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	74885-09-9
PubChem CID	1809
IUPHAR/BPS	4
ChemSpider	1743
UNII	91H76044O0
ChEBI	CHEBI:48292
ChEMBL	ChEMBL18840
CompTox Dashboard (EPA)	DTXSID60996379
Chemical and physical data
Formula	C11H13N3O
Molar mass	203.245 g·mol^−1
3D model (JSmol)	Interactive image
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) Key:WKZLNEWVIAGNAW-UHFFFAOYSA-N
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5-CT acts as a non-selective, high-affinity full agonist at the 5-HT_1A, 5-HT_1B, 5-HT_1D, 5-HT_5A, 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-HT_1E and 5-HT_1F receptors.[4] 5-CT binds most strongly to the 5-HT_1A 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]

See also

• 2-Methyl-5-hydroxytryptamine
• 5-Benzyloxytryptamine
• 5-Methoxytryptamine
• α-Methyl-5-hydroxytryptamine
• Frovatriptan
• AH-494
• Acetryptine
• Sumatriptan

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): 81–6. 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): 557–64. 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): 223–9. 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): 158–64. 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): 235–52. PMID 2933009.
7. Latacz G, Hogendorf AS, Hogendorf A, Lubelska A, Wierońska JM, Woźniak M, et al. (November 2018). "7 receptor agonists". MedChemComm. 9 (11): 1882–1890. doi:10.1039/c8md00313k. PMC 6256855. PMID 30568756.