5-Fluorotryptamine

5-FT is known to have affinity for the serotonin 5-HT_1A and 5-HT_2A receptors, with K_i values of 18 nM and 6.0–3,908 nM, respectively.^[3][4][5] It is a full agonist of the serotonin 5-HT_2A receptor, with an EC₅₀Tooltip half-maximal effective concentration of 2.64 to 58 nM and an E_maxTooltip half-maximal effective concentration of 110%.^[2][4] The drug is also an agonist of the serotonin 5-HT_1A receptor, with an EC₅₀ of 129 nM.^[4] 5-HT shows high affinity for the serotonin 5-HT_2B and 5-HT_2C receptors as well (K_i = 5.7 nM and 3.72 nM, respectively).^[5] In addition to its serotonin receptor agonism, 5-FT is a serotonin–dopamine releasing agent (SDRA), with EC₅₀ values for induction of monoamine release of 10.1 nM for serotonin, 82.3 nM for dopamine, and 464 nM for norepinephrine.^[2] The drug is also a weak monoamine oxidase inhibitor (MAOI), with IC₅₀Tooltip half-maximal inhibitory concentration values of 13,200 nM for monoamine oxidase A (MAO-A) and 52,500 nM for monoamine oxidase B (MAO-B).^[1][6]

Despite its serotonin 5-HT_2A receptor agonism, 5-FT failed to induce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, suggesting that it may not have hallucinogenic effects in humans.^[1][6]

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.^{[7][8][9][10][11][12][13]} However, given intravenously at sufficiently high doses, tryptamine is still known to be able to produce weak and short-lived psychoactive effects in humans.^{[14][8][2][13]}

5-FT was first described in the scientific literature by 1983.^[15]

• Substituted tryptamine
• 6-Fluorotryptamine (6-FT)
• 7-Chlorotryptamine (7-CT)
• 5-Fluoro-AMT
• 5-Fluoro-AET
• 5-Fluoro-DMT
• 5-Fluoro-DET
• Bretisilocin (5-fluoro-MET)
• 5-Fluoro-EPT
• 5-Methyltryptamine
• 5-Methoxytryptamine