6-Methoxytryptamine
6-Methoxytryptamine is a monoamine releasing agent and serotonin receptor modulator of the tryptamine family. It is a positional isomer of 5-methoxytryptamine.Pharmacology
6-Methoxytryptamine is a potent serotonin–norepinephrine–dopamine releasing agent, with values for monoamine release induction of 53.8nM for serotonin, 113nM for dopamine, and 465nM for norepinephrine in rat brain synaptosomes. It is also a full agonist of the serotonin 5-HT2A receptor, but with very low potency; its and at this receptor were 2,443nM and 111%, respectively. 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. Conversely, whereas 6-methoxytryptamine was a potent monoamine releasing agent, 5-methoxytryptamine showed very low potency in this regard.History
6-Methoxytryptamine was first described in the scientific literature by the 1950s.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. The same is true of certain iboga alkaloids, such as tabernanthine and ibogaline. Tabernanthalog 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.