Dihydroergotamine (CED0005910)

Record Information

Version

1.0

Creation Date

2009-07-21 20:26:35 UTC

Update Date

2026-05-14 16:25:23 UTC

SynCED ID

CED0005910

Secondary Accession Numbers

CHEM002169
T3D2750

Identification

Common Name

Dihydroergotamine

Class

Small Molecule

Description

Dihydroergotamine belongs to the lysergic acids and derivatives, a subclass of ergoline and derivatives within the organic compounds. With an average molecular weight of 583.68 g/mol, Dihydroergotamine is a heavy molecule. This exogenous compound has the formula C33H37N5O5 and exists as a solid at room temperature. It is utilized as a vasoconstrictor agent, a non-narcotic analgesic, and a serotonergic agonist. Recorded exposure routes include intravenous, intramuscular, subcutaneous, and nasal administration. The substance is found in several recorded sources, including analgesics within healthcare, pharmaceuticals, and veterinary products; food preservation within food, food processing, and cookware; electric hearing aids and electrically stimulated smoking devices within electrical and electronic equipment; and various household cleaning and consumer products, such as perfumes within detergents and soaps, tobacco product cases, cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. Dihydroergotamine targets 23 proteins, including the Alpha-2A adrenergic receptor (ADRA2A), Solute carrier family 22 member 2 (SLC22A2), Cytochrome P450 3A4 (CYP3A4), Multidrug and toxin extrusion protein 2 (SLC47A2), and 12 other proteins. It acts as an agonist at the 5-HT receptors, specifically targeting 5-hydroxytryptamine receptors 1A (HTR1A), 1B (HTR1B), 1D (HTR1D), and 2A (HTR2A). It is believed to alleviate migraines through two possible mechanisms: the activation of 5-HT receptors on sensory nerve endings of the trigeminal system, resulting in the inhibition of pro-inflammatory neuropeptide release, or the activation of 5-HT receptors located on intracranial blood vessels, including those on arterio-venous anastomoses, which leads to vasoconstriction.

Contaminant Type

Amide
Amine
Analgesic
Analgesic, Non-Narcotic
Anti-Migraine Agent
Dopamine Agonist
Drug
Ether
Human Neurotoxin
Metabolite
Organic Compound
Sympatholytic
Synthetic Compound
Vasoconstrictor Agent

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5'-Benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxo-9,10-dihydroergotaman	ChEBI
9,10-Dihydro-12'-hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione	ChEBI
9,10-Dihydroergotamine	ChEBI
Dihidroergotamina	ChEBI
Dihydroergotaminum	ChEBI
Neomigran	Kegg
9,10-Dihydro-ergotamine	HMDB
Dihydroergotamine mesylate	HMDB
Dihydroergotamine methanesulfonate	HMDB
Dihydroergotamine monomethanesulfonate	HMDB
Clavigrenin	HMDB
D Tamin retard l.u.t.	HMDB
D.H.E. 45	HMDB
DHE 45	HMDB
DHE ratiopharm	HMDB
Desitin brand OF dihydroergotamine mesylate	HMDB
Methanesulfonate, dihydroergotamine	HMDB
Orstanorm	HMDB
Shire brand OF dihydroergotamine mesylate	HMDB
Wernigeroide brand OF dihydroergotamine mesylate	HMDB
Alpharma brand OF dihydroergotamine mesylate	HMDB
Angionorm	HMDB
Anto brand OF dihydroergotamine mesylate	HMDB
DHE-puren	HMDB
Dihydroergotamine-sandoz	HMDB
Ergomimet	HMDB
IPRAD brand OF dihydroergotamine mesylate	HMDB
Ikaran	HMDB
Migranal	HMDB
Pierre fabre brand OF dihydroergotamine mesylate	HMDB
Seglor	HMDB
Xcel brand 2 OF dihydroergotamine mesylate	HMDB
CT Arzneimittel brand OF dihydroergotamine mesylate	HMDB
CT-Arzneimittel brand OF dihydroergotamine mesylate	HMDB
Agit	HMDB
DET MS	HMDB
DHE puren	HMDB
DHE-ratiopharm	HMDB
DHE45	HMDB
Dihydroergotamin al	HMDB
Dihytamin	HMDB
Erganton	HMDB
Farmasan brand OF dihydroergotamine mesylate	HMDB
Q-Pharm brand OF dihydroergotamine mesylate	HMDB
Tamik	HMDB
Verla brand OF dihydroergotamine mesylate	HMDB
Xcel brand 1 OF dihydroergotamine mesylate	HMDB
Ergotam von CT	HMDB
Aliud brand OF dihydroergotamine mesylate	HMDB
D-Tamin retard l.u.t.	HMDB
DHE-45	HMDB
Dihydergot	HMDB
Dihydroergotamine sandoz	HMDB
Ergont	HMDB
Fujisawa brand OF dihydroergotamine mesylate	HMDB
Hormosan brand OF dihydroergotamine mesylate	HMDB
Mesylate, dihydroergotamine	HMDB
Novartis brand OF dihydroergotamine mesylate	HMDB
Pharmafrid brand OF dihydroergotamine mesylate	HMDB
Q Pharm brand OF dihydroergotamine mesylate	HMDB
Sanol brand OF dihydroergotamine mesylate	HMDB
Schwarz brand OF dihydroergotamine mesylate	HMDB
Verladyn	HMDB
Ratiopharm brand OF dihydroergotamine mesylate	HMDB
Von CT, ergotam	HMDB

