5-Fluoro-AET

5-Fluoro-AET
Clinical data
Other names5-Fluoro-α-ethyltryptamine; 5-F-AET; 5F-AET; 5-Fluoro-αET; 5-F-αET; 5F-αET; PAL-545
Drug classSerotonin–norepinephrine–dopamine releasing agent; Serotonin receptor agonist; Entactogen
Identifiers
IUPAC name
  • 1-(5-fluoro-1H-indol-3-yl)butan-2-amine
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC12H15FN2
Molar mass206.264 g·mol−1
3D model (JSmol)
SMILES
  • CCC(CC1=CNC2=C1C=C(C=C2)F)N
InChI
  • InChI=1S/C12H15FN2/c1-2-10(14)5-8-7-15-12-4-3-9(13)6-11(8)12/h3-4,6-7,10,15H,2,5,14H2,1H3
  • Key:QGUZSMSUGSSPNJ-UHFFFAOYSA-N

5-Fluoro-AET, also known as 5-fluoro-α-ethyltryptamine or by the code name PAL-545, is a substituted tryptamine derivative which acts as a serotonin–dopamine releasing agent (SDRA) and as an agonist of the serotonin 5-HT2A receptor.[1]

Its EC50Tooltip half-maximal effective concentration values for monoamine release are 36.6 nM for serotonin, 5,334 nM for norepinephrine, and 150 nM for dopamine in rat brain synaptosomes.[1] Its EC50 at the serotonin 5-HT2A receptor is 246 nM and its EmaxTooltip maximal efficacy at the receptor is 87%.[1]

Several close analogues of 5-fluoro-αET, including 5-fluoro-αMT and 5-chloro-αMT, are known to be potent monoamine oxidase inhibitors (MAOIs), specifically of monoamine oxidase A (MAO-A).[2] However, α-ethyltryptamine (αET) is a very weak MAOI.[3][4] 5-Fluoro-αET has also more recently been assessed, and in contrast to αET, but similarly to drugs like 5-fluoro-αET, was found to be a potent MAOI, with an IC50Tooltip half-maximal inhibitory concentration of 2,480 nM.[5] Potent monoamine oxidase inhibition by monoamine releasing agents (MRAs) has been associated with dangerous and sometimes fatal toxicity in humans.[2]

  1. ^ a b c Blough BE, Landavazo A, Partilla JS, Decker AM, Page KM, Baumann MH, Rothman RB (October 2014). "Alpha-ethyltryptamines as dual dopamine-serotonin releasers". Bioorganic & Medicinal Chemistry Letters. 24 (19): 4754–4758. doi:10.1016/j.bmcl.2014.07.062. PMC 4211607. PMID 25193229.
  2. ^ a b Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK (2019). "Amphetamine Derivatives as Monoamine Oxidase Inhibitors". Front Pharmacol. 10 1590. doi:10.3389/fphar.2019.01590. PMC 6989591. PMID 32038257. Several close analogues of 5-chloro-αET, such as 5-chloro-αMT and 5-fluoro-αMT, are known to be potent monoamine oxidase inhibitors (MAOIs).
  3. ^ Glennon RA, Dukat MG (December 2023). "α-Ethyltryptamine: A Ratiocinatory Review of a Forgotten Antidepressant". ACS Pharmacology & Translational Science. 6 (12): 1780–1789. doi:10.1021/acsptsci.3c00139. PMC 10714429. PMID 38093842.
  4. ^ Ask AL, Fagervall I, Ross SB (September 1983). "Selective inhibition of monoamine oxidase in monoaminergic neurons in the rat brain". Naunyn-Schmiedeberg's Archives of Pharmacology. 324 (2): 79–87. doi:10.1007/BF00497011. PMID 6646243.
  5. ^ WO 2022061242, Matthew Baggott, "Advantageous tryptamine compositions for mental disorders or enhancement", published 2023 March 24, assigned to Tactogen 
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