6-Methoxytryptamine
Pharmaceutical compound
From Wikipedia, the free encyclopedia
6-Methoxytryptamine (6-MeO-T; developmental code name PAL-263) is a monoamine releasing agent and serotonin receptor modulator of the tryptamine family.[1] It is a positional isomer of 5-methoxytryptamine.[1]
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| Other names | 6-Methoxy-T; 6-MeO-T; PAL-263; PAL263 |
| Drug class | Monoamine releasing agent; Serotonin–norepinephrine–dopamine releasing agent; Serotonin receptor modulator |
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| ECHA InfoCard | 100.020.708 |
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| Formula | C11H14N2O |
| Molar mass | 190.246 g·mol−1 |
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Pharmacology
6-Methoxytryptamine is a potent serotonin–norepinephrine–dopamine releasing agent (SNDRA), with EC50 values for monoamine release induction of 53.8 nM for serotonin, 113 nM for dopamine, and 465 nM for norepinephrine in rat brain synaptosomes.[1] It is also a full agonist of the serotonin 5-HT2A receptor, but with very low potency; its EC50 and Emax at this receptor were 2,443 nM and 111%, respectively.[1] In a series of tryptamine derivatives, 6-methoxytryptamine was the least potent serotonin 5-HT2A receptor agonist, while 5-methoxytryptamine was the most potent serotonin 5-HT2A receptor agonist, with 5-methoxytryptamine showing approximately 4,857-fold higher potency in terms of serotonin 5-HT2A receptor agonism than 6-methoxytryptamine.[1] Conversely, whereas 6-methoxytryptamine was a potent monoamine releasing agent, 5-methoxytryptamine showed very low potency in this regard.[1]
History
6-Methoxytryptamine was first described in the scientific literature by the 1950s.[2]
Derivatives
Certain β-carbolines and harmala alkaloids, such as harmine, harmaline, and tetrahydroharmine, are notable in being naturally occurring cyclized tryptamine derivatives of 6-methoxytryptamine.[3][4] The same is true of certain iboga alkaloids, such as tabernanthine and ibogaline.[5][6][7][8] Tabernanthalog (DLX-007) is a synthetic simplified ibogalog analogue of tabernanthine that is under development for use as a potential pharmaceutical drug in the treatment of neuropsychiatric disorders.[9][10]