5-Methyltryptamine

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5-Methyltryptamine
5-Methyltryptamine.svg
Clinical data
Other names5-MeT; 5-Me-T; 5-Methyl-T; 5-MT; PAL-22; PAL22; NSC-90805; NSC90805
Drug class Serotonin receptor agonist; Serotonin releasing agent
Identifiers
  • 2-(5-methyl-1H-indol-3-yl)ethanamine
CAS Number
PubChem CID
ChemSpider
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C11H14N2
Molar mass 174.247 g·mol−1
3D model (JSmol)
  • CC1=CC2=C(C=C1)NC=C2CCN
  • InChI=1S/C11H14N2/c1-8-2-3-11-10(6-8)9(4-5-12)7-13-11/h2-3,6-7,13H,4-5,12H2,1H3
  • Key:PYOUAIQXJALPKW-UHFFFAOYSA-N

5-Methyltryptamine (5-MeT, 5-Me-T) is a non-selective serotonin receptor agonist and serotonin releasing agent of the tryptamine family that has been used in scientific research. [1] [2] It is related to other 5-substituted tryptamines such as serotonin (5-hydroxytryptamine; 5-HT) and 5-methoxytryptamine (5-MeO-T). [1] [2] The compound is also a positional isomer of N-methyltryptamine (NMT). [1]

Contents

Pharmacology

5-MeT is known to act as a potent serotonin 5-HT2A receptor full agonist, with an EC50 Tooltip half-maximal effective concentration of 6.00 nM and an Emax Tooltip maximal efficacy of 100%. [1] In addition, it is known to be a ligand of the serotonin 5-HT1A [3] and 5-HT2B receptors [2] and an agonist of the serotonin 5-HT1D [4] [5] and 5-HT2C receptors. [6] [7] [8] Similarly to tryptamine and 5-MeO-T, but in contrast to serotonin, 5-MeT shows very low potency as an agonist of the serotonin 5-HT3 receptor (EC50 = 60,000 nM). [9]

In addition to acting as an agonist of various serotonin receptors, 5-MeT is a monoamine releasing agent (MRA), with high selectivity for induction of serotonin release over induction of dopamine and norepinephrine release (EC50 = 139 nM, >10,000 nM, and >10,000 nM, respectively, in rat brain synaptosomes). [1] However, its potency for induction of serotonin release in this system is 23-fold lower than its potency as a serotonin 5-HT2A receptor agonist. [1]

Tryptamines without substitutions at the amine or alpha carbon, such as tryptamine, serotonin, and 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. [10] [11] [12] [13] [14] [2] [15] However, given intravenously at sufficiently high doses, tryptamine is still known to be able to produce weak and short-lived serotonergic psychedelic effects in humans. [16] [11] [1] [15]

Chemistry

The predicted log P of 5-MeT is 1.84 to 1.9. [17] [18]

