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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. ^ a b Brimblecombe RW, Pinder RM (1975). “Indolealkylamines and Related Compounds”. Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144. ISBN 978-0-85608-011-1. OCLC 2176880. OL 4850660M.
  2. ^ a b Hoffer A, Osmond H (1967). “Indole Hallucinogens Derived from Tryptophan”. The Hallucinogens. Elsevier. pp. 443–516 (468). doi:10.1016/b978-1-4832-3296-6.50008-2. ISBN 978-1-4832-3296-6. LCCN 66030086. OCLC 332437. OL 35255701M.
  3. ^ a b c Glennon RA (January 1987). “Central serotonin receptors as targets for drug research”. Journal of Medicinal Chemistry. 30 (1): 1–12. 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. ^ Kalir A, Szara S (May 1966). “Synthesis and pharmacological activity of alkylated tryptamines” (PDF). Journal of Medicinal Chemistry. 9 (3): 341–344. doi:10.1021/jm00321a017. PMID 5960901.
  5. ^ Erspamer V, Ferrini R, Glasser A (December 1960). “A note on the oxidative deamination of isomers of 5-hydroxytryptamine and other indolealkylamines”. The Journal of Pharmacy and Pharmacology. 12: 761–764. doi:10.1111/j.2042-7158.1960.tb12743.x. PMID 13697284.
  6. ^ 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.
  7. ^ Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
  8. ^ 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.
  9. ^ 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.
  10. ^ Lavaud C, Massiot G (2017). “The Iboga Alkaloids” (PDF). Progress in the Chemistry of Organic Natural Products. 105: 89–136. doi:10.1007/978-3-319-49712-9_2. ISBN 978-3-319-49711-2. PMID 28194562.
  11. ^ 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.
  12. ^ 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.
  13. ^ 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.