5-Fluoro-AMT

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5-Fluoro-AMT
5-fluoro-alpha-methyltryptamine.svg
5-Fluoro-α-methyltryptamine.png
Systematic (IUPAC) name
1-(5-fluoro-1H-indol-3-yl)propan-2-amine
Identifiers
CAS Number 712-08-3 N
PubChem CID: 12834
ChemSpider 12304 YesY
ChEMBL CHEMBL96816 YesY
Chemical data
Formula C11H13FN2
Molecular mass 192.233 g/mol
  • Fc1cc2c(cc1)ncc2CC(N)C
  • InChI=1S/C11H13FN2/c1-7(13)4-8-6-14-11-3-2-9(12)5-10(8)11/h2-3,5-7,14H,4,13H2,1H3 YesY
  • Key:CTGFDWBZMCPVED-UHFFFAOYSA-N YesY
 NYesY (what is this?)  (verify)

5-Fluoro-α-methyltryptamine (5-Fluoro-αMT), also known as PAL-544,[1] is a putative stimulant, entactogen, and psychedelic tryptamine derivative related to α-methyltryptamine (αMT). It has been found to act as a well-balanced serotonin-norepinephrine-dopamine releasing agent,[2] a 5-HT2A receptor agonist,[3] and a potent and specific MAO-A inhibitor.[4][5] It produces a strong head-twitch response in mice, and this effect is known to correlate with psychedelic effects in humans,[6][7] which suggests that 5-fluoro-αMT 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.

See also

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ 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. 1998 Mar;123(5):855-62.
  4. ↑ 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. 1986 Oct;54(1):125-8.
  5. ↑ Kim SK, Toyoshima Y, Arai Y, Kinemuchi H, Tadano T, Oyama K, Satoh N, Kisara K. Inhibition of monoamine oxidase by two substrate-analogues, with different preferences for 5-hydroxytryptamine neurons. Neuropharmacology. 1991 Apr;30(4):329-35.
  6. ↑ Corne SJ, Pickering RW. A possible correlation between drug induced hallucinations in man and a behavioral response in mice. Psychopharmacologia 1967, 11, 65-78.
  7. ↑ Yamamoto T, Ueki S. The role of central serotonergic mechanisms on head-twitch and backward locomotion induced by halluinogenic drugs. Pharmacology, Biochemistry and Behaviour. 1981, 14, 89-95.


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