Chemical Formula

C₃₃H₃₇N₅O₅

Average Molecular Mass

583.677 g/mol

Monoisotopic Mass

583.279 g/mol

CAS Registry Number

6190-39-2

IUPAC Name

(2R,4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraene-4-carboxamide

Traditional Name

dihydroergotamine

SMILES

[H][C@@]12CCCN1C(=O)[C@H](CC1=CC=CC=C1)N1C(=O)[C@](C)(NC(=O)[C@H]3CN(C)[C@]4([H])CC5=CNC6=CC=CC(=C56)[C@@]4([H])C3)O[C@@]21O

InChI Identifier

InChI=1S/C33H37N5O5/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/h3-6,8-11,17,21,23,25-27,34,42H,7,12-16,18H2,1-2H3,(H,35,39)/t21-,23-,25-,26+,27+,32-,33+/m1/s1

InChI Key

LUZRJRNZXALNLM-JGRZULCMSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ergoline and derivatives

Sub Class

Lysergic acids and derivatives

Direct Parent

Ergotamines, dihydroergotamines, and derivatives

Alternative Parents

Substituents

Dihydroergotamine
Ergotamine
Hybrid peptide
Alpha-dipeptide
Lysergic acid amide
Indoloquinoline
Benzoquinoline
Quinoline-3-carboxamide
N-acyl-alpha amino acid or derivatives
Pyrroloquinoline
Alpha-amino acid or derivatives
Quinoline
3-alkylindole
Indole
Indole or derivatives
Isoindole or derivatives
Piperidinecarboxamide
3-piperidinecarboxamide
Aralkylamine
N-alkylpiperazine
Benzenoid
Monocyclic benzene moiety
1,4-diazinane
Oxazolidinone
Piperazine
Piperidine
Tertiary carboxylic acid amide
Heteroaromatic compound
Oxazolidine
Pyrrolidine
Pyrrole
Amino acid or derivatives
Lactam
Tertiary aliphatic amine
Secondary carboxylic acid amide
Orthocarboxylic acid derivative
Carboxamide group
Tertiary amine
Oxacycle
Organoheterocyclic compound
Azacycle
Alkanolamine
Carboxylic acid derivative
Organonitrogen compound
Organic oxygen compound
Organopnictogen compound
Carbonyl group
Organic nitrogen compound
Amine
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

ergot alkaloid (CHEBI:4562 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	2.29e-01 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.23 g/L	ALOGPS
logP	3.04	ALOGPS
logP	2.71	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.71	ChemAxon
pKa (Strongest Basic)	8.39	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	118.21 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	159.39 m³·mol⁻¹	ChemAxon
Polarizability	63.3 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0fr5-5891210000-f53c38352e2598f9007e	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0fdn-7491022000-6c73d0337e04ab2f6918	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0022090000-bfd200952b03e8b137ff	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0un9-0091010000-c5661ba02ab58100d046	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-4590000000-dc4a0cca36e4ae6c18c5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0019-0049160000-4fdc70b6d84db2eb175e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03xr-2196220000-3c3fcf127102792f663c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0g4j-9810000000-88f13186254d2bf07e89	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0000090000-3abf973bfa14967f7f1d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0010290000-1037c6e147fa5f93e653	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0090010000-f5347f35594f87c4297f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0000090000-10b01aae8e192c05edc6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-2100390000-475a2b73d09ae5f9c174	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0v03-9351430000-9c41d997e0687489c4ee	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
703.0 Log mg/kg [400:1200]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Two theories have been proposed to explain the efficacy of 5-HT_1D receptor agonists in migraine: 1) activation of 5-HT_1D 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_1D receptors on sensory nerve endings of the trigeminal system results in the inhibition of pro-inflammatory neuropeptide release.

