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4-Methoxytryptamine

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4-Methoxytryptamine
Clinical data
Other names4-Methoxytryptamine; 4-Methoxy-T; 4-MeO-T; PAL-548; PAL548
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist
ATC code
  • None
Identifiers
  • 2-(4-methoxy-1H-indol-3-yl)ethanamine
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC11H14N2O
Molar mass190.246 g·mol−1
3D model (JSmol)
  • COC1=CC=CC2=C1C(=CN2)CCN
  • 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

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]

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%.[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]

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

See also

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References

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  1. ^ a b c d Blough BE, Landavazo A, Partilla JS, Decker AM, Page KM, Baumann MH, Rothman RB (October 2014). "Alpha-ethyltryptamines as dual dopamine-serotonin releasers". Bioorg Med Chem Lett. 24 (19): 4754–4758. doi:10.1016/j.bmcl.2014.07.062. PMC 4211607. PMID 25193229.
  2. ^ Curtis DR, Davis R (April 1962). "Pharmacological studies upon neurones of the lateral geniculate nucleus of the cat". Br J Pharmacol Chemother. 18 (2): 217–246. doi:10.1111/j.1476-5381.1962.tb01404.x. PMC 1482133. PMID 13882768.
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