Ergotamine
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Basic Info
| Common Name | Ergotamine(F04690) |
| 2D Structure | |
| Description | Ergotamine is only found in individuals that have used or taken this drug. It is a vasoconstrictor found in ergot of Central Europe. It is an alpha-1 selective adrenergic agonist and is commonly used in the treatment of migraine disorders. Ergotamine acts on migraine by one of two proposed mechanisms: 1) activation of 5-HT<sub>1D</sub> receptors located on intracranial blood vessels, including those on arterio-venous anastomoses, leads to vasoconstriction, which correlates with the relief of migraine headache, and 2) activation of 5-HT<sub>1D</sub> receptors on sensory nerve endings of the trigeminal system results in the inhibition of pro-inflammatory neuropeptide release. |
| FRCD ID | F04690 |
| CAS Number | 113-15-5 |
| PubChem CID | 8223 |
| Formula | C33H35N5O5 |
| IUPAC Name | None |
| InChI Key | XCGSFFUVFURLIX-VFGNJEKYSA-N |
| InChI | InChI=1S/C33H35N5O5/c1-32(35-29(39)21-15-23-22-10-6-11-24-28(22)20(17-34-24)16-25(23)36(2)18-21)31(41)38-26(14-19-8-4-3-5-9-19)30(40)37-13-7-12-27(37)33(38,42)43-32/h3-6,8-11,15,17,21,25-27,34,42H,7,12-14,16,18H2,1-2H3,(H,35,39)/t21-,25-,26+,27+,32-,33+/m1/s1 |
| Canonical SMILES | CC1(C(=O)N2C(C(=O)N3CCCC3C2(O1)O)CC4=CC=CC=C4)NC(=O)C5CN(C6CC7=CNC8=CC=CC(=C78)C6=C5)C |
| Isomeric SMILES | C[C@@]1(C(=O)N2[C@H](C(=O)N3CCC[C@H]3[C@@]2(O1)O)CC4=CC=CC=C4)NC(=O)[C@H]5CN([C@@H]6CC7=CNC8=CC=CC(=C78)C6=C5)C |
| Wikipedia | Ergotamine |
| Synonyms |
Ergotamina
ERGOTAMINE
Ergotamin
Gynergen
Ergostat
ergotaminum
Ergonsvine
Ergomar
113-15-5
ergotamine tartrate
|
| Classifies |
Fungal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Alkaloids and derivatives |
| Class | Ergoline and derivatives |
| Subclass | Lysergic acids and derivatives |
| Intermediate Tree Nodes | Ergopeptines |
| Direct Parent | Ergotamines, dihydroergotamines, and derivatives |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Ergotamine - Hybrid peptide - Alpha-dipeptide - Lysergic acid amide - Indoloquinoline - Benzoquinoline - Quinoline-3-carboxamide - N-acyl-alpha amino acid or derivatives - Pyrroloquinoline - Quinoline - Alpha-amino acid or derivatives - 3-alkylindole - Indole - Indole or derivatives - Isoindole or derivatives - Aralkylamine - N-alkylpiperazine - Monocyclic benzene moiety - 1,4-diazinane - Benzenoid - Oxazolidinone - Piperazine - Pyrrole - Pyrrolidine - Heteroaromatic compound - Oxazolidine - Tertiary carboxylic acid amide - Carboxamide group - Tertiary amine - Amino acid or derivatives - Lactam - Tertiary aliphatic amine - Secondary carboxylic acid amide - Orthocarboxylic acid derivative - Carboxylic acid derivative - Organoheterocyclic compound - Alkanolamine - Oxacycle - Azacycle - Organooxygen compound - Organic nitrogen compound - Organopnictogen compound - Carbonyl group - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Amine - Organonitrogen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as ergotamines, dihydroergotamines, and derivatives. These are organic compounds containing an ergotamine moiety, which is structurally characterized by a benzyl substituent attached to the piperazine ring of the ergopeptine backbone. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 581.673 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 4 |
| Complexity | 1220 |
| Monoisotopic Mass | 581.264 |
| Exact Mass | 581.264 |
| XLogP | 2 |
| Formal Charge | 0 |
| Heavy Atom Count | 43 |
| Defined Atom Stereocenter Count | 6 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB- | 0.9644 |
