2-Methyltryptamine

Last updated

2-Methyltryptamine
2-Methyltryptamine.svg
Clinical data
Other names2-MT; 2-Me-T; 2-Methyl-T
Drug class Serotonin receptor agonist
Identifiers
  • 2-(2-methyl-1H-indol-3-yl)ethanamine
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.018.498 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C11H14N2
Molar mass 174.247 g·mol−1
3D model (JSmol)
  • CC1=C(C2=CC=CC=C2N1)CCN
  • 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

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]

Contents

Pharmacology

2-MT shows affinity (Ki) for the serotonin 5-HT1A and 5-HT2A receptors, with Ki 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-HT1A and 5-HT2A receptors, with EC50 Tooltip 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-HT2A 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]

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:

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

References

  1. 1 2 3 4 5 Abiero A, Ryu IS, Botanas CJ, Custodio RJ, Sayson LV, Kim M, et al. (January 2020). "Four Novel Synthetic Tryptamine Analogs Induce Head-Twitch Responses and Increase 5-HTR2a in the Prefrontal Cortex in Mice". Biomolecules & Therapeutics. 28 (1): 83–91. doi:10.4062/biomolther.2019.049. PMC   6939696 . PMID   31230432.
  2. 1 2 3 4 Chen X, Li J, Yu L, Maule F, Chang L, Gallant JA, et al. (October 2023). "A cane toad (Rhinella marina) N-methyltransferase converts primary indolethylamines to tertiary psychedelic amines". The Journal of Biological Chemistry. 299 (10): 105231. doi: 10.1016/j.jbc.2023.105231 . PMC   10570959 . PMID   37690691.
  3. 1 2 3 4 5 6 7 8 9 Chen X, Li J, Yu L, Dhananjaya D, Maule F, Cook S, et al. (10 March 2023), Bioproduction platform using a novel cane toad (Rhinella marina) N-methyltransferase for psychedelic-inspired drug discovery (PDF), doi: 10.21203/rs.3.rs-2667175/v1 , retrieved 17 March 2025
  4. 1 2 3 4 Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252.
  5. ↑ Klein LM, Cozzi NV, Daley PF, Brandt SD, Halberstadt AL (November 2018). "Receptor binding profiles and behavioral pharmacology of ring-substituted N,N-diallyltryptamine analogs". Neuropharmacology. 142: 231–239. doi:10.1016/j.neuropharm.2018.02.028. PMC   6230509 . PMID   29499272.
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