5-Fluoro-AMT explained

5-Fluoro-α-methyltryptamine (5-Fluoro-αMT, 5F-AMT), also known as PAL-212^[1] or PAL-544,^{[2] [3]} is a putative stimulant, entactogen, and psychedelic tryptamine derivative related to α-methyltryptamine (αMT).

It has been found to act as a fairly balanced serotonin-norepinephrine-dopamine releasing agent (SNDRA), as a serotonin 5-HT_2A receptor agonist,^[4] and as a potent and specific MAO-A inhibitor.^{[5] [6] [7] [8] [9]} Its values in terms of monoamine release are 14 to 19nM for serotonin, 78 to 126nM for norepinephrine, and 32 to 37nM for dopamine. Its at the serotonin 5-HT_2A receptor is 8.47nM and its at the receptor is 107%.^[10]

The of 5-fluoro-AMT for MAO-A is 180 to 450nM.^{[11] [12]} This is similar to the potency of para-methoxyamphetamine (PMA) and 4-methylthioamphetamine (4-MTA).

The potent serotonin 5-HT_2A receptor agonism of 5-fluoro-αMT suggests that it could be an active psychedelic in humans, although it is not known to have been tested in humans and could be dangerous due to its strong inhibition of MAO-A. Accordingly, 5-fluoro-αMT induces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.^{[13] [14] [15]}

See also

• 5-Chloro-αMT
• 5-Fluoro-AET
• 5-Fluoro-DMT
• 6-Fluoro-AMT
• 7-Chloro-AMT
• 7-Methyl-αET
• Flucindole
• 5-API (PAL-571)

Further reading

• Nakagawasai O, Arai Y, Satoh SE, Satoh N, Neda M, Hozumi M, Oka R, Hiraga H, Tadano T . 6 . Monoamine oxidase and head-twitch response in mice. Mechanisms of alpha-methylated substrate derivatives . Neurotoxicology . 25 . 1–2 . 223–32 . January 2004 . 14697897 . 10.1016/S0161-813X(03)00101-3 . 2004NeuTx..25..223N .

Notes and References

1. Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB . Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes . Psychopharmacology (Berl) . 231 . 21 . 4135–4144 . October 2014 . 24800892 . 4194234 . 10.1007/s00213-014-3557-7 .
2. Banks ML, Bauer CT, Blough BE, Rothman RB, Partilla JS, Baumann MH, Negus SS . Abuse-related effects of dual dopamine/serotonin releasers with varying potency to release norepinephrine in male rats and rhesus monkeys . Experimental and Clinical Psychopharmacology . 22 . 3 . 274–284 . June 2014 . 24796848 . 4067459 . 10.1037/a0036595 .
3. Web site: 5-Fluoro-AMT . Isomer Design . 11 November 2024 . 7 December 2024.
4. Chairungsrilerd N, Furukawa K, Tadano T, Kisara K, Ohizumi Y . Effect of gamma-mangostin through the inhibition of 5-hydroxy-tryptamine2A receptors in 5-fluoro-alpha-methyltryptamine-induced head-twitch responses of mice . British Journal of Pharmacology . 123 . 5 . 855–862 . March 1998 . 9535013 . 1565246 . 10.1038/sj.bjp.0701695 .
5. Wagmann L, Brandt SD, Kavanagh PV, Maurer HH, Meyer MR . In vitro monoamine oxidase inhibition potential of alpha-methyltryptamine analog new psychoactive substances for assessing possible toxic risks . Toxicol Lett . 272 . 84–93 . April 2017 . 28302559 . 10.1016/j.toxlet.2017.03.007 .
6. Kinemuchi H, Arai Y . Selective inhibition of monoamine oxidase A and B by two substrate-analogues, 5-fluoro-alpha-methyltryptamine and p-chloro-beta-methylphenethylamine . Research Communications in Chemical Pathology and Pharmacology . 54 . 1 . 125–8 . October 1986 . 3797802 . 10.1016/0028-3908(91)90057-i . 34761939 .
7. Kim SK, Toyoshima Y, Arai Y, Kinemuchi H, Tadano T, Oyama K, Satoh N, Kisara K . 6 . Inhibition of monoamine oxidase by two substrate-analogues, with different preferences for 5-hydroxytryptamine neurons . Neuropharmacology . 30 . 4 . 329–35 . April 1991 . 1852266 . 10.1016/0028-3908(91)90057-i . 34761939 .
8. Corne SJ, Pickering RW . A possible correlation between drug-induced hallucinations in man and a behavioural response in mice . Psychopharmacologia . 11 . 1 . 65–78 . 1967 . 5302272 . 10.1007/bf00401509 . 3148623 .
9. Yamamoto T, Ueki S . The role of central serotonergic mechanisms on head-twitch and backward locomotion induced by hallucinogenic drugs . Pharmacology, Biochemistry, and Behavior . 14 . 1 . 89–95 . January 1981 . 6258178 . 10.1016/0091-3057(81)90108-8 . 45561708 .
10. Blough BE, Landavazo A, Partilla JS, Decker AM, Page KM, Baumann MH, Rothman RB . Alpha-ethyltryptamines as dual dopamine-serotonin releasers . Bioorg Med Chem Lett . 24 . 19 . 4754–4758 . October 2014 . 25193229 . 4211607 . 10.1016/j.bmcl.2014.07.062 .
11. Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK . Amphetamine Derivatives as Monoamine Oxidase Inhibitors . Front Pharmacol . 10 . 1590 . 2019 . 32038257 . 6989591 . 10.3389/fphar.2019.01590 . free .
12. Nakagawasai O, Arai Y, Satoh SE, Satoh N, Neda M, Hozumi M, Oka R, Hiraga H, Tadano T . Monoamine oxidase and head-twitch response in mice. Mechanisms of alpha-methylated substrate derivatives . Neurotoxicology . 25 . 1–2 . 223–232 . January 2004 . 14697897 . 10.1016/S0161-813X(03)00101-3 . 2004NeuTx..25..223N .
13. Halberstadt AL, Geyer MA . Effect of Hallucinogens on Unconditioned Behavior . Curr Top Behav Neurosci . Current Topics in Behavioral Neurosciences . 36 . 159–199 . 2018 . 28224459 . 5787039 . 10.1007/7854_2016_466 . 978-3-662-55878-2 .
14. Nakagawasai O, Arai Y, Satoh SE, Satoh N, Neda M, Hozumi M, Oka R, Hiraga H, Tadano T . Monoamine oxidase and head-twitch response in mice. Mechanisms of alpha-methylated substrate derivatives . Neurotoxicology . 25 . 1–2 . 223–232 . January 2004 . 14697897 . 10.1016/S0161-813X(03)00101-3 . 2004NeuTx..25..223N .
15. Tadano T, Neda M, Hozumi M, Yonezawa A, Arai Y, Fujita T, Kinemuchi H, Kisara K . alpha-Methylated tryptamine derivatives induce a 5-HT receptor-mediated head-twitch response in mice . Neuropharmacology . 34 . 2 . 229–234 . February 1995 . 7617148 . 10.1016/0028-3908(94)00119-d .