| Human Intestinal Absorption | HIA+ | 0.9311 |
| Caco-2 Permeability | Caco2- | 0.7317 |
| P-glycoprotein Substrate | Substrate | 0.8678 |
| P-glycoprotein Inhibitor | Inhibitor | 0.7801 |
| Inhibitor | 0.6032 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8178 |
| Distribution | ||
| Subcellular localization | Nucleus | 0.3523 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8205 |
| CYP450 2D6 Substrate | Non-substrate | 0.9116 |
| CYP450 3A4 Substrate | Substrate | 0.7408 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9107 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9071 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9230 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8849 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.7959 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6759 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8701 |
| Non-inhibitor | 0.6708 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.9604 |
| Fish Toxicity | High FHMT | 0.9966 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9383 |
| Honey Bee Toxicity | Low HBT | 0.6145 |
| Biodegradation | Not ready biodegradable | 0.9900 |
| Acute Oral Toxicity | III | 0.5646 |
| Carcinogenicity (Three-class) | Non-required | 0.5016 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.6786 | LogS |
| Caco-2 Permeability | 0.2331 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.9840 | LD50, mol/kg |
| Fish Toxicity | 1.1292 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.4953 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Detection of Total Ergot Alkaloids in Cereal Flour and in Bread by a Generic Enzyme Immunoassay Method. | J AOAC Int | 2018 May 1 | 28964275 |
| Development and validation of an ultrahigh performance liquid chromatography-high resolution tandem mass spectrometry assay for nine toxic alkaloids from endophyte-infected pasture grasses in horse serum. | J Chromatogr A | 2018 Jul 27 | 29779692 |
| Contractile Response of Bovine Lateral Saphenous Vein to Ergotamine Tartrate Exposed to Different Concentrations of Molecularly Imprinted Polymer. | Toxins (Basel) | 2018 Jan 30 | 29385697 |
| Effects of clay on toxin binding capacity, ruminal fermentation, diet digestibility, and growth of steers fed high-concentrate diets. | J Anim Sci | 2017 Oct | 29108043 |
| Vasoactivity and Vasoconstriction Changes in Cattle Related to Time off Toxic Endophyte-Infected Tall Fescue. | Toxins (Basel) | 2016 Sep 22 | 27669299 |
| Ergot alkaloids: From witchcraft till in silico analysis. Multi-receptor analysisof ergotamine metabolites. | Toxicol Rep | 2015 Mar 23 | 28962389 |
| The role of the Oregon State University Endophyte Service Laboratory in diagnosing clinical cases of endophyte toxicoses. | J Agric Food Chem | 2014 Jul 30 | 25017309 |
| Dietary exposure to ergot alkaloids decreases contractility of bovine mesenteric vasculature. | J Anim Sci | 2014 Apr | 24492572 |
| Combined effects of fungal alkaloids on intestinal motility in an in vitro rat model. | J Anim Sci | 2013 Nov | 23989880 |
| Degradation and epimerization of ergot alkaloids after baking and in vitro digestion. | Anal Bioanal Chem | 2012 Nov | 22968686 |
| Constriction of bovine vasculature caused by endophyte-infected tall fescue seed extract is similar to pure ergovaline. | J Anim Sci | 2012 May | 22147482 |
| Permeability of ergot alkaloids across the blood-brain barrier in vitro andinfluence on the barrier integrity. | Mol Nutr Food Res | 2012 Mar | 22147614 |
