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.^[1] It is the 6-methyl derivative of tryptamine.^[1]

Other names6-Methyl-T; 6-MT; 6-Me-T; PAL-522; PAL522

Drug classSerotonin receptor modulator; Serotonin 5-HT_2A receptor agonist; Serotonin–dopamine releasing agent

ATC code

• None

CAS Number

• 62500-90-7

Quick facts Clinical data, Other names ...

6-Methyltryptamine

Clinical data
Other names	6-Methyl-T; 6-MT; 6-Me-T; PAL-522; PAL522
Drug class	Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonin–dopamine releasing agent
ATC code	None
Identifiers
IUPAC name 2-(6-methyl-1H-indol-3-yl)ethanamine
CAS Number	62500-90-7
PubChem CID	190006
ChemSpider	165022
ChEBI	CHEBI:125623
ChEMBL	ChEMBL3330642
CompTox Dashboard (EPA)	DTXSID00978098
Chemical and physical data
Formula	C11H14N2
Molar mass	174.247 g·mol−1
3D model (JSmol)	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,4-5,12H2,1H3 Key:GEVXFHYJXGYXJP-UHFFFAOYSA-N

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The drug acts as a potent full agonist of the serotonin 5-HT_2A receptor, with an EC₅₀Tooltip half-maximal effective concentration of 75.3 nM and an E_maxTooltip maximal efficacy of 110%.^[1] It is about 10-fold less potent as a serotonin 5-HT_2A receptor agonist than tryptamine itself.^[1] In addition to its serotonin 5-HT_2A 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.^[1] 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).^[2]

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.^{[3][4][5][6][7][8][9]} However, given intravenously at sufficiently high doses, tryptamine is still known to be able to produce weak and short-lived psychoactive effects in humans.^{[10][4][1][9]}

The chemical synthesis of 6-methyltryptamine has been described.^[1]

6-Methyltryptamine was first described in the scientific literature by 1965.^[11] Its pharmacology was subsequently assessed in greater detail in 2014.^[1]