1-Methyltryptamine

1-Methyltryptamine (1-methyl-T, 1-MT or 1-Me-T; code name PAL-637) is a serotonin receptor agonist and monoamine releasing agent of the tryptamine family.^[1][2][3] It is the 1-methyl derivative of tryptamine (T; PAL-235).^[1][2][3]

1-Methyltryptamine

Clinical data
Other names	1-Methyl-T; 1-MT; 1-Me-T; 1-Me-tryptamine; PAL-637; PAL637
Drug class	Serotonin receptor agonist; Serotonin releasing agent
Identifiers
IUPAC name 2-(1-methylindol-3-yl)ethanamine
CAS Number	7518-21-0 7088-88-2
PubChem CID	23492
ChemSpider	21963
ChEBI	CHEBI:125627
ChEMBL	ChEMBL3330641
CompTox Dashboard (EPA)	DTXSID80991164
ECHA InfoCard	100.028.525
Chemical and physical data
Formula	C11H14N2
Molar mass	174.247 g·mol−1
3D model (JSmol)	Interactive image
SMILES CN1C=C(C2=CC=CC=C21)CCN
InChI InChI=1S/C11H14N2/c1-13-8-9(6-7-12)10-4-2-3-5-11(10)13/h2-5,8H,6-7,12H2,1H3 Key:CAAGZPJPCKMFBD-UHFFFAOYSA-N

The drug is known to act as a serotonin 5-HT_2A receptor agonist (K_i = 473 nM; EC₅₀Tooltip half-maximal effective concentration = 209–4,560 nM; E_maxTooltip maximal efficacy = 55–99%), as a serotonin releasing agent (EC₅₀ = 53.1 nM), and to be inactive in inducing the release of norepinephrine and dopamine (EC₅₀ = >10,000 nM).^[1] Its activities at other serotonin receptors were not reported.^[1][3] 1-Methyltryptamine shows dramatically reduced affinity and activational potency as well as reduced efficacy at the serotonin 5-HT_2A receptor compared to tryptamine (which showed K_i = 13.1 nM; EC₅₀ = 7.36–99 nM; E_max = 101–104%).^[3][1] It also shows slightly reduced potency as a serotonin releasing agent and abolished activity as a releaser of norepinephrine and dopamine relative to tryptamine (which had EC₅₀ = 32.6 nM, 716 nM, and 164 nM, respectively).^[1]

Analogues of 1-methyltryptamine, like 1-methylserotonin and 1-iPr-5-MeO-T, have been studied.^[4] Similarly to the case of 1-methyltryptamine contrasted with tryptamine, they show dramatically reduced affinities and activational potencies at the human serotonin 5-HT_2A receptor relative to their 1-unsubstituted counterparts (serotonin and 5-methoxytryptamine, respectively).^[4]

See also

• 1-Methylpsilocin
• Lespedamine (1-methoxy-DMT)
• 1-Propyl-5-MeO-AMT
• O-4310 (1-isopropyl-6-fluoropsilocin)
• CP-132,484
• 2-Methyltryptamine
• 5-Methyltryptamine