| Dysgalactia associated with Mycoplasma suis infection in a sow herd. | J Am Vet Med Assoc | 2012 Dec 15 | 23216044 |
| Effect of ergot alkaloids on contractility of bovine right ruminal artery and vein. | J Anim Sci | 2011 Sep | 21512122 |
| Mycotoxins in foods in Lower Saxony (Germany): results of official control analyses performed in 2009. | Mycotoxin Res | 2011 May | 23605704 |
| Bovine neuronal vesicular glutamate transporter activity is inhibited byergovaline and other ergopeptines. | J Dairy Sci | 2011 Jul | 21700019 |
| Cluster headache. | BMJ Clin Evid | 2010 Feb 9 | 21718584 |
| Ergot alkaloids in rye flour determined by solid-phase cation-exchange andhigh-pressure liquid chromatography with fluorescence detection. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2008Mar | 18311624 |
| Effects of the ergot alkaloids dihydroergotamine, ergonovine, and ergotamine ongrowth of Escherichia coli O157:H7 in vitro. | Foodborne Pathog Dis | 2008 Oct | 18681792 |
| Determination of ergot alkaloids: purity and stability assessment of standardsand optimization of extraction conditions for cereal samples. | J AOAC Int | 2008 Nov-Dec | 19202797 |
Targets
- General Function:
- Protein homodimerization activity
- Specific Function:
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins.
- Gene Name:
- ADRA2C
- Uniprot ID:
- P18825
- Molecular Weight:
- 49521.585 Da
- Mechanism of Action:
- Ergotamine acts as an agonist at alpha-adrenergic receptors, causing vasoconstriction.
References
- Valdivia LF, Centurion D, Arulmani U, Saxena PR, Villalon CM: 5-HT1B receptors, alpha2A/2C- and, to a lesser extent, alpha1-adrenoceptors mediate the external carotid vasoconstriction to ergotamine in vagosympathectomised dogs. Naunyn Schmiedebergs Arch Pharmacol. 2004 Jul;370(1):46-53. Epub 2004 Jun 29. [15224175 ]
- Uniprot ID:
- P21728; P21918
References
- Bigal ME, Tepper SJ: Ergotamine and dihydroergotamine: a review. Curr Pain Headache Rep. 2003 Feb;7(1):55-62. [12525272 ]
- General Function:
- Serotonin receptor activity
- Specific Function:
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various ergot alkaloid derivatives and psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and down-stream signaling cascades and promotes the release of Ca(2+) ions from intracellular stores. Plays a role in the regulation of dopamine and 5-hydroxytryptamine release, 5-hydroxytryptamine uptake and in the regulation of extracellular dopamine and 5-hydroxytryptamine levels, and thereby affects neural activity. May play a role in the perception of pain. Plays a role in the regulation of behavior, including impulsive behavior. Required for normal proliferation of embryonic cardiac myocytes and normal heart development. Protects cardiomyocytes against apoptosis. Plays a role in the adaptation of pulmonary arteries to chronic hypoxia. Plays a role in vasoconstriction. Required for normal osteoblast function and proliferation, and for maintaining normal bone density. Required for normal proliferation of the interstitial cells of Cajal in the intestine.
- Gene Name:
- HTR2B
- Uniprot ID:
- P41595
- Molecular Weight:
- 54297.41 Da
- Mechanism of Action:
- Ergotamine acts as an agonist at 5-HT2 receptors, causing vasoconstriction.
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
- General Function:
- Protein heterodimerization activity
- Specific Function:
- This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes.
- Gene Name:
- ADRA1A
- Uniprot ID:
- P35348
- Molecular Weight:
- 51486.005 Da
- Mechanism of Action:
- Ergotamine acts as an agonist at alpha-adrenergic receptors, causing vasoconstriction.
