. 
  13. ↑ "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. 




Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:6-Hydroxytryptamine&oldid=4175641"