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=C1C=C(C=C2)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 177 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 2752	0.3 nM [Ki]
Serotonin 7 (5-HT7) receptor 30 Target ID: CHEMBL3155 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10753471 \| https://www.ncbi.nlm.nih.gov/pubmed/8226867	Agonist 2752	0.029 nM [Ki]
Serotonin 1d (5-HT1d) receptor 53 Target ID: CHEMBL1983 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8863519 \| https://www.ncbi.nlm.nih.gov/pubmed/8967979	Agonist 2752	7.7 nM [Ki]
Serotonin 1b (5-HT1b) receptor 45 Target ID: CHEMBL1898 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14613313	Agonist 2752	8.9 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Migraine 107 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15821444 http://www.sciencedirect.com/science/article/pii/B9780080552323611304	Primary		Preclinical	Unknown Approved Use Unknown
Hypertension 575 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7781688	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
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
Pharmacological evidence that 5-HT(1B/1D) receptors mediate hypotension in anesthetized rats.	2007-12-08	17727836
Diabetes-induced changes in 5-hydroxytryptamine modulation of vagally-induced bradycardia in rat heart.	2007-11	17880377
Attenuating effects of prior oestradiol benzoate priming on 5-HT-mediated lordosis behavior in rats are dose-dependent.	2007-09	17853773
Cooling augments vasoconstriction mediated by 5-HT1 and alpha2-adrenoceptors in the isolated equine digital vein: involvement of Rho kinase.	2007-08-27	17560569
Effects of repetitive administration of tianeptine, zinc hydroaspartate and electroconvulsive shock on the reactivity of 5-HT(7) receptors in rat hippocampus.	2007-08-26	18195451
Pharmacology of serotonin-induced salivary secretion in Periplaneta americana.	2007-08	17475273
Effect of long-term administration of the antidepressant drug milnacipran on serotonergic and noradrenergic neurotransmission in the rat hippocampus.	2007-06-20	17568622
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.	2007-05	17542534
The role of 5-HT(7) receptors in the control of seizures.	2007-04-13	17276417
The 5HT(7) receptor subtype is involved in the regulation of female sexual behaviour in the rat.	2007-04-03	17561239
5-HT7 receptor-mediated dilatation in the middle meningeal artery of anesthetized rats.	2007-03-29	17316605
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.	2007-01	16736053
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.	2006-11-21	17022970
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.	2006-11	17013926
Paradoxical striatal cellular signaling responses to psychostimulants in hyperactive mice.	2006-10-27	16954211
Am5-HT7: molecular and pharmacological characterization of the first serotonin receptor of the honeybee (Apis mellifera).	2006-09	16945110
Regional differences in the coupling of 5-hydroxytryptamine-1A receptors to G proteins in the rat brain.	2006-09	16772521
ERK1/2 inhibition attenuates cerebral blood flow reduction and abolishes ET(B) and 5-HT(1B) receptor upregulation after subarachnoid hemorrhage in rat.	2006-06	16251886
Pharmacological characterization of 5-hydroxytryptamine-induced contraction in the chicken gastrointestinal tract.	2006-04	16553644
Properties and opioid inhibition of mesolimbic dopamine neurons vary according to target location.	2006-03-08	16525058
Functional and molecular identification of 5-hydroxytryptamine receptors in rabbit pulmonary artery: involvement in complex regulation of noradrenaline release.	2006-02-27	16702620
Heterologous desensitization is evoked by both agonist and antagonist stimulation of the human 5-HT(7) serotonin receptor.	2006-02-17	16487959
Contractile effects of 5-hydroxytryptamine and 5-carboxamidotryptamine in the equine jejunum.	2006-01	16230998
Sustained pharmacological blockade of NK1 substance P receptors causes functional desensitization of dorsal raphe 5-HT 1A autoreceptors in mice.	2005-12	16219031
Repeated administration of citalopram and imipramine alters the responsiveness of rat hippocampal circuitry to the activation of 5-HT7 receptors.	2005-11-07	16253236
Cyclic AMP mediates circadian phase shifts induced by microinjection of serotonergic drugs in the hamster dorsal raphe nucleus.	2005-10-05	16150426
Effect of 5-hydroxytryptamine on neurogenic vasoconstriction in the isolated, autoperfused hindquarters of the rat.	2005-10	16173953
Pronociceptive role of peripheral and spinal 5-HT7 receptors in the formalin test.	2005-09	16098671
Serotonin 5-HT7 receptors coupled to induction of interleukin-6 in human microglial MC-3 cells.	2005-07	15992579
Characterization of 5-HT7-receptor-mediated gastric relaxation in conscious dogs.	2005-07	15746214
5-HT receptors couple to activation of Akt, but not extracellular-regulated kinase (ERK), in cultured hippocampal neurons.	2005-05	15857394
Triptans induce vasoconstriction of human arteries and veins from the thoracic wall.	2005-05	15821444
[The functional change in the 5-HT1A receptor induced by stress and the role of the 5-HT1A receptor in neuroprotection].	2005-04	16220659
Enhanced transcription of contractile 5-hydroxytryptamine 2A receptors via extracellular signal-regulated kinase 1/2 after organ culture of rat mesenteric artery.	2005-04	15755310
Environmental programming of stress responses through DNA methylation: life at the interface between a dynamic environment and a fixed genome.	2005	16262207
Low-density lipoprotein inhibits receptor-mediated prostaglandin synthesis without affecting calcium and arachidonic acid mobilization in human endothelial cells.	2004-11	15505500
5-HT7, but not 5-HT2B, receptors mediate hypotension in vagosympathectomized rats.	2004-10-19	15476750
Cloned human 5-HT1A receptor pharmacology determined using agonist binding and measurement of cAMP accumulation.	2004-10	15482641
Functional expression of the serotonin 5-HT7 receptor in human glioblastoma cell lines.	2004-10	15339860
5-HT7 receptor efficacy distribution throughout the canine stomach.	2004-10	15339857
Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors.	2004-08	15322733
A 5-HT7 heteroreceptor-mediated inhibition of [3H]serotonin release in raphe nuclei slices of the rat: evidence for a serotonergic-glutamatergic interaction.	2004-08	15260125
Cloning and pharmacological characterisation of the guinea pig 5-ht5A receptor.	2004-06-28	15212962
Serotonergic and dopaminergic influence of the duration of embryogenesis and intracapsular locomotion of Lymnaea stagnalis L.	2004	15270248
Molecular cloning of a serotonin receptor from human brain (5HT1E): a fifth 5HT1-like subtype.	1992-06-15	1608964
Human serotonin 1D receptor is encoded by a subfamily of two distinct genes: 5-HT1D alpha and 5-HT1D beta.	1992-04-15	1565658
Mouse 5HT1B serotonin receptor: cloning, functional expression, and localization in motor control centers.	1992-04-01	1557407
Primary structure and functional characterization of a human 5-HT1D-type serotonin receptor.	1991-08	1652050

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)-

Preferred Name

English

Code System Code Type Description

CAS

74885-09-9