5-Fluoro-AMT

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5-Fluoro-αMT, also known as 5-fluoro-α-methyltryptamine (5F-AMT) or as PAL-212[2][3] or PAL-544,[4][5] is a monoaminergic drug of the tryptamine and α-alkyltryptamine families related to α-methyltryptamine (αMT).[2][3][4]

The drug is known to act as a serotonin receptor agonist,[2][3] monoamine releasing agent,[2][3][4] and potent monoamine oxidase inhibitor.[6][7] It produces psychedelic- and stimulant-like effects in animals.[8][7][9][10] 5-Fluoro-AMT is also known to be psychoactive in humans, though its effects have not been well-described.[1][11]

5-Fluoro-AMT was first described in the scientific literature by 1963.[10] There has been interest in 5-fluoro-AMT as a possible treatment for cocaine dependence.[4]

Use and effects

5-Fluoro-AMT has been said to be psychoactive in humans at a dose of 25Script error: No such module "String".mg orally, although the qualitative nature of these effects has not been well-described.[1][11] Preclinical studies suggest that 5-fluoro-αMT may be a psychedelic, stimulant, and/or entactogen in humans.[2][3][4][8][7][9][10] However, 5-fluoro-AMT may be dangerous in humans due to its concomitant potent monoamine oxidase inhibition.[6][12]

William Leonard Pickard has described his experiences with 5-fluoro-AMT, which he had synthesized along with 6-fluoro-AMT, in personal interviews.[11] According to Pickard, 5-fluoro-AMT had a duration of at minimum 9Script error: No such module "String".hours and varied in length significantly.[11] The dosage was 25Script error: No such module "String".mg and above.[11] Pickard has said that 5-fluoro-AMT was not a "warm drug" but that he remained favorable to it.[11] Its effects included time dilation among others.[11] He said that it gave him the worst post-trip headaches he'd experienced from any psychedelic and they lasted up to 24Script error: No such module "String".hours.[11]

Pickard has said that 5-fluoro-AMT is less potent and long-lasting than 6-fluoro-AMT.[11] The related drug AMT was one of Pickard's favorite psychedelics, and he said that he took it more than 50Script error: No such module "String".times and experienced no negative side effects with it.[11]

Pharmacology

5-Fluoro-AMT has been found to act as a fairly balanced serotonin-norepinephrine-dopamine releasing agent (SNDRA),[4][2] as a serotonin 5-HT2A receptor agonist,[2][13] and as a potent and specific MAO-A inhibitor.[12][14][15][16][17] Its EC50Tooltip half-maximal effective concentration values in terms of monoamine release are 14 to 19Script error: No such module "String".nM for serotonin, 78 to 126Script error: No such module "String".nM for norepinephrine, and 32 to 37Script error: No such module "String".nM for dopamine in rat brain synaptosomes.[4][2][3] The drug's EC50 at the serotonin 5-HT2A receptor is 8.47Script error: No such module "String".nM and its EmaxTooltip maximal efficacy at the receptor is 107%.[3] The IC50Tooltip half-maximal inhibitory concentration of 5-fluoro-AMT for MAO-A is 180 to 450Script error: No such module "String".nM.[6][7][12] This is similar to the potency of αMT, para-methoxyamphetamine (PMA), and 4-methylthioamphetamine (4-MTA).[6]

5-Fluoro-αMT induces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.[8][7][9] It is also known to reverse reserpine-induced behavioral depression, suggesting that it has antidepressant- or stimulant-like effects as well.[10] 5-Fluoro-AMT does not substitute for cocaine in drug discrimination tests but did substitute for cocaine in monkeys.[4] It does not facilitate intracranial self-stimulation (ICSS) in rodents.[4]

Chemistry

Analogues of 5-fluoro-AMT include 5-fluorotryptamine, 5-fluoro-DMT, 5-fluoro-AET, and BK-5F-NM-AMT, as well as 5-chloro-αMT, 6-fluoro-AMT, 7-chloro-AMT, 7-methyl-αET, 5-API (PAL-571), and flucindole, among others. BK-5F-NM-AMT, the N-methyl and β-keto derivative of 5-fluoro-AMT, is a serotonin–dopamine releasing agent (SDRA) analogously to 5-fluoro-AMT.[18] In contrast to 5-fluoro-AMT and many other tryptamines however, BK-5F-NM-AMT is inactive as an agonist of serotonin receptors including the 5-HT1, 5-HT2, and 5-HT3 receptors and is inactive as a monoamine oxidase inhibitor (MAOI).[18]

History

5-Fluoro-AMT was first described in the scientific literature, by Asher Kalir and Stephen Szara, by 1963, and was described as showing antidepressant- or stimulant-like effects in rodents.[10] It was first tried in humans by 1984.[1] The drug's psychedelic-like effects in animals were described by 1995,[9] 5-Fluoro-AMT's monoamine release and serotonin receptor agonism were shown by 2014, along with support for it having stimulant-like effects in monkeys.[2][3][4] The drug was investigated as a possible candidate for treatment of cocaine dependence and these findings were published in 2014.[4]

References

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  18. ↑ a b <templatestyles src="Citation/styles.css"/>Template:Citation/make link, Baggott M, "Advantageous tryptamine compositions for mental disorders or enhancement", published Script error: No such module "auto date formatter"., assigned to Tactogen Script error: No such module "Check for unknown parameters".

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External links

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