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Virus receptor activity
- Specific Function:
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates phospholipase C and a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and promotes the release of Ca(2+) ions from intracellular stores. Affects neural activity, perception, cognition and mood. Plays a role in the regulation of behavior, including responses to anxiogenic situations and psychoactive substances. Plays a role in intestinal smooth muscle contraction, and may play a role in arterial vasoconstriction.(Microbial infection) Acts as a receptor for human JC polyomavirus/JCPyV.
- Gene Name:
- HTR2A
- Uniprot ID:
- P28223
- Molecular Weight:
- 52602.58 Da
- Mechanism of Action:
- Ergotamine acts as an agonist at 5-HT2 receptors, causing vasoconstriction.
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
- General Function:
- Thioesterase binding
- Specific Function:
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol.
- Gene Name:
- ADRA2A
- Uniprot ID:
- P08913
- Molecular Weight:
- 48956.275 Da
- Mechanism of Action:
- Ergotamine acts as an agonist at alpha-adrenergic receptors, causing vasoconstriction.
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Epinephrine binding
- Specific Function:
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol.
- Gene Name:
- ADRA2B
- Uniprot ID:
- P18089
- Molecular Weight:
- 49565.8 Da
- Mechanism of Action:
- Ergotamine acts as an agonist at alpha-adrenergic receptors, causing vasoconstriction.
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Protein heterodimerization activity
- Specific Function:
- This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine (PE)-stimulated ERK signaling in cardiac myocytes.
- Gene Name:
- ADRA1B
- Uniprot ID:
- P35368
- Molecular Weight:
- 56835.375 Da
- Mechanism of Action:
- Ergotamine acts as an agonist at alpha-adrenergic receptors, causing vasoconstriction.
References
- Valdivia LF, Centurion D, Arulmani U, Saxena PR, Villalon CM: 5-HT1B receptors, alpha2A/2C- and, to a lesser extent, alpha1-adrenoceptors mediate the external carotid vasoconstriction to ergotamine in vagosympathectomised dogs. Naunyn Schmiedebergs Arch Pharmacol. 2004 Jul;370(1):46-53. Epub 2004 Jun 29. [15224175 ]
- General Function:
- Alpha1-adrenergic receptor activity
- Specific Function:
- This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium.
- Gene Name:
- ADRA1D
- Uniprot ID:
- P25100
- Molecular Weight:
- 60462.205 Da
- Mechanism of Action:
- Ergotamine acts as an agonist at alpha-adrenergic receptors, causing vasoconstriction.
References
- Valdivia LF, Centurion D, Arulmani U, Saxena PR, Villalon CM: 5-HT1B receptors, alpha2A/2C- and, to a lesser extent, alpha1-adrenoceptors mediate the external carotid vasoconstriction to ergotamine in vagosympathectomised dogs. Naunyn Schmiedebergs Arch Pharmacol. 2004 Jul;370(1):46-53. Epub 2004 Jun 29. [15224175 ]
- General Function:
- Potassium channel regulator activity
- Specific Function:
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
- Gene Name:
- DRD2
- Uniprot ID:
- P14416
- Molecular Weight:
- 50618.91 Da
- Mechanism of Action:
- Ergotamine acts as an agonist at D(2) dopamine receptors.
References
- Tfelt-Hansen P, Saxena PR, Dahlof C, Pascual J, Lainez M, Henry P, Diener H, Schoenen J, Ferrari MD, Goadsby PJ: Ergotamine in the acute treatment of migraine: a review and European consensus. Brain. 2000 Jan;123 ( Pt 1):9-18. [10611116 ]
- General Function:
- Norepinephrine:sodium symporter activity
- Specific Function:
- Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name:
- SLC6A2
- Uniprot ID:
- P23975
- Molecular Weight:
- 69331.42 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Serotonin receptor activity
- Specific Function:
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various alkaloids and psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling inhibits adenylate cyclase activity.
