2-Methyltryptamine

2-Methyltryptamine (2-MT, 2-Me-T, or 2-methyl-T) is a serotonin receptor agonist of the tryptamine family.^[1][2][3] It shows dramatically reduced activity at serotonin receptors compared to tryptamine^[2][3] and mixed effects in terms of psychedelic-like effects in animals.^[1][3]

2-Methyltryptamine

Clinical data
Other names	2-MT; 2-Me-T; 2-Methyl-T
Drug class	Serotonin receptor agonist
Identifiers
IUPAC name 2-(2-methyl-1H-indol-3-yl)ethanamine
CAS Number	2731-06-8
PubChem CID	75949
ChemSpider	68452
ChEMBL	ChEMBL2358910
CompTox Dashboard (EPA)	DTXSID30181755
ECHA InfoCard	100.018.498
Chemical and physical data
Formula	C11H14N2
Molar mass	174.247 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=C(C2=CC=CC=C2N1)CCN
InChI InChI=1S/C11H14N2/c1-8-9(6-7-12)10-4-2-3-5-11(10)13-8/h2-5,13H,6-7,12H2,1H3 Key:CPVSLHQIPGTMLH-UHFFFAOYSA-N

Pharmacology

2-MT shows affinity (K_i) for the serotonin 5-HT_1A and 5-HT_2A receptors, with K_i values of 1,095 nM and 7,774 nM, respectively.^[2][3] These affinities were respectively 34-fold and 3.2-fold lower than those of tryptamine in the same study.^[2][3] It also acts as an agonist of the serotonin 5-HT_1A and 5-HT_2A receptors, with EC₅₀Tooltip half-maximal effective concentration values of 12,534 nM and 4,598 nM, respectively.^[3] These activational potencies were respectively 14-fold and 19-fold lower than those of tryptamine in the same study.^[3]

It does not produce conditioned place preference (CPP), self-administration, or changes in locomotor activity in rodents.^[1] Findings on whether 2-MT produces the head-twitch response (HTR), a behavioral proxy of psychedelic effects, are mixed.^[1][3] In one study, it produced the HTR at a dose of 3 mg/kg intraperitoneally, and this was completely blocked by the serotonin 5-HT_2A receptor antagonist ketanserin.^[1] In another study, both tryptamine and 2-MT did not produce the HTR at a dose of 3 mg/kg intraperitoneally.^[3]

Chemistry

Derivatives

A number of derivatives of 2-MT are known, including:^[4]

• 2,α-Dimethyltryptamine (2,α-DMT or 2-Me-αMT)
• 2,N,N-Trimethyltryptamine (2,N,N-TMT or 2-Me-DMT)
• 2-Methyl-N,N-diethyltryptamine (2-Me-DET)
• 5-Methoxy-2,N,N-trimethyltryptamine (5-MeO-2,N,N-TMT or 2-Me-5-MeO-DMT)

These drugs were synthesized and tested by Alexander Shulgin.^[4] He found that the drugs in this group became orally active but generally produced no or only mild psychedelic effects (with the exception of 2-Me-5-MeO-DMT).^[4] Instead, they caused effects like tactile enhancement and auditory distortion, among others.^[4]

A couple of other derivatives, 2-methyl-5-MeO-DALT and 2-methyl-5-F-DALT, are also known.^[5]

Further derivatives of 2-MT include the following:

• 2-Methyl-5-HT (a moderately selective serotonin 5-HT₃ receptor full agonist)
• 2-Methyl-5-chloro-DMT (ST-1936; a selective serotonin 5-HT₆ receptor agonist)
• 2-Ethyl-5-methoxy-DMT (EMDT; a selective serotonin 5-HT₆ receptor agonist)

EMD-386088 (2-methyl-5-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole) isn't technically a tryptamine but is very similar and is a serotonin 5-HT₆ receptor partial agonist as well as having moderate affinity for the serotonin 5-HT₃ receptor and acting as a dopamine reuptake inhibitor.

Yet another related compound is 2-HO-NMT, a tryptamine alkaloid.

See also

• 1-Methyltryptamine
• 5-Methyltryptamine