6-Methoxytryptamine

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]

6-Methoxytryptamine

Clinical data
Other names	6-Methoxy-T; 6-MeO-T; PAL-263; PAL263
Drug class	Monoamine releasing agent; Serotonin–norepinephrine–dopamine releasing agent; Serotonin receptor modulator
ATC code	None
Identifiers
IUPAC name 2-(6-methoxy-1H-indol-3-yl)ethanamine
CAS Number	3610-36-4 Y
PubChem CID	17654
ChemSpider	16687
UNII	83E56U9G2L
ChEMBL	ChEMBL337825
CompTox Dashboard (EPA)	DTXSID80189680
ECHA InfoCard	100.020.708
Chemical and physical data
Formula	C11H14N2O
Molar mass	190.246 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=CC2=C(C=C1)C(=CN2)CCN
InChI InChI=1S/C11H14N2O/c1-14-9-2-3-10-8(4-5-12)7-13-11(10)6-9/h2-3,6-7,13H,4-5,12H2,1H3 Key:VOCGEKMEZOPDFP-UHFFFAOYSA-N

Pharmacology

6-Methoxytryptamine is a potent serotonin–norepinephrine–dopamine releasing agent (SNDRA), with EC₅₀Tooltip half-maximal effective concentration 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-HT_2A receptor, but with very low potency; its EC₅₀ and E_maxTooltip maximal efficacy 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-HT_2A receptor agonist, while 5-methoxytryptamine was the most potent serotonin 5-HT_2A receptor agonist, with 5-methoxytryptamine showing approximately 4,857-fold higher potency in terms of serotonin 5-HT_2A 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

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