Chemistry:7-Methoxytryptamine

From HandWiki

7-Methoxytryptamine (7-MeO-T or 7-methoxy-T; developmental code name PAL-533) is a serotonin receptor modulator and monoamine releasing agent of the tryptamine family.[1][2] It is the 7-methoxy derivative of tryptamine.[1]

The drug acts as a full agonist of the serotonin 5-HT2A receptor, with an EC50 of 496 nM and an Emax of 107%.[1] It shows 67-fold lower potency as a serotonin 5-HT2A receptor agonist compared to tryptamine itself.[1] In addition to its serotonin 5-HT2A receptor agonism, 7-methoxytryptamine is a serotonin releasing agent (SRA), with EC50 values for induction of monoamine release of 44.6 nM for serotonin, 2,118 nM for dopamine, and 5,600 nM for norepinephrine in rat brain synaptosomes.[1] The effects of 7-methoxytryptamine in rodents have been described.[3][4]

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.[5][6][7][8][9][10][11] However, given intravenously at sufficiently high doses, tryptamine is still known to be able to produce weak and short-lived psychoactive effects in humans.[12][6][1][11]

The chemical synthesis of 7-methoxytryptamine has been described.[1][13][14][3][15]

7-Methoxytryptamine was first described in the scientific literature by Ernst Späth and Edgar Lederer by 1931.[15][16] Its pharmacology was subsequently assessed in greater detail in 2014.[1]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 "Alpha-ethyltryptamines as dual dopamine-serotonin releasers". Bioorganic & Medicinal Chemistry Letters 24 (19): 4754–4758. October 2014. doi:10.1016/j.bmcl.2014.07.062. PMID 25193229. PMC 4211607. https://isomerdesign.com/bitnest/external/10.1016/j.bmcl.2014.07.062. 
  2. ↑ "Structure-Activity Relationship among Hallucinogenic Agents". Origin and Mechanisms of Hallucinations. Boston, MA: Springer US. 1970. pp. 345–376. doi:10.1007/978-1-4615-8645-6_29. ISBN 978-1-4615-8647-0. 
  3. ↑ 3.0 3.1 "7‐Methoxyindole and its Derivatives". Israel Journal of Chemistry 5 (4): 129–136. 1967. doi:10.1002/ijch.196700026. ISSN 0021-2148. 
  4. ↑ "Medicinal Chemistry and Structure-Activity Relationships of Hallucinogens". Hallucinogens: Neurochemical, Behavioral, and Clinical Perspectives. New York: Raven Press. 1984. pp. 95–142. ISBN 978-0-89004-990-7. OCLC 10324237. https://bitnest.netfirms.com/external/Books/HallucinogensNBCP95. "7-Methoxytryptamine displayed weak behavioral activity in animals (124). [...] The 6- and 7-methoxy derivatives of DMT, 71 and 72, respectively, display a low order of behavioral activity in animals (65,86,91,93,124). [...] The 6- and 7-methoxy derivatives [of DMT] are less active than either the 4- or 5-methoxy isomers." 
  5. ↑ "Tryptamine: a neuromodulator or neurotransmitter in mammalian brain?". Progress in Neurobiology 19 (1–2): 117–139. 1982. doi:10.1016/0301-0082(82)90023-5. PMID 6131482. 
  6. ↑ 6.0 6.1 Tihkal: The Continuation. Transform Press. 1997. #53. T. ISBN 978-0-9630096-9-2. https://books.google.com/books?id=jl_ik66IumUC. 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."" 
  7. ↑ "Structure–activity relationships of serotonin 5-HT2A agonists". Wiley Interdisciplinary Reviews: Membrane Transport and Signaling 1 (5): 559–579. 2012. doi:10.1002/wmts.42. ISSN 2190-460X. 
  8. ↑ Chemistry and Structure-Activity Relationships of Psychedelics. Current Topics in Behavioral Neurosciences. 36. 2018. pp. 1–43. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. 
  9. ↑ "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. February 1979. 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.". 
  10. ↑ "Molecular biology of 5-HT receptors". Neuropharmacology 33 (3–4): 275–317. 1994. doi:10.1016/0028-3908(94)90059-0. PMID 7984267. 
  11. ↑ 11.0 11.1 "Effects of infused tryptamine in man". Psychopharmacologia 18 (3): 231–237. 1970. doi:10.1007/BF00412669. PMID 4922520. 
  12. ↑ "Pharmacology and Classification of LSD-like Hallucinogens". Drug Addiction II. Berlin, Heidelberg: Springer Berlin Heidelberg. 1977. 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). [...]" 
  13. ↑ "Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents". Journal of Medicinal Chemistry 28 (7): 892–896. July 1985. doi:10.1021/jm00145a007. PMID 4009612. 
  14. ↑ "Synthesis of Vinca Alkaloids and Related Compounds. LXV. Preparation of 7-Methoxytryptamine". Synthetic Communications 23 (12): 1689–1698. 1993. doi:10.1080/00397919308011267. ISSN 0039-7911. 
  15. ↑ 15.0 15.1 "Synthesen von 4‐Carbolinen". Berichte der deutschen chemischen Gesellschaft (A and B Series) 63 (8): 2102–2111. 17 September 1930. doi:10.1002/cber.19300630839. ISSN 0365-9488. 
  16. ↑ "The synthesis of some indol derivatives". Canadian Journal of Research 4 (6): 591–595. 1 June 1931. doi:10.1139/cjr31-047. ISSN 1923-4287. 



Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:7-Methoxytryptamine&oldid=4434004"