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 N
PubChem CID	1809
IUPHAR/BPS	4
ChemSpider	1743 Y
UNII	91H76044O0
ChEBI	CHEBI:48292 Y
ChEMBL	ChEMBL18840 Y
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) 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-HT_1A, 5-HT_1B, 5-HT_1D, 5-HT_5A, and 5-HT₇ receptors, as well as an agonist of the 5-HT₂, 5-HT₃, 5-HT₆ receptors with lower affinity.^[1][2][3][4] It has negligible affinity for the 5-HT_1E and 5-HT_1F receptors.^[5] 5-CT binds most strongly to the 5-HT_1A receptor and it was once thought to be selective for this site.^[6][7]

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.^[8] Structural study indicated residue Ser5x43 might play critical roles in the selectivity of 5-CT across the serotonin receptor family.^[9]

See also

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