It is an extremely potent serotonin 5-HT2A receptor agonist in vitro, with an EC50Tooltip half-maximal effective concentration of 0.503nM.[8] This was more potent than any other tryptamine evaluated in two large series of compounds.[8][9] For comparison, 5-MeO-DMT had an EC50 of 3.87nM (7.7-fold lower) and dimethyltryptamine (DMT) had an EC50 of 38.3nM (76-fold lower).[9]
5-MT, in contrast to the closely related melatonin, has no affinity for the melatonin receptors.[26][27] However, it may be converted into melatonin in the body, and hence may indirectly act as a melatonin receptor agonist.[3][5]
Brain levels of 5-MT following central administration of 5-MT in rats were potentiated by 20-fold by the MAO-A inhibitorclorgyline and by 5.5-fold by the MAO-B inhibitorselegiline.[13][12] Similarly, levels of serotonin and phenethylamine were also greatly elevated by these drugs.[12][13] In accordance with the potentiation of brain levels of 5-MT by MAOIs, the behavioral effects of centrally administered 5-MT in rats, for instance in the conditioned avoidance response test, are markedly enhanced by MAOIs, including by the dual MAO-A and MAO-B inhibitor iproniazid and by clorgyline and selegiline.[13]
Similarly to rat findings, pineal gland levels of endogenous 5-MT are dramatically elevated by the MAO-A inhibitor clorgyline and by the dual MAO-A and MAO-B inhibitor pargyline in hamsters, and plasma levels of exogenous 5-MT are greatly elevated by these MAOIs as well.[14] Conversely, selegiline was ineffective in elevating brain or plasma 5-MT levels in hamsters.[14]
^ abcdNichols DE (2018). "Chemistry and Structure-Activity Relationships of Psychedelics". Curr Top Behav Neurosci. 36: 1–43. doi:10.1007/7854_2017_475. PMID28401524.
^ abGalzin AM, Eon MT, Esnaud H, Lee CR, Pévet P, Langer SZ (1988). "Day-night rhythm of 5-methoxytryptamine biosynthesis in the pineal gland of the golden hamster (Mesocricetus auratus)". J. Endocrinol. 118 (3): 389–397. doi:10.1677/joe.0.1180389. PMID2460575.
^ abcdTan DX, Hardeland R, Back K, Manchester LC, Alatorre-Jimenez MA, Reiter RJ (August 2016). "On the significance of an alternate pathway of melatonin synthesis via 5-methoxytryptamine: comparisons across species". J Pineal Res. 61 (1): 27–40. doi:10.1111/jpi.12336. PMID27112772.
^ abPrzegaliński E, Zebrowska-Lupina I, Wójcik A, Kleinrok Z (1977). "5-Methoxytryptamine-induced head twitches in rats". Pol J Pharmacol Pharm. 29 (3): 253–261. PMID267911.
^ abcdGreen AR, Hughes JP, Tordoff AF (August 1975). "The concentration of 5-methoxytryptamine in rat brain and its effects on behaviour following its peripheral injection". Neuropharmacology. 14 (8): 601–606. doi:10.1016/0028-3908(75)90127-6. PMID126386.
^ abcdProzialek WC, Vogel WH (February 1978). "Deamination of 5-methoxytryptamine, serotonin and phenylethylamine by rat MAO in vitro and in vivo". Life Sci. 22 (7): 561–569. doi:10.1016/0024-3205(78)90334-x. PMID272480.
^ abcdeProzialeck 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. PMID108709. 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.
^ abcdeRaynaud F, Pévet P (February 1991). "5-Methoxytryptamine is metabolized by monoamine oxidase A in the pineal gland and plasma of golden hamsters". Neurosci Lett. 123 (2): 172–174. doi:10.1016/0304-3940(91)90923-h. PMID2027530.
^ abcVetulani J, Byrska B, Reichenberg K (1979). "Head twitches produced by serotonergic drugs and opiates after lesion of the mesostriatal serotonergic system of the rat". Pol J Pharmacol Pharm. 31 (4): 413–423. PMID316525.
^ abcKolasa K, Kleinrok Z, Rajtar G, Juszkiewicz M (1984). "Effects of histamine and H1 and H2-receptor antagonists on wet-dog-shake episodes in rats induced with tranylcypromine and 5-methoxytryptamine". Acta Physiol Pol. 35 (3): 225–230. PMID6152672.
^Volk B, Nagy BJ, Vas S, Kostyalik D, Simig G, Bagdy G (2010). "Medicinal chemistry of 5-HT5A receptor ligands: a receptor subtype with unique therapeutical potential". Curr Top Med Chem. 10 (5): 554–578. doi:10.2174/156802610791111588. PMID20166946.
^Wu PH, Gurevich N, Carlen PL (1988). "Serotonin-1A receptor activation in hippocampal CA1 neurons by 8-hydroxy-2-(di-n-propylamino)tetralin, 5-methoxytryptamine and 5-hydroxytryptamine". Neurosci. Lett. 86 (1): 72–76. doi:10.1016/0304-3940(88)90185-1. PMID2966313. S2CID21620262.
^Yamada J, Sugimoto Y, Yoshikawa T, Horisaka K (1997). "Hyperglycemia induced by the 5-HT receptor agonist, 5-methoxytryptamine, in rats: involvement of the peripheral 5-HT2A receptor". Eur J Pharmacol. 323 (2–3): 235–240. doi:10.1016/S0014-2999(97)00029-0. PMID9128844.
