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
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)
| Molecular Formula | C11H13N3O |
| Molecular Weight | 203.2404 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Heterogeneity in 5-HT-induced contractile and proliferative responses in rat pulmonary arterial bed. | 2008 |
|
| 5-HT1B receptor subtype and aging in rat resistance vessels. | 2008 |
|
| Pharmacological evidence that 5-HT(1B/1D) receptors mediate hypotension in anesthetized rats. | 2007-12-08 |
|
| Diabetes-induced changes in 5-hydroxytryptamine modulation of vagally-induced bradycardia in rat heart. | 2007-11 |
|
| Attenuating effects of prior oestradiol benzoate priming on 5-HT-mediated lordosis behavior in rats are dose-dependent. | 2007-09 |
|
| Cooling augments vasoconstriction mediated by 5-HT1 and alpha2-adrenoceptors in the isolated equine digital vein: involvement of Rho kinase. | 2007-08-27 |
|
| 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 |
|
| Pharmacology of serotonin-induced salivary secretion in Periplaneta americana. | 2007-08 |
|
| Effect of long-term administration of the antidepressant drug milnacipran on serotonergic and noradrenergic neurotransmission in the rat hippocampus. | 2007-06-20 |
|
| 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 |
|
| The role of 5-HT(7) receptors in the control of seizures. | 2007-04-13 |
|
| The 5HT(7) receptor subtype is involved in the regulation of female sexual behaviour in the rat. | 2007-04-03 |
|
| 5-HT7 receptor-mediated dilatation in the middle meningeal artery of anesthetized rats. | 2007-03-29 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Paradoxical striatal cellular signaling responses to psychostimulants in hyperactive mice. | 2006-10-27 |
|
| Am5-HT7: molecular and pharmacological characterization of the first serotonin receptor of the honeybee (Apis mellifera). | 2006-09 |
|
| Regional differences in the coupling of 5-hydroxytryptamine-1A receptors to G proteins in the rat brain. | 2006-09 |
|
| 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 |
|
| Pharmacological characterization of 5-hydroxytryptamine-induced contraction in the chicken gastrointestinal tract. | 2006-04 |
|
| Properties and opioid inhibition of mesolimbic dopamine neurons vary according to target location. | 2006-03-08 |
|
| Functional and molecular identification of 5-hydroxytryptamine receptors in rabbit pulmonary artery: involvement in complex regulation of noradrenaline release. | 2006-02-27 |
|
| Heterologous desensitization is evoked by both agonist and antagonist stimulation of the human 5-HT(7) serotonin receptor. | 2006-02-17 |
|
| Contractile effects of 5-hydroxytryptamine and 5-carboxamidotryptamine in the equine jejunum. | 2006-01 |
|
| Sustained pharmacological blockade of NK1 substance P receptors causes functional desensitization of dorsal raphe 5-HT 1A autoreceptors in mice. | 2005-12 |
|
| Repeated administration of citalopram and imipramine alters the responsiveness of rat hippocampal circuitry to the activation of 5-HT7 receptors. | 2005-11-07 |
|
| Cyclic AMP mediates circadian phase shifts induced by microinjection of serotonergic drugs in the hamster dorsal raphe nucleus. | 2005-10-05 |
|
| Effect of 5-hydroxytryptamine on neurogenic vasoconstriction in the isolated, autoperfused hindquarters of the rat. | 2005-10 |
|
| Pronociceptive role of peripheral and spinal 5-HT7 receptors in the formalin test. | 2005-09 |
|
| Serotonin 5-HT7 receptors coupled to induction of interleukin-6 in human microglial MC-3 cells. | 2005-07 |
|
| Characterization of 5-HT7-receptor-mediated gastric relaxation in conscious dogs. | 2005-07 |
|
| 5-HT receptors couple to activation of Akt, but not extracellular-regulated kinase (ERK), in cultured hippocampal neurons. | 2005-05 |
|
| Triptans induce vasoconstriction of human arteries and veins from the thoracic wall. | 2005-05 |
|
| [The functional change in the 5-HT1A receptor induced by stress and the role of the 5-HT1A receptor in neuroprotection]. | 2005-04 |
|
| Enhanced transcription of contractile 5-hydroxytryptamine 2A receptors via extracellular signal-regulated kinase 1/2 after organ culture of rat mesenteric artery. | 2005-04 |
|
| Environmental programming of stress responses through DNA methylation: life at the interface between a dynamic environment and a fixed genome. | 2005 |
|
| Low-density lipoprotein inhibits receptor-mediated prostaglandin synthesis without affecting calcium and arachidonic acid mobilization in human endothelial cells. | 2004-11 |
|
| 5-HT7, but not 5-HT2B, receptors mediate hypotension in vagosympathectomized rats. | 2004-10-19 |
|
| Cloned human 5-HT1A receptor pharmacology determined using agonist binding and measurement of cAMP accumulation. | 2004-10 |
|
| Functional expression of the serotonin 5-HT7 receptor in human glioblastoma cell lines. | 2004-10 |
|
| 5-HT7 receptor efficacy distribution throughout the canine stomach. | 2004-10 |
|
| Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors. | 2004-08 |
|
| 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 |
|
| Cloning and pharmacological characterisation of the guinea pig 5-ht5A receptor. | 2004-06-28 |
|
| Serotonergic and dopaminergic influence of the duration of embryogenesis and intracapsular locomotion of Lymnaea stagnalis L. | 2004 |
|
| Molecular cloning of a serotonin receptor from human brain (5HT1E): a fifth 5HT1-like subtype. | 1992-06-15 |
|
| Human serotonin 1D receptor is encoded by a subfamily of two distinct genes: 5-HT1D alpha and 5-HT1D beta. | 1992-04-15 |
|
| Mouse 5HT1B serotonin receptor: cloning, functional expression, and localization in motor control centers. | 1992-04-01 |
|
| Primary structure and functional characterization of a human 5-HT1D-type serotonin receptor. | 1991-08 |
Sample Use Guides
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:53:52 GMT 2025
by
admin
on
Mon Mar 31 19:53:52 GMT 2025
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| Record UNII |
91H76044O0
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| Record Status |
Validated (UNII)
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| Record Version |
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1809
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91H76044O0
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C047087
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5-CARBOXAMIDOTRYPTAMINE
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DTXSID60996379
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