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4-Methoxytryptamine

4-Methoxytryptamine (4-MeO-T; developmental code name PAL-548) is a serotonin receptor modulator of the tryptamine and 4-hydroxytryptamine families. It is the O-methyl derivative of 4-hydroxytryptamine (4-HT) and a positional isomer of 5-methoxytryptamine and 6-methoxytryptamine.

Column 1
4-Methoxytryptamine; 4-Methoxy-T; 4-MeO-T; PAL-548; PAL548
Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist
.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}None
IUPAC name
2-(4-methoxy-1H-indol-3-yl)ethanamine
3610-35-3
19219
18136
ChEMBL343529
DTXSID70189679
C11H14N2O
190.246 g·mol−1
Interactive image
SMILES
COC1=CC=CC2=C1C(=CN2)CCN
InChI
InChI=1S/C11H14N2O/c1-14-10-4-2-3-9-11(10)8(5-6-12)7-13-9/h2-4,7,13H,5-6,12H2,1H3Key:WMBARRJMPVVQEZ-UHFFFAOYSA-N

4-Methoxytryptamine (4-MeO-T; developmental code name PAL-548) is a serotonin receptor modulator of the tryptamine and 4-hydroxytryptamine families. It is the O-methyl derivative of 4-hydroxytryptamine (4-HT) and a positional isomer of 5-methoxytryptamine and 6-methoxytryptamine.

The drug has been found to act as a potent serotonin 5-HT2A receptor full agonist, with an EC50Tooltip half-maximal effective concentration of 9.02 nM and an EmaxTooltip half-maximal effective concentration of 108%. It was inactive as a monoamine releasing agent, including of serotonin, norepinephrine, and dopamine, in rat brain synaptosomes (all EC50 = >10,000 nM), but was a very low-potency serotonin reuptake inhibitor (IC50Tooltip half-maximal effective concentration = 4,114 nM).

4-Methoxytryptamine was first described in the scientific literature by at least 1962.

  • Substituted tryptamine

  • 4-Hydroxytryptamine

  • 5-Methoxytryptamine

  • 6-Methoxytryptamine

  • 4-MeO-DMT

  • 4-MeO-T - Isomer Design

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