- Gene Name:
- HTR1F
- Uniprot ID:
- P30939
- Molecular Weight:
- 41708.505 Da
References
- Bigal ME, Tepper SJ: Ergotamine and dihydroergotamine: a review. Curr Pain Headache Rep. 2003 Feb;7(1):55-62. [12525272 ]
- General Function:
- Serotonin receptor activity
- Specific Function:
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling inhibits adenylate cyclase activity. Regulates the release of 5-hydroxytryptamine in the brain, and thereby affects neural activity. May also play a role in regulating the release of other neurotransmitters. May play a role in vasoconstriction.
- Gene Name:
- HTR1D
- Uniprot ID:
- P28221
- Molecular Weight:
- 41906.38 Da
- Mechanism of Action:
- Ergotamine acts as an agonist at 5-HT1D receptors located on intracranial blood vessels, including those on arterio-venous anastomoses, leading to vasoconstriction. It also activates 5-HT1D receptors on sensory nerve endings of the trigeminal system, resulting in the inhibition of pro-inflammatory neuropeptide release.
References
- Silberstein SD, McCrory DC: Ergotamine and dihydroergotamine: history, pharmacology, and efficacy. Headache. 2003 Feb;43(2):144-66. [12558771 ]
- General Function:
- Serotonin receptor activity
- Specific Function:
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive substances, such as lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling inhibits adenylate cyclase activity. Arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Regulates the release of 5-hydroxytryptamine, dopamine and acetylcholine in the brain, and thereby affects neural activity, nociceptive processing, pain perception, mood and behavior. Besides, plays a role in vasoconstriction of cerebral arteries.
- Gene Name:
- HTR1B
- Uniprot ID:
- P28222
- Molecular Weight:
- 43567.535 Da
- Mechanism of Action:
- Ergotamine acts as an agonist at 5-HT1B receptors located on intracranial blood vessels, including those on arterio-venous anastomoses, leading to vasoconstriction. It also activates 5-HT1B receptors on sensory nerve endings of the trigeminal system, resulting in the inhibition of pro-inflammatory neuropeptide release.
References
- Willems EW, Trion M, De Vries P, Heiligers JP, Villalon CM, Saxena PR: Pharmacological evidence that alpha1-and alpha2-adrenoceptors mediate vasoconstriction of carotid arteriovenous anastomoses in anaesthetized pigs. Br J Pharmacol. 1999 Jul;127(5):1263-71. [10455274 ]
- General Function:
- Serotonin receptor activity
- Specific Function:
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-iodophenyl-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and down-stream signaling cascades and promotes the release of Ca(2+) ions from intracellular stores. Regulates neuronal activity via the activation of short transient receptor potential calcium channels in the brain, and thereby modulates the activation of pro-opiomelacortin neurons and the release of CRH that then regulates the release of corticosterone. Plays a role in the regulation of appetite and eating behavior, responses to anxiogenic stimuli and stress. Plays a role in insulin sensitivity and glucose homeostasis.
- Gene Name:
- HTR2C
- Uniprot ID:
- P28335
- Molecular Weight:
- 51820.705 Da
- Mechanism of Action:
- Ergotamine acts as an agonist at 5-HT2 receptors, causing vasoconstriction.
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
- General Function:
- Serotonin receptor activity
- Specific Function:
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling inhibits adenylate cyclase activity and activates a phosphatidylinositol-calcium second messenger system that regulates the release of Ca(2+) ions from intracellular stores. Plays a role in the regulation of 5-hydroxytryptamine release and in the regulation of dopamine and 5-hydroxytryptamine metabolism. Plays a role in the regulation of dopamine and 5-hydroxytryptamine levels in the brain, and thereby affects neural activity, mood and behavior. Plays a role in the response to anxiogenic stimuli.
- Gene Name:
- HTR1A
- Uniprot ID:
- P08908
- Molecular Weight:
- 46106.335 Da
References
- Bigal ME, Tepper SJ: Ergotamine and dihydroergotamine: a review. Curr Pain Headache Rep. 2003 Feb;7(1):55-62. [12525272 ]