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6-Methyltryptamine

6-Methyltryptamine (6-Me-T or 6-methyl-T; developmental code name PAL-522) is a serotonin receptor modulator and monoamine releasing agent of the tryptamine family. It is the 6-methyl derivative of tryptamine.


Column 1
6-Methyl-T; 6-MT; 6-Me-T; PAL-522; PAL522
Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonin–dopamine releasing agent
.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-(6-methyl-1H-indol-3-yl)ethanamine
62500-90-7
190006
165022
CHEBI:125623
ChEMBL3330642
DTXSID00978098
C11H14N2
174.247 g·mol−1
Interactive image
SMILES
CC1=CC2=C(C=C1)C(=CN2)CCN
InChI
InChI=1S/C11H14N2/c1-8-2-3-10-9(4-5-12)7-13-11(10)6-8/h2-3,6-7,13H,4-5,12H2,1H3Key:GEVXFHYJXGYXJP-UHFFFAOYSA-N

6-Methyltryptamine (6-Me-T or 6-methyl-T; developmental code name PAL-522) is a serotonin receptor modulator and monoamine releasing agent of the tryptamine family. It is the 6-methyl derivative of tryptamine.

The drug acts as a potent full agonist of the serotonin 5-HT2A receptor, with an EC50Tooltip half-maximal effective concentration of 75.3 nM and an EmaxTooltip maximal efficacy of 110%. It is about 10-fold less potent as a serotonin 5-HT2A receptor agonist than tryptamine itself. In addition to its serotonin 5-HT2A receptor agonism, 6-methyltryptamine is a serotonin–dopamine releasing agent (SDRA), with EC50 values for induction of monoamine release of 51.6 nM for serotonin, 353 nM for dopamine, and >10,000 nM for norepinephrine in rat brain synaptosomes. It shows extremely weak affinity for the dizocilpine (MK-801) site of the NMDA receptor (IC50Tooltip half-maximal inhibitory concentration = 175,000–260,000 nM).

Tryptamines without substitutions at the amine or alpha carbon, such as tryptamine, serotonin (5-hydroxytryptamine; 5-HT), and 5-methoxytryptamine (5-MeO-T), are known to be very rapidly metabolized and thereby inactivated by monoamine oxidase A (MAO-A) in vivo and to have very short elimination half-lives. However, given intravenously at sufficiently high doses, tryptamine is still known to be able to produce weak and short-lived psychoactive effects in humans.

The chemical synthesis of 6-methyltryptamine has been described.

6-Methyltryptamine was first described in the scientific literature by 1965. Its pharmacology was subsequently assessed in greater detail in 2014.

  • Substituted tryptamine

  • 6-Methyl-DMT

  • 6-Methyl-5-MeO-DMT

  • 6-Methoxytryptamine

  • 6-Hydroxytryptamine

  • 6-Fluorotryptamine

  • 6-Bromotryptamine

  • 6-Methyl-T - Isomer Design

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