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
Molar mass 192.233 g/mol
 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,[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[edit]

References[edit]

  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. PMID 24796848. 
  2. ^ 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. PMID 9535013 PMC 1565246
  3. ^ 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.
  4. ^ 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. PMID 3797802
  5. ^ Corne SJ, Pickering RW. A possible correlation between drug induced hallucinations in man and a behavioral response in mice. Psychopharmacologia 1967, 11, 65-78. PMID 5302272
  6. ^ 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. PMID 6258178

Further reading[edit]

  • Nakagawasai O et al. Monoamine oxidase and head-twitch response in mice. Mechanisms of alpha-methylated substrate derivatives. Neurotoxicology. 2004 Jan;25(1-2):223-32. PMID 14697897