4-Methoxytryptamine

4-Methoxytryptamine (4-MeO-T; developmental code name PAL-548) is a serotonin receptor modulator of the tryptamine and 4-hydroxytryptamine families.^[1] It is the O-methyl derivative of 4-hydroxytryptamine (4-HT) and a positional isomer of 5-methoxytryptamine and 6-methoxytryptamine.^[1]

4-Methoxytryptamine

Clinical data
Other names	4-Methoxytryptamine; 4-Methoxy-T; 4-MeO-T; PAL-548; PAL548
Drug class	Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist
ATC code	None
Identifiers
IUPAC name 2-(4-methoxy-1H-indol-3-yl)ethanamine
CAS Number	3610-35-3
PubChem CID	19219
ChemSpider	18136
ChEMBL	ChEMBL343529
CompTox Dashboard (EPA)	DTXSID70189679
Chemical and physical data
Formula	C11H14N2O
Molar mass	190.246 g·mol−1
3D model (JSmol)	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,5-6,12H2,1H3 Key:WMBARRJMPVVQEZ-UHFFFAOYSA-N

Pharmacology

The drug has been found to act as a potent serotonin 5-HT_2A receptor full agonist, with an EC₅₀Tooltip half-maximal effective concentration of 9.02 nM and an E_maxTooltip half-maximal effective concentration of 108%.^[1] 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).^[1]

History

4-Methoxytryptamine was first described in the scientific literature by at least 1962.^[2]

See also

• Substituted tryptamine
• 4-Hydroxytryptamine
• 5-Methoxytryptamine
• 6-Methoxytryptamine
• 4-MeO-DMT