5-CARBOXAMIDOTRYPTAMINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H13N3O
Molecular Weight	203.2404
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NCCC1=CNC2=CC=C(C=C12)C(N)=O

InChI

InChIKey=WKZLNEWVIAGNAW-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Description
Sources: http://www.sciencedirect.com/science/article/pii/B9780080552323611304 | https://www.ncbi.nlm.nih.gov/pubmed/2937503 | https://www.ncbi.nlm.nih.gov/pubmed/14965244

5-carboxamidotryptamine (5-CT) is a 5-HT1 agonist with high affinity at 5-HT1A, 5-HT1B, 5-HT1D, 5-HT5 and 5-HT7 receptors. As one of the first compounds reported active at 5-HT1B, 5-carboxamidotryptamine was originally investigated as a potential treatment for migraine. During preclinical studies, 5-CT was found to cause vasodilatation of carotid circulation and hypotension in animals, effects that were later attributed to potent agonist activity at 5-HT7. Subsequent structural modifications of 5-CT led to the discovery of the anti-migraine drug sumatriptan. 5-CT is primarily used as a pharmacological tool for study of 5-HT1 and 5-HT7 mediated functional responses.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
Serotonin 1a (5-HT1a) receptor 172 Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14965244 \| https://www.ncbi.nlm.nih.gov/pubmed/9205951 \| https://www.ncbi.nlm.nih.gov/pubmed/1386736	Agonist 2678	0.3 nM [Ki]
Serotonin 7 (5-HT7) receptor 31 Target ID: CHEMBL3155 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10753471 \| https://www.ncbi.nlm.nih.gov/pubmed/8226867	Agonist 2678	0.029 nM [Ki]
Serotonin 1d (5-HT1d) receptor 52 Target ID: CHEMBL1983 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8863519 \| https://www.ncbi.nlm.nih.gov/pubmed/8967979	Agonist 2678	7.7 nM [Ki]
Serotonin 1b (5-HT1b) receptor 46 Target ID: CHEMBL1898 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14613313	Agonist 2678	8.9 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Migraine 103 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15821444 http://www.sciencedirect.com/science/article/pii/B9780080552323611304	Primary		Preclinical	Unknown Approved Use Unknown
Hypertension 567 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7781688	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Primary structure and functional characterization of a human 5-HT1D-type serotonin receptor.	1991 Aug	1652050
Mouse 5HT1B serotonin receptor: cloning, functional expression, and localization in motor control centers.	1992 Apr 1	1557407
Human serotonin 1D receptor is encoded by a subfamily of two distinct genes: 5-HT1D alpha and 5-HT1D beta.	1992 Apr 15	1565658
Molecular cloning of a serotonin receptor from human brain (5HT1E): a fifth 5HT1-like subtype.	1992 Jun 15	1608964
Serotonergic and dopaminergic influence of the duration of embryogenesis and intracapsular locomotion of Lymnaea stagnalis L.	2004	15270248
Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors.	2004 Aug	15322733
A 5-HT7 heteroreceptor-mediated inhibition of [3H]serotonin release in raphe nuclei slices of the rat: evidence for a serotonergic-glutamatergic interaction.	2004 Aug	15260125
Cloning and pharmacological characterisation of the guinea pig 5-ht5A receptor.	2004 Jun 28	15212962
Low-density lipoprotein inhibits receptor-mediated prostaglandin synthesis without affecting calcium and arachidonic acid mobilization in human endothelial cells.	2004 Nov	15505500
Cloned human 5-HT1A receptor pharmacology determined using agonist binding and measurement of cAMP accumulation.	2004 Oct	15482641
Functional expression of the serotonin 5-HT7 receptor in human glioblastoma cell lines.	2004 Oct	15339860
5-HT7 receptor efficacy distribution throughout the canine stomach.	2004 Oct	15339857
5-HT7, but not 5-HT2B, receptors mediate hypotension in vagosympathectomized rats.	2004 Oct 19	15476750
Environmental programming of stress responses through DNA methylation: life at the interface between a dynamic environment and a fixed genome.	2005	16262207
[The functional change in the 5-HT1A receptor induced by stress and the role of the 5-HT1A receptor in neuroprotection].	2005 Apr	16220659
Enhanced transcription of contractile 5-hydroxytryptamine 2A receptors via extracellular signal-regulated kinase 1/2 after organ culture of rat mesenteric artery.	2005 Apr	15755310
Sustained pharmacological blockade of NK1 substance P receptors causes functional desensitization of dorsal raphe 5-HT 1A autoreceptors in mice.	2005 Dec	16219031
Serotonin 5-HT7 receptors coupled to induction of interleukin-6 in human microglial MC-3 cells.	2005 Jul	15992579
Characterization of 5-HT7-receptor-mediated gastric relaxation in conscious dogs.	2005 Jul	15746214
5-HT receptors couple to activation of Akt, but not extracellular-regulated kinase (ERK), in cultured hippocampal neurons.	2005 May	15857394
