7-Methyltryptamine

7-Methyltryptamine
Clinical data
Other names7-Methyl-T; 7-MT; 7-Me-T; PAL-286; PAL286
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonin releasing agent
ATC code
  • None
Identifiers
  • 2-(7-methyl-1H-indol-3-yl)ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.034.983 Edit this at Wikidata
Chemical and physical data
FormulaC11H14N2
Molar mass174.247 g·mol−1
3D model (JSmol)
  • CC1=C2C(=CC=C1)C(=CN2)CCN
  • InChI=1S/C11H14N2/c1-8-3-2-4-10-9(5-6-12)7-13-11(8)10/h2-4,7,13H,5-6,12H2,1H3
  • Key:SGGBZKQTWMKXHD-UHFFFAOYSA-N

7-Methyltryptamine (7-Me-T or 7-methyl-T; developmental code name PAL-286) is a serotonin receptor modulator and monoamine releasing agent of the tryptamine family. It is the 7-methyl derivative of tryptamine.

The drug acts as a potent full agonist of the serotonin 5-HT2A receptor, with an EC50Tooltip half-maximal effective concentration of 44.7 nM and an EmaxTooltip maximal efficacy of 103%. It shows 6-fold lower potency as a serotonin 5-HT2A receptor agonist compared to tryptamine itself. 7-Methyltryptamine also shows affinity for the serotonin 5-HT1D receptor, but has greatly reduced affinity compared to tryptamine (IC50Tooltip half-maximal inhibitory concentration = 1,900 nM and 57 nM, respectively; 33-fold lower). It shows extremely weak affinity for the dizocilpine (MK-801) site of the NMDA receptor (IC50 = ~650,000 nM). In addition to its serotonin 5-HT2A receptor agonism, 7-methyltryptamine is a serotonin releasing agent (SRA), with EC50 values for induction of monoamine release of 23.7 nM for serotonin, 3,380 nM for dopamine, and >10,000 nM for norepinephrine in rat brain synaptosomes.

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. However, given intravenously at sufficiently high doses, tryptamine is still known to be able to produce weak and short-lived psychoactive effects in humans.

The chemical synthesis of 7-methyltryptamine has been described. The chemical identification of 7-methyltryptamine has been described as well.

7-Methyltryptamine was first described in the scientific literature by 1956. Its pharmacology was subsequently assessed in greater detail in 2014.

See also

References

  1. 1 2 3 4 5 6 7 8 Blough BE, Landavazo A, Partilla JS, Decker AM, Page KM, Baumann MH, et al. (October 2014). "Alpha-ethyltryptamines as dual dopamine-serotonin releasers". Bioorganic & Medicinal Chemistry Letters. 24 (19): 4754–4758. doi:10.1016/j.bmcl.2014.07.062. PMC 4211607. PMID 25193229.
  2. ↑ Peroutka SJ, McCarthy BG, Guan XM (1991). "5-benzyloxytryptamine: a relatively selective 5-hydroxytryptamine 1D/1B agent". Life Sciences. 49 (6): 409–418. doi:10.1016/0024-3205(91)90582-v. PMID 1650872.
  3. ↑ Berger ML (December 2000). "Tryptamine derivatives as non-competitive N-methyl-D-aspartate receptor blockers: studies using [(3)H]MK-801 binding in rat hippocampal membranes". Neuroscience Letters. 296 (1): 29–32. doi:10.1016/s0304-3940(00)01614-1. PMID 11099826.
  4. ↑ Kloda A, Adams DJ (February 2005). "Voltage-dependent inhibition of recombinant NMDA receptor-mediated currents by 5-hydroxytryptamine". British Journal of Pharmacology. 144 (3): 323–330. doi:10.1038/sj.bjp.0706049. PMC 1576009. PMID 15655527.
  5. ↑ James KM, Bryan-Lluka LJ (July 1997). "Efflux studies allow further characterisation of the noradrenaline and 5-hydroxytryptamine transporters in rat lungs". Naunyn-Schmiedeberg's Archives of Pharmacology. 356 (1): 126–133. doi:10.1007/pl00005019. PMID 9228199.
  6. ↑ Chang AS, Chang SM, Starnes DM (November 1993). "Structure-activity relationships of serotonin transport: relevance to nontricyclic antidepressant interactions". European Journal of Pharmacology. 247 (3): 239–248. doi:10.1016/0922-4106(93)90191-b. PMID 8307097.
  7. ↑ Wölfel R, Graefe KH (February 1992). "Evidence for various tryptamines and related compounds acting as substrates of the platelet 5-hydroxytryptamine transporter". Naunyn-Schmiedeberg's Archives of Pharmacology. 345 (2): 129–136. doi:10.1007/BF00165727. PMID 1570019.
  8. ↑ Ross SB, Renyi AL (September 1969). "Inhibition of the uptake of tritiated 5-hydroxytryptamine in brain tissue". European Journal of Pharmacology. 7 (3): 270–277. doi:10.1016/0014-2999(69)90091-0. PMID 5351984.
  9. ↑ Jones RS (1982). "Tryptamine: a neuromodulator or neurotransmitter in mammalian brain?". Progress in Neurobiology. 19 (1–2): 117–139. doi:10.1016/0301-0082(82)90023-5. PMID 6131482.
  10. 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."
  11. ↑ 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.
  12. ↑ 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.
  13. ↑ 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. 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.
  14. ↑ 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.
  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. 1 2 Abramovitch RA (1956). "881. Tryptamines, carbolines, and related compounds. Part III. 1-Methyl- and 1 : N-dimethyl-tryptamines". Journal of the Chemical Society (Resumed): 4593. doi:10.1039/jr9560004593. ISSN 0368-1769.
  18. ↑ Mesley RJ, Evans WH (May 1970). "Infrared identification of some hallucinogenic derivatives of tryptamine and amphetamine". The Journal of Pharmacy and Pharmacology. 22 (5): 321–332. doi:10.1111/j.2042-7158.1970.tb08533.x. PMID 4392990.
  19. ↑ Alliston GV, Bartlett AF, Maunder MJ, Phillips GF (January 1971). "An improved field test for hallucinogens". The Journal of Pharmacy and Pharmacology. 23 (1): 71–72. doi:10.1111/j.2042-7158.1971.tb12788.x. PMID 4395899.