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Minimum Risk Level

Not Available

Symptoms

Convulsive ergotism can cause painful seizures and spasms, diarrhea, paresthesias, itching, headaches, nausea and vomiting. Usually the gastrointestinal effects precede the central nervous system effects. As well as seizures there can be hallucinations and mental effects including mania or psychosis. Gangrenous ergotism causes dry gangrene as a result of vasoconstriction induced in the more poorly vascularized distal structures, such as the fingers and toes. Symptoms include desquamation, weak periphery pulse, loss of peripheral sensation, edema and ultimately the death and loss of affected tissues. (9, 12)

Treatment

Treatment for ergotism consists of vasodilators, anticoagulants and low molecular weight dextrans. If necessary, a sympathetic nerve blockade may be carried out, such as brachial plexus blockade. Temporary sedation (e.g. haloperidol) will be necessary in hallucination and diazepam is used for convulsions. There is no specific antidote. (10, 12)

Health Effects

Health Effect	Relationship	Direction	Description	Reference
migraine	Not Available	Not Available	A brain disease that is characterized by moderate to severe headaches, nausea, extreme sensitivity to light and sound and intense unilaterial throbbing or pulsing. (DO)	PMC12560784

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000370	Analgesics?Analgesics are a class of synthetic chemicals designed to alleviate pain.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000516	Electric Hearing Aids?Electric hearing aids are small electronic devices designed to amplify sound for individuals with hearing loss.	Electrical & Electronic Equipment	PubChem
CEDs000518	Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.	Electrical & Electronic Equipment	PubChem
CEDs000545	Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.	Food, food processing & cookware	PubChem
CEDs000556	Cigar Cigarettes?Cigar cigarettes are a source of synthetic chemical contamination due to the combustion of various tobacco blends and additives.	Household cleaning & consumer products	PubChem
CEDs000559	Non Electric Simulated Smoking Devices?Non-electric simulated smoking devices, often designed to mimic the experience of smoking without combustion, can be sources of synthetic chemical contamination due to the materials and chemicals used in their construction and operation.	Household cleaning & consumer products	PubChem
CEDs000560	Other Smoking Requisites?Other smoking requisites, including items such as lighters, matches, and rolling papers, can introduce synthetic chemical contamination through various components and additives.	Household cleaning & consumer products	PubChem
CEDs000561	Perfumes Within Detergents And Soaps?Perfumes within detergents and soaps are synthetic fragrance compounds added to enhance the sensory experience of cleaning products.	Household cleaning & consumer products	PubChem
CEDs000567	Tobacco Product Cases?Tobacco product cases can serve as a source of synthetic chemical contamination due to the presence of various additives and chemicals used in tobacco processing and product manufacturing.	Household cleaning & consumer products	PubChem
CEDs000569	Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.	Household cleaning & consumer products	PubChem
CEDs000580	Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.	Industrial manufacturing & chemical processing	PubChem
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000613	Depilatories?Depilatories are products designed to remove unwanted hair through the application of synthetic chemicals that break down the protein structure of hair, facilitating its removal.	Personal care & cosmetics	PubChem
CEDs000614	Essential Oils Or Perfumes?Essential oils and perfumes are complex mixtures of volatile compounds derived from natural or synthetic sources, commonly used for their aromatic properties.	Personal care & cosmetics	PubChem
CEDs000615	Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.	Personal care & cosmetics	PubChem
CEDs000618	Lip Makeup Products?Lip makeup products, such as lipsticks, lip glosses, and lip liners, often contain a variety of synthetic chemicals, including pigments, preservatives, and emollients.	Personal care & cosmetics	PubChem
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	PubChem
CEDs000642	Footwear?Footwear production often involves the use of various synthetic chemicals, such as adhesives, dyes, and treatments, which can contribute to environmental contamination.	Textiles, leather & furnishings	PubChem
CEDs000650	Purses Luggage Hand Bags?Purses, luggage, and handbags are often manufactured using synthetic materials such as polyvinyl chloride (PVC), polyurethane, and various types of nylon.	Textiles, leather & furnishings	PubChem
CEDs000651	Purses Money Bags Wallets?Purses, money bags, and wallets are often manufactured using synthetic materials, including plastics, polyurethanes, and various treated fabrics.	Textiles, leather & furnishings	PubChem
CEDs000671	Airplanes And Helicopters?Airplanes and helicopters are significant sources of synthetic chemical contamination primarily through the use of aviation fuels, lubricants, and de-icing agents.	Aviation & Aerospace	PubChem
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	PubChem
CEDs000688	Glass Coatings?Glass coatings are synthetic chemical formulations applied to glass surfaces to enhance properties such as durability, UV resistance, and aesthetic appeal.	Building & Construction	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000727	Printing Machines Or Presses?Printing machines or presses commonly utilize synthetic chemicals such as inks, solvents, and cleaning agents.	Paper, pulp & fiber products	PubChem
CEDs000735	Explosives?Explosives are chemical compounds or mixtures designed to undergo rapid decomposition, releasing energy in the form of gas and heat.	Defense & military infrastructure	PubChem
CEDs000741	Pigment Pastes?Pigment pastes are concentrated dispersions of pigments used to impart color and properties to materials.	Paper, pulp & fiber products	PubChem

