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5-Fluoro-AMT

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5-Fluoro-AMT
Identifiers
  • 1-(5-fluoro-1H-indol-3-yl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H13FN2
Molar mass192.233 g/mol g·mol−1
3D model (JSmol)
  • 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 checkY
  • Key:CTGFDWBZMCPVED-UHFFFAOYSA-N checkY
 ☒NcheckY (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,[1] a 5-HT2A receptor agonist,[2] and a potent and specific MAO-A inhibitor.[3][4] It produces a strong head-twitch response in mice, and this effect is known to correlate with psychedelic effects in humans,[5][6] 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. ^ a b Banks, M. L.; Bauer, C. T.; Blough, B. E.; Rothman, R. B.; Partilla, J. S.; Baumann, M. H.; Negus, S. S. (2014). "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): 274–84. doi:10.1037/a0036595. PMC 4067459. PMID 24796848.
  2. ^ Chairungsrilerd, N; Furukawa, K; Tadano, T; Kisara, K; Ohizumi, Y (Mar 1998). "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): 855–62. doi:10.1038/sj.bjp.0701695. PMC 1565246. PMID 9535013.
  3. ^ Kinemuchi, H; Arai, Y (Oct 1986). "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.
  4. ^ Kim, SK; Toyoshima, Y; Arai, Y; Kinemuchi, H; Tadano, T; Oyama, K; Satoh, N; Kisara, K (Apr 1991). "Inhibition of monoamine oxidase by two substrate-analogues, with different preferences for 5-hydroxytryptamine neurons". Neuropharmacology. 30 (4): 329–35. doi:10.1016/0028-3908(91)90057-i. PMID 1852266.
  5. ^ Corne, SJ; Pickering, RW (1967). "A possible correlation between drug induced hallucinations in man and a behavioral response in mice". Psychopharmacologia. 11 (1): 65–78. doi:10.1007/bf00401509. PMID 5302272.
  6. ^ Yamamoto, T; Ueki, S (Jan 1981). "The role of central serotonergic mechanisms on head-twitch and backward locomotion induced by halluinogenic drugs". Pharmacology, Biochemistry and Behaviour. 1981 (14): 89–95. doi:10.1016/0091-3057(81)90108-8. PMID 6258178.

Further reading


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