5-Carboxamidotryptamine

5-Carboxamidotryptamine
Identifiers
  • 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)
  • C1=CC2=C(C=C1C(=O)N)C(=CN2)CCN
  • 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) checkY
  • Key:WKZLNEWVIAGNAW-UHFFFAOYSA-N checkY
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5-Carboxamidotryptamine (5-CT) is a tryptamine derivative closely related to the neurotransmitter serotonin.

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 an agonist of 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]

  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.