See also

References

  1. 1 2 3 4 5 6 7 Blough BE, Landavazo A, Partilla JS, Decker AM, Page KM, Baumann MH, et al. (October 2014). "Alpha-ethyltryptamines as dual dopamine-serotonin releasers". Bioorg Med Chem Lett. 24 (19): 4754–4758. doi:10.1016/j.bmcl.2014.07.062. PMC   4211607 . PMID   25193229.
  2. 1 2 3 4 Boess FG, Martin IL (1994). "Molecular biology of 5-HT receptors". Neuropharmacology. 33 (3–4): 275–317. doi:10.1016/0028-3908(94)90059-0. PMID   7984267.
  3. ↑ Soblosky JS, Dills C, DuMontier G, Jeng I (May 1987). "Evidence for 5-HT1A binding sites in chick embryo brain and discrimination by 5-methoxytryptamine". Biochem Int. 14 (5): 797–803. PMID   2970262.
  4. ↑ Cushing DJ, Baez M, Kursar JD, Schenck K, Cohen ML (1994). "Serotonin-induced contraction in canine coronary artery and saphenous vein: role of a 5-HT1D-like receptor". Life Sci. 54 (22): 1671–1680. doi:10.1016/0024-3205(94)00607-5. PMID   7909909.
  5. ↑ Uchiyama-Tsuyuki Y, Saitoh M, Muramatsu M (1996). "Identification and characterization of the 5-HT4 receptor in the intestinal tract and striatum of the guinea pig". Life Sci. 59 (25–26): 2129–2137. doi:10.1016/s0024-3205(96)00569-3. PMID   8950316.
  6. ↑ Watts SW, Cohen ML (January 1993). "Further evidence that the guinea pig tracheal contractile serotonergic receptor is a 5-hydroxytryptamine2 receptor: use of 5-methyltryptamine and dipropyl-5-carboxamidotryptamine". J Pharmacol Exp Ther. 264 (1): 271–275. doi:10.1016/S0022-3565(25)10263-2. PMID   8423530.
  7. ↑ Garro MA, López de Jesús M, Ruíz de Azúa I, Callado LF, Meana JJ, Sallés J (April 2001). "Regulation of phospholipase Cbeta activity by muscarinic acetylcholine and 5-HT(2) receptors in crude and synaptosomal membranes from human cerebral cortex". Neuropharmacology. 40 (5): 686–95. doi:10.1016/s0028-3908(00)00206-9. PMID   11311896.
  8. ↑ van Wijngaarden I, Soudijn W (1997). "5-HT2A, 5-HT2B and 5-HT2C receptor ligands". Pharmacochemistry Library. Vol. 27. Elsevier. p. 161–197. doi:10.1016/s0165-7208(97)80013-x. ISBN   978-0-444-82041-9.
  9. ↑ Bower KS, Price KL, Sturdee LE, Dayrell M, Dougherty DA, Lummis SC (February 2008). "5-Fluorotryptamine is a partial agonist at 5-HT3 receptors, and reveals that size and electronegativity at the 5 position of tryptamine are critical for efficient receptor function". Eur J Pharmacol. 580 (3): 291–297. doi:10.1016/j.ejphar.2007.11.014. PMC   2649378 . PMID   18082160.
  10. ↑ Jones RS (1982). "Tryptamine: a neuromodulator or neurotransmitter in mammalian brain?". Prog Neurobiol. 19 (1–2): 117–139. doi:10.1016/0301-0082(82)90023-5. PMID   6131482.
  11. 1 2 Shulgin A (1997). Tihkal: The Continuation. Transform Press. #53. T. ISBN   978-0-9630096-9-2 . Retrieved 17 August 2024. (with 250 mg, intravenously) "Tryptamine was infused intravenously over a period of up to 7.5 minutes. Physical changes included an increases in blood pressure, in the amplitude of the patellar reflex, and in pupillary diameter. The subjective changes are not unlike those seen with small doses of LSD. A point-by-point comparison between the tryptamine and LSD syndromes reveals a close similarity which is consistent with the hypothesis that tryptamine and LSD have a common mode of action."
  12. ↑ Nichols DE (2012). "Structure–activity relationships of serotonin 5-HT2A agonists". Wiley Interdisciplinary Reviews: Membrane Transport and Signaling. 1 (5): 559–579. doi: 10.1002/wmts.42 . ISSN   2190-460X.
  13. ↑ Nichols DE (2018). Chemistry and Structure-Activity Relationships of Psychedelics. Current Topics in Behavioral Neurosciences. Vol. 36. pp. 1–43. doi:10.1007/7854_2017_475. ISBN   978-3-662-55878-2. PMID   28401524.
  14. ↑ Prozialeck WC, Vogel WH (February 1979). "MAO inhibition and the effects of centrally administered LSD, serotonin, and 5-methoxytryptamine on the conditioned avoidance response in rats". Psychopharmacology (Berl). 60 (3): 309–310. doi:10.1007/BF00426673. PMID   108709. In contrast, MAO inhibition greatly increased brain levels of 5-HT and 5-MT (Prozialeck and Vogel, 1978). For instance, clorgyline and deprenyl increased brain levels of 5-HT 8.5-fold and 4.4-fold and of 5-MT 20-fold and 5-fold, respectively.
  15. 1 2 Martin WR, Sloan JW (1970). "Effects of infused tryptamine in man". Psychopharmacologia. 18 (3): 231–237. doi:10.1007/BF00412669. PMID   4922520.
  16. ↑ Martin WR, Sloan JW (1977). "Pharmacology and Classification of LSD-like Hallucinogens". Drug Addiction II. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 305–368. doi:10.1007/978-3-642-66709-1_3. ISBN   978-3-642-66711-4. MARTIN and SLOAN (1970) found that intravenously infused tryptamine increased blood pressure, dilated pupils, enhanced the patellar reflex, and produced perceptual distortions. [...] Tryptamine, but not DMT, increases locomotor activity in the mouse, while both antagonize reserpine depression (V ANE et al., 1961). [...] In the rat, tryptamine causes backward locomotion, Straub tail, bradypnea and dyspnea, and clonic convulsions (TEDESCHI et al., 1959). [...] Tryptamine produces a variety of changes in the cat causing signs of sympathetic activation including mydriasis, retraction of nictitating membrane, piloerection, motor signs such as extension of limbs and convulsions and affective changes such as hissing and snarling (LAIDLAW, 1912). [...]
  17. ↑ "5-Methyltryptamine". PubChem. Retrieved 15 January 2025.
  18. ↑ "5-methyltryptamine". ChemSpider. 10 June 2024. Retrieved 15 January 2025.
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