5-Carboxamidotryptamine

{{Short description|Chemical compound}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477224175

| IUPAC_name = 3-(2-Aminoethyl)-1H-indole-5-carboxamide

| image = 5-Carboxamidotryptamine.svg

| width = 180

| tradename =

| legal_status =

| routes_of_administration =

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| elimination_half-life =

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| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 74885-09-9

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 91H76044O0

| PubChem = 1809

| IUPHAR_ligand = 4

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

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| ChemSpiderID = 1743

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 48292

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 18840

| C=11 | H=13 | N=3 | O=1

| smiles = C1=CC2=C(C=C1C(=O)N)C(=CN2)CCN

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = 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 an agonist of the 5-HT₂, 5-HT₃, 5-HT₆ receptors with lower affinity.{{cite journal | vauthors = Yamada J, Sugimoto Y, Noma T, Yoshikawa T | title = Effects of the non-selective 5-HT receptor agonist, 5-carboxamidotryptamine, on plasma glucose levels in rats | journal = European Journal of Pharmacology | volume = 359 | issue = 1 | pages = 81–86 | date = October 1998 | pmid = 9831297 | doi = 10.1016/S0014-2999(98)00617-7 }}{{cite journal | vauthors = Wright CE, Angus JA | title = 5-carboxamidotryptamine elicits 5-HT2 and 5-HT3 receptor-mediated cardiovascular responses in the conscious rabbit: evidence for 5-HT release from platelets | journal = Journal of Cardiovascular Pharmacology | volume = 13 | issue = 4 | pages = 557–564 | date = April 1989 | pmid = 2470992 | doi = 10.1097/00005344-198913040-00007 | doi-access = free }}{{cite web | url = http://www.acnp.org/g4/GN401000039/Ch039.html | title = Serotonin Receptor Subtypes and Ligands | access-date = 2008-04-11 |vauthors=Glennon RA, Dukat M, Westkaemper RB | date = 2000-01-01 | publisher = American College of Neurophyscopharmacology | archive-url= https://web.archive.org/web/20080421160353/http://www.acnp.org/g4/GN401000039/Ch039.html| archive-date= 21 April 2008 | url-status= live}}{{cite book | vauthors = van Wijngaarden I, Soudijn W | title=Pharmacochemistry Library | chapter=5-HT2A, 5-HT2B and 5-HT2C receptor ligands | publisher=Elsevier | volume=27 | date=1997 | isbn=978-0-444-82041-9 | doi=10.1016/s0165-7208(97)80013-x | page=161–197}} It has negligible affinity for the 5-HT_1E and 5-HT_1F receptors.{{cite journal | vauthors = Stanton JA, Middlemiss DN, Beer MS | title = Autoradiographic localization of 5-CT-insensitive 5-HT1-like recognition sites in guinea pig and rat brain | journal = Neuropharmacology | volume = 35 | issue = 2 | pages = 223–229 | date = February 1996 | pmid = 8734492 | doi = 10.1016/0028-3908(95)00178-6 | s2cid = 27188133 }} 5-CT binds most strongly to the 5-HT_1A receptor and it was once thought to be selective for this site.{{cite journal | vauthors = Thomas DR, Middlemiss DN, Taylor SG, Nelson P, Brown AM | title = 5-CT stimulation of adenylyl cyclase activity in guinea-pig hippocampus: evidence for involvement of 5-HT7 and 5-HT1A receptors | journal = British Journal of Pharmacology | volume = 128 | issue = 1 | pages = 158–164 | date = September 1999 | pmid = 10498847 | pmc = 1571602 | doi = 10.1038/sj.bjp.0702759 }}{{cite journal | vauthors = Saxena PR, Lawang A | title = A comparison of cardiovascular and smooth muscle effects of 5-hydroxytryptamine and 5-carboxamidotryptamine, a selective agonist of 5-HT1 receptors | journal = Archives Internationales de Pharmacodynamie et de Therapie | volume = 277 | issue = 2 | pages = 235–252 | date = October 1985 | pmid = 2933009 }}

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.{{cite journal | vauthors = Latacz G, Hogendorf AS, Hogendorf A, Lubelska A, Wierońska JM, Woźniak M, Cieślik P, Kieć-Kononowicz K, Handzlik J, Bojarski AJ | title = 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 | journal = MedChemComm | volume = 9 | issue = 11 | pages = 1882–1890 | date = November 2018 | pmid = 30568756 | pmc = 6256855 | doi = 10.1039/c8md00313k }} Structural study indicated residue Ser5x43 might play critical roles in the selectivity of 5-CT across the serotonin receptor family.{{cite journal | vauthors = Zhang S, Chen H, Zhang C, Yang Y, Popov P, Liu J, Krumm BE, Cao C, Kim K, Xiong Y, Katritch V, Shoichet BK, Jin J, Fay JF, Roth BL | title = Inactive and active state structures template selective tools for the human 5-HT_5A receptor | journal = Nature Structural & Molecular Biology | volume = 29 | issue = 7 | pages = 677–687 | date = July 2022 | pmid = 35835867 | pmc = 9299520 | doi = 10.1038/s41594-022-00796-6}}