^Amemiya N, Hatta S, Takemura H, Ohshika H (1996). "Characterization of the contractile response induced by 5-methoxytryptamine in rat stomach fundus strips". Eur J Pharmacol. 318 (2–3): 403–409. doi:10.1016/S0014-2999(96)00777-7. PMID9016931.
^Craig DA, Eglen RM, Walsh LK, Perkins LA, Whiting RL, Clarke DE (1990). "5-Methoxytryptamine and 2-methyl-5-hydroxytryptamine-induced desensitization as a discriminative tool for the 5-HT3 and putative 5-HT4 receptors in guinea pig ileum". Naunyn-Schmiedeberg's Arch Pharmacol. 342 (1): 9–16. doi:10.1007/bf00178965. PMID2402303. S2CID24743785.
^Boess FG, Monsma Jr FJ, Carolo C, Meyer V, Rudler A, Zwingelstein C, Sleight AJ (1997). "Functional and radioligand binding characterization of rat 5-HT6 receptors stably expressed in HEK293 cells". Neuropharmacology. 36 (4–5): 713–720. doi:10.1016/S0028-3908(97)00019-1. PMID9225298. S2CID41813873.
^Glennon RA, Dukat M, Westkaemper RB (2000-01-01). "Serotonin Receptor Subtypes and Ligands". American College of Neurophyscopharmacology. Archived from the original on 21 April 2008. Retrieved 2008-04-11.
^Encyclopedia of Signaling Molecules. Cham: Springer International Publishing. 2018. doi:10.1007/978-3-319-67199-4. ISBN978-3-319-67198-7. 1-Structure and properties of 5-HT2B receptors: 1.1-Selective agonists: [...] - 5-Methoxytryptamine is also 25- and 400-fold selective over the 5-HT2A and 5-HT2C receptor sites, respectively.
^Zlotos DP (2012). "Recent progress in the development of agonists and antagonists for melatonin receptors". Curr Med Chem. 19 (21): 3532–3549. doi:10.2174/092986712801323153. PMID22680635.
^Zlotos DP (2014). "Development of Agonists and Antagonists for Melatonin Receptors". Melatonin and Melatonergic Drugs in Clinical Practice. New Delhi: Springer India. p. 97–116. doi:10.1007/978-81-322-0825-9_7. ISBN978-81-322-0824-2.
^Nakamura M, Fukushima H (April 1978). "Effects of reserpine, para-chlorophenylalanine, 5,6-dihydroxytryptamine and fludiazepam on the head twitches induced by 5-hydroxytryptamine or 5-methoxytryptamine in mice". J Pharm Pharmacol. 30 (4): 254–256. doi:10.1111/j.2042-7158.1978.tb13219.x. PMID24719.
^ abPrzegaliński E, Baran L, Palider W, Bigajska K (1978). "On the central antiserotonin activity of benzoctamine and opipramol". Pol J Pharmacol Pharm. 30 (6): 781–790. PMID582625.
^Baran L, Maj J, Rogóz Z, Skuza G (1979). "On the central antiserotonin action of trazodone". Pol J Pharmacol Pharm. 31 (1): 25–33. PMID482164.
^ abPrzegaliński E, Baran L, Palider W, Siwanowicz J (April 1979). "The central action of pizotifen". Psychopharmacology (Berl). 62 (3): 295–300. doi:10.1007/BF00431961. PMID111296.
^De Montigny C, Aghajanian GK (1977). "Preferential action of 5-methoxytryptamine and 5-methoxydimethyltryptamine on presynaptic serotonin receptors: A comparative iontophoretic study with LSD and serotonin". Neuropharmacology. 16 (12): 811–818. doi:10.1016/0028-3908(77)90142-3.
^Shulgin A (1997). TiHKAL: The Continuation(PDF). Transform Press. ISBN978-0-9630096-9-2. Retrieved 2 November 2024. One of its most broadly studied properties is that of protecting an experimental animal against the damage of being exposed to radiation. It was unexpectedly observed that our essential and favorite neurotransmitter serotonin was every bit as effective as a radioprotective agent. In efforts to make this natural compound more accessible to the damaged animal, it was studied as the unacetylated Omethyl ether. This simple compound, 5-methoxytryptamine (5-MeO-T, or Mexamine) has been mentioned under the recipe for 5-MeO-DMT in its possible effects in potentiating CNS-active drugs. But here it deserves to be highlighted for its protection against radiation. Two structural modification directions of 5-methoxytryptamine have been thoroughly explored. [...] A A 5-MeO-T anti-radiation, not a psychedelic ? [...] Removal of both methyl groups from the nitrogen gives 5- methoxytryptamine (5-MeO-T) which has been explored most extensively by Soviet researchers as a treatment for exposure to radiation; this aspect of its action is discussed and expanded upon in the commentary under Melatonin. It is also known by the trade name Mexamine and has been looked at as a potentiator of centrally active drugs.
^Boullin DJ, Green AR (1976). "5-Methoxytryptamine: stimulation of 5-HT receptors mediating the rat hyperactivity syndrome and blood platelet aggregation". Adv Biochem Psychopharmacol. 15: 127–140. PMID15408.
^Galzin AM, Langer SZ (July 1986). "Potentiation by deprenyl of the autoreceptor-mediated inhibition of [3H]-5-hydroxytryptamine release by 5-methoxytryptamine". Naunyn Schmiedebergs Arch Pharmacol. 333 (3): 330–333. doi:10.1007/BF00512949. PMID3093900.
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