7-Fluorotryptamine

7-Fluorotryptamine
Clinical data
Other names7-F-T; 7-Fluoro-T; 7-FT
Drug classSerotonin receptor modulator; GPRC5A agonist
ATC code
  • None
Identifiers
  • 2-(7-fluoro-1H-indol-3-yl)ethanamine
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.197.219
Chemical and physical data
FormulaC10H11FN2
Molar mass178.210 g·mol−1
3D model (JSmol)
  • C1=CC2=C(C(=C1)F)NC=C2CCN
  • InChI=1S/C10H11FN2/c11-9-3-1-2-8-7(4-5-12)6-13-10(8)9/h1-3,6,13H,4-5,12H2
  • Key:QRAWNNQNLQPNIZ-UHFFFAOYSA-N

7-Fluorotryptamine (7-FT) is a serotonin receptor modulator and weak GPRC5A agonist of the tryptamine family.[1][2] It is the 7-fluoro derivative of tryptamine.[2] The drug is a low-potency agonist of the orphan receptor GPRC5A, with an EC50Tooltip half-maximal effective concentration of 7,200 nM.[1][2][3] In addition to its GPRC5A agonism, 7-fluorotryptamine interacts with other receptors, such as the serotonin 5-HT4 receptor.[2] Derivatives of 7-fluorotryptamine have been described.[4] 7-Fluorotryptamine was first described in the scientific literature by 1979.[5] Its GPRC5A agonism was first described in 2023.[2]

See also

References

  1. ^ a b Huang WC, Lin WT, Hung MS, Lee JC, Tung CW (January 2024). "Decrypting orphan GPCR drug discovery via multitask learning". Journal of Cheminformatics. 16 (1) 10. doi:10.1186/s13321-024-00806-3. PMC 10804799. PMID 38263092. During the review process of the manuscript, two agonistic ligands of 7-fluorotryptamine and tryptamine were reported for the orphan GPRC5A [43]. With a Ts of 6.2%, a good MSE of 1.46 was obtained using the MTL-AG-ATG-FS model. Detailed prediction is listed in Additional file 1: Table S5. For the promising agonist of 7-fluorotryptamine, its predicted EC50 is 2.4 μM, which is close to the experimental value of 7.2 μM [43]. This provides a successful example for predicting ligands of an orphan receptor.
  2. ^ a b c d e Zhao X, Stein KR, Chen V, Griffin ME, Lairson LL, Hang HC (October 2023). "Chemoproteomics reveals microbiota-derived aromatic monoamine agonists for GPRC5A". Nature Chemical Biology. 19 (10): 1205–1214. doi:10.1038/s41589-023-01328-z. PMID 37248411.
  3. ^ Hamrick SK, Thompson M, Drake LY, Venkatachalem S, Pabelick CM, Prakash YS (1 May 2025). "Class C GPRC5A in Human Airway Smooth Muscle". American Journal of Respiratory and Critical Care Medicine. 211 (Supplement_1) A3084. doi:10.1164/ajrccm.2025.211.Abstracts.A3084. ISSN 1073-449X.
  4. ^ Kawase M, Sinhababu AK, McGhee EM, Milby T, Borchardt RT (August 1990). "Synthesis and biological evaluation of 4-fluoro-, 7-fluoro-, and 4,7-difluoro-5,6-dihydroxytryptamines". Journal of Medicinal Chemistry. 33 (8): 2204–2211. doi:10.1021/jm00170a026. PMID 2100997.
  5. ^ Treimer JF, Zenk MH (November 1979). "Purification and properties of strictosidine synthase, the key enzyme in indole alkaloid formation". European Journal of Biochemistry. 101 (1): 225–233. Bibcode:1979EJBio.101..225T. doi:10.1111/j.1432-1033.1979.tb04235.x. PMID 510306.
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