Triptans induce vasoconstriction of human arteries and veins from the thoracic wall.	2005 May	15821444
Repeated administration of citalopram and imipramine alters the responsiveness of rat hippocampal circuitry to the activation of 5-HT7 receptors.	2005 Nov 7	16253236
Effect of 5-hydroxytryptamine on neurogenic vasoconstriction in the isolated, autoperfused hindquarters of the rat.	2005 Oct	16173953
Cyclic AMP mediates circadian phase shifts induced by microinjection of serotonergic drugs in the hamster dorsal raphe nucleus.	2005 Oct 5	16150426
Pronociceptive role of peripheral and spinal 5-HT7 receptors in the formalin test.	2005 Sep	16098671
Pharmacological characterization of 5-hydroxytryptamine-induced contraction in the chicken gastrointestinal tract.	2006 Apr	16553644
Heterologous desensitization is evoked by both agonist and antagonist stimulation of the human 5-HT(7) serotonin receptor.	2006 Feb 17	16487959
Contractile effects of 5-hydroxytryptamine and 5-carboxamidotryptamine in the equine jejunum.	2006 Jan	16230998
ERK1/2 inhibition attenuates cerebral blood flow reduction and abolishes ET(B) and 5-HT(1B) receptor upregulation after subarachnoid hemorrhage in rat.	2006 Jun	16251886
Properties and opioid inhibition of mesolimbic dopamine neurons vary according to target location.	2006 Mar 8	16525058
Functional and molecular identification of 5-hydroxytryptamine receptors in rabbit pulmonary artery: involvement in complex regulation of noradrenaline release.	2006 Mar-Apr	16702620
Gender-dependent regulation of G-protein-gated inwardly rectifying potassium current in dorsal raphe neurons in knock-out mice devoid of the 5-hydroxytryptamine transporter.	2006 Nov	17013926
Effects of genetic background and null mutation of 5-HT1A receptors on basal and stress-induced body temperature: modulation by serotonergic and GABAA-ergic drugs.	2006 Nov 21	17022970
Paradoxical striatal cellular signaling responses to psychostimulants in hyperactive mice.	2006 Oct 27	16954211
Am5-HT7: molecular and pharmacological characterization of the first serotonin receptor of the honeybee (Apis mellifera).	2006 Sep	16945110
Regional differences in the coupling of 5-hydroxytryptamine-1A receptors to G proteins in the rat brain.	2006 Sep	16772521
The role of 5-HT(7) receptors in the control of seizures.	2007 Apr 13	17276417
Pharmacology of serotonin-induced salivary secretion in Periplaneta americana.	2007 Aug	17475273
Cooling augments vasoconstriction mediated by 5-HT1 and alpha2-adrenoceptors in the isolated equine digital vein: involvement of Rho kinase.	2007 Aug 27	17560569
The 5HT(7) receptor subtype is involved in the regulation of female sexual behaviour in the rat.	2007 Aug-Sep	17561239
Pharmacological evidence that 5-HT(1B/1D) receptors mediate hypotension in anesthetized rats.	2007 Dec 8	17727836
Protein kinase C inhibition prevents upregulation of vascular ET(B) and 5-HT(1B) receptors and reverses cerebral blood flow reduction after subarachnoid haemorrhage in rats.	2007 Jan	16736053
Effect of long-term administration of the antidepressant drug milnacipran on serotonergic and noradrenergic neurotransmission in the rat hippocampus.	2007 Jun 20	17568622
5-HT7 receptor-mediated dilatation in the middle meningeal artery of anesthetized rats.	2007 Mar 29	17316605
Neurokinin-1 receptor antagonism in a rat model of subarachnoid hemorrhage: prevention of upregulation of contractile ETB and 5-HT1B receptors and cerebral blood flow reduction.	2007 May	17542534
Diabetes-induced changes in 5-hydroxytryptamine modulation of vagally-induced bradycardia in rat heart.	2007 Nov	17880377
Effects of repetitive administration of tianeptine, zinc hydroaspartate and electroconvulsive shock on the reactivity of 5-HT(7) receptors in rat hippocampus.	2007 Nov-Dec	18195451
Attenuating effects of prior oestradiol benzoate priming on 5-HT-mediated lordosis behavior in rats are dose-dependent.	2007 Sep	17853773
Heterogeneity in 5-HT-induced contractile and proliferative responses in rat pulmonary arterial bed.	2008	18025789
5-HT1B receptor subtype and aging in rat resistance vessels.	2008	17917465

Patents

Sample Use Guides

In Vivo Use Guide

Rats: 5-carboxamidotryptamine (5-CT) above the dosage of 0.05 mg/kg elicited significant hyperglycemic effects and 0.1 mg/kg, induced a 35% increase in plasma glucose levels.

Route of Administration: Intraperitoneal

In Vitro Use Guide

5-carboxamidotryptamine (5-CT; 0.3 uM) inhibited electrical field stimulation (EFS)-induced contractions of dog antrum longitudinal muscle in vitro.

Name

Type

Language

5-CARBOXAMIDOTRYPTAMINE

Common Name

English

1H-INDOLE-5-CARBOXAMIDE, 3-(2-AMINOETHYL)-

Systematic Name

English

Code System Code Type Description

CAS

74885-09-9