6-Hydroxytryptamine

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6-Hydroxytryptamine
Clinical data
Other names6-Hydroxy-T; 6-HT; 6-HO-T; 6-OH-T
Drug classSerotonin receptor modulator
ATC code
  • None
Identifiers
  • 3-(2-aminoethyl)-1H-indol-6-ol
CAS Number
PubChem CID
ChemSpider
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC10H12N2O
Molar mass176.219 g·mol−1
3D model (JSmol)
  • C1=CC2=C(C=C1O)NC=C2CCN
  • InChI=1S/C10H12N2O/c11-4-3-7-6-12-10-5-8(13)1-2-9(7)10/h1-2,5-6,12-13H,3-4,11H2
  • Key:WZTKTNRVJAMKAS-UHFFFAOYSA-N

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

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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

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

Derivatives

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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

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References

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