6-Hydroxytryptamine

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]

6-Hydroxytryptamine

Clinical data
Other names	6-Hydroxy-T; 6-HT; 6-HO-T; 6-OH-T
Drug class	Serotonin receptor modulator
ATC code	None
Identifiers
IUPAC name 3-(2-aminoethyl)-1H-indol-6-ol
CAS Number	443-31-2
PubChem CID	160463
ChemSpider	141007
ChEMBL	ChEMBL19264
CompTox Dashboard (EPA)	DTXSID10196105
Chemical and physical data
Formula	C10H12N2O
Molar mass	176.219 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1=CC2=C(C=C1O)NC=C2CCN
InChI 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

Pharmacology

6-Hydroxytryptamine shows dramatically reduced affinity for serotonin receptors, including the serotonin 5-HT_1A, 5-HT_1B, 5-HT_2A, and 5-HT_2C receptors (K_i = 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

• Substituted tryptamine
• 4-Hydroxytryptamine
• 6-Methoxytryptamine
• 6-Hydroxy-DMT
• 6-MeO-DMT
• 5-MeO-isoDMT
• Zalsupindole (DLX-001, AAZ-A-154)