5-Carboxamidotryptamine

5-Carboxamidotryptamine (5-CT) is a tryptamine derivative closely related to the neurotransmitter serotonin.

5-Carboxamidotryptamine
Identifiers
IUPAC name
  • 3-(2-Aminoethyl)-1H-indole-5-carboxamide
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H13N3O
Molar mass203.245 g·mol−1
3D model (JSmol)
SMILES
  • C1=CC2=C(C=C1C(=O)N)C(=CN2)CCN
InChI
  • InChI=1S/C11H13N3O/c12-4-3-8-6-14-10-2-1-7(11(13)15)5-9(8)10/h1-2,5-6,14H,3-4,12H2,(H2,13,15) Y
  • Key:WKZLNEWVIAGNAW-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

5-CT acts as a non-selective, high-affinity full agonist at the 5-HT1A, 5-HT1B, 5-HT1D, 5-HT5A, and 5-HT7 receptors, as well as at the 5-HT2, 5-HT3, 5-HT6 receptors with lower affinity.[1][2][3] It has negligible affinity for the 5-HT1E and 5-HT1F receptors.[4] 5-CT binds most strongly to the 5-HT1A receptor and it was once thought to be selective for this site.[5][6] Recently, a close derivative of 5-CT, AH-494 has been shown to function as an agonist of 5-HT7, although being more selective over 5-HT1A.[7] Structural study indicated residue Ser5x43 might play critical roles in the selectivity of 5-CT across the serotonin receptor family.[8]

See also

References
  1. Yamada J, Sugimoto Y, Noma T, Yoshikawa T (October 1998). "Effects of the non-selective 5-HT receptor agonist, 5-carboxamidotryptamine, on plasma glucose levels in rats". European Journal of Pharmacology. 359 (1): 81–86. doi:10.1016/S0014-2999(98)00617-7. PMID 9831297.
  2. Wright CE, Angus JA (April 1989). "5-carboxamidotryptamine elicits 5-HT2 and 5-HT3 receptor-mediated cardiovascular responses in the conscious rabbit: evidence for 5-HT release from platelets". Journal of Cardiovascular Pharmacology. 13 (4): 557–564. doi:10.1097/00005344-198913040-00007. PMID 2470992.
  3. Glennon RA, Dukat M, Westkaemper RB (2000-01-01). "Serotonin Receptor Subtypes and Ligands". American College of Neurophyscopharmacology. Archived from the original on 21 April 2008. Retrieved 2008-04-11.
  4. Stanton JA, Middlemiss DN, Beer MS (February 1996). "Autoradiographic localization of 5-CT-insensitive 5-HT1-like recognition sites in guinea pig and rat brain". Neuropharmacology. 35 (2): 223–229. doi:10.1016/0028-3908(95)00178-6. PMID 8734492. S2CID 27188133.
  5. Thomas DR, Middlemiss DN, Taylor SG, Nelson P, Brown AM (September 1999). "5-CT stimulation of adenylyl cyclase activity in guinea-pig hippocampus: evidence for involvement of 5-HT7 and 5-HT1A receptors". British Journal of Pharmacology. 128 (1): 158–164. doi:10.1038/sj.bjp.0702759. PMC 1571602. PMID 10498847.
  6. Saxena PR, Lawang A (October 1985). "A comparison of cardiovascular and smooth muscle effects of 5-hydroxytryptamine and 5-carboxamidotryptamine, a selective agonist of 5-HT1 receptors". Archives Internationales de Pharmacodynamie et de Therapie. 277 (2): 235–252. PMID 2933009.
  7. Latacz G, Hogendorf AS, Hogendorf A, Lubelska A, Wierońska JM, Woźniak M, et al. (November 2018). "Search for a 5-CT alternative. In vitro and in vivo evaluation of novel pharmacological tools: 3-(1-alkyl-1H-imidazol-5-yl)-1H-indole-5-carboxamides, low-basicity 5-HT7 receptor agonists". MedChemComm. 9 (11): 1882–1890. doi:10.1039/c8md00313k. PMC 6256855. PMID 30568756.
  8. Zhang S, Chen H, Zhang C, Yang Y, Popov P, Liu J, et al. (July 2022). "Inactive and active state structures template selective tools for the human 5-HT5A receptor". Nature Structural & Molecular Biology. 29 (7): 677–687. doi:10.1038/s41594-022-00796-6. PMC 9299520. PMID 35835867.


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