5-Carboxamidotryptamine

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 ;
ChEBI	CHEBI:48292 ;
ChEMBL	ChEMBL18840 ;
Chemical and physical data
Formula	C11H13N3O
Molar mass	203.240 g/mol 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-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-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 strongest to the 5-HT_1A receptor and it was once thought to be selective for this site.[5][6]

References

Yamada J, Sugimoto Y, Noma T, Yoshikawa T (1998). "Effects of the non-selective 5-HT receptor agonist, 5-carboxamidotryptamine, on plasma glucose levels in rats". Eur J Pharmacol. 359 (1): 81–86. doi:10.1016/S0014-2999(98)00617-7. PMID 9831297.
Wright, CE; Angus, JA (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. PMID 2470992.
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.
Stanton JA, Middlemiss DN, Beer MS (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.
Thomas, DR; Middlemiss, DN; Taylor, SG; Nelson, P; Brown, AM (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.
Saxena, PR; Lawang, A (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 Thérapie. 277 (2): 235–52. PMID 2933009.

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[pmid9831297-1] Yamada J, Sugimoto Y, Noma T, Yoshikawa T (1998). "Effects of the non-selective 5-HT receptor agonist, 5-carboxamidotryptamine, on plasma glucose levels in rats". Eur J Pharmacol. 359 (1): 81–86. doi:10.1016/S0014-2999(98)00617-7. PMID 9831297.

[2] Wright, CE; Angus, JA (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. PMID 2470992.

[urlSerotonin_Receptor_Subtypes_and_Ligands-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.

[pmid8734492-4] Stanton JA, Middlemiss DN, Beer MS (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.

[5] Thomas, DR; Middlemiss, DN; Taylor, SG; Nelson, P; Brown, AM (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 (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 Thérapie. 277 (2): 235–52. PMID 2933009.

5-Carboxamidotryptamine

See also

References