Pathways

2 pathwaysPathway Source: PathBank

Dihydroergotamine Mechanism of Action Action Pathway

Dihydroergotamine Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	Prediction Confidence Score 0.792 Applicability Domain 1.0 Statistical Significance 2.00e-05 Supporting Reference Compounds 823 E-value 0.155698
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	Prediction Confidence Score 0.792 Applicability Domain 1.0 Statistical Significance 8.00e-05 Supporting Reference Compounds 861 E-value 0.622794
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	Prediction Confidence Score 0.792 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 955 E-value 0.0778492
Click to view 3D structure	5-hydroxytryptamine receptor 6	P50406	Humans	Predicted (SEA)	Prediction Confidence Score 0.792 Applicability Domain 1.0 Statistical Significance 2.00e-05 Supporting Reference Compounds 536 E-value 0.155698
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	Prediction Confidence Score 0.792 Applicability Domain 1.0 Statistical Significance 1.00e-04 Supporting Reference Compounds 1103 E-value 0.778492
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Predicted (SEA)	Prediction Confidence Score 0.792 Applicability Domain 1.0 Statistical Significance 4.00e-05 Supporting Reference Compounds 340 E-value 0.311397
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	Prediction Confidence Score 0.792 Applicability Domain 1.0 Statistical Significance 4.00e-05 Supporting Reference Compounds 487 E-value 0.311397
Click to view 3D structure	Alpha-2C adrenergic receptor	P18825	Humans	Predicted (SEA)	Prediction Confidence Score 0.792 Applicability Domain 1.0 Statistical Significance 4.00e-05 Supporting Reference Compounds 386 E-value 0.311397
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	Prediction Confidence Score 0.693 Applicability Domain 1.0 Statistical Significance 2.30e-04 Supporting Reference Compounds 1538 E-value 1.79053
Click to view 3D structure	D(1A) dopamine receptor	P21728	Humans	Predicted (SEA)	Prediction Confidence Score 0.693 Applicability Domain 1.0 Statistical Significance 1.60e-04 Supporting Reference Compounds 425 E-value 1.24559
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P19327	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.693 Applicability Domain 1.0 Statistical Significance 3.60e-04 Supporting Reference Compounds 541 E-value 2.80257
Click to view 3D structure	5-hydroxytryptamine receptor 1B	P28564	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.693 Applicability Domain 1.0 Statistical Significance 3.00e-05 Supporting Reference Compounds 154 E-value 0.233548
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	Prediction Confidence Score 0.693 Applicability Domain 1.0 Statistical Significance 1.70e-04 Supporting Reference Compounds 686 E-value 1.32344
Click to view 3D structure	Alpha-1A adrenergic receptor	P43140	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.693 Applicability Domain 1.0 Statistical Significance 6.00e-05 Supporting Reference Compounds 208 E-value 0.467095
Click to view 3D structure	Alpha-1D adrenergic receptor	P25100	Humans	Predicted (SEA)	Prediction Confidence Score 0.693 Applicability Domain 1.0 Statistical Significance 5.00e-05 Supporting Reference Compounds 258 E-value 0.389246
Click to view 3D structure	Alpha-1B adrenergic receptor	P15823	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.693 Applicability Domain 1.0 Statistical Significance 4.00e-05 Supporting Reference Compounds 130 E-value 0.311397
Click to view 3D structure	5-hydroxytryptamine receptor 4	O70528	Cavia porcellus	Predicted (SEA)	Prediction Confidence Score 0.606 Applicability Domain 1.0 Statistical Significance 1.20e-04 Supporting Reference Compounds 94 E-value 0.934191
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	Prediction Confidence Score 0.575 Applicability Domain 0.953 Statistical Significance 0.0035 Supporting Reference Compounds 527 E-value 27.6365
Click to view 3D structure	5-hydroxytryptamine receptor 1B	P28222	Humans	Predicted (SEA)	Prediction Confidence Score 0.525 Applicability Domain 0.953 Statistical Significance 9.00e-04 Supporting Reference Compounds 337 E-value 7.00643
Click to view 3D structure	5-hydroxytryptamine receptor 5A	P47898	Humans	Predicted (SEA)	Prediction Confidence Score 0.524 Applicability Domain 0.953 Statistical Significance 3.40e-04 Supporting Reference Compounds 225 E-value 2.64687
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	Prediction Confidence Score 0.497 Applicability Domain 0.953 Statistical Significance 0.0064 Supporting Reference Compounds 953 E-value 50.057
Click to view 3D structure	Beta-2 adrenergic receptor	P07550	Humans	Predicted (SEA)	Prediction Confidence Score 0.49 Applicability Domain 0.953 Statistical Significance 9.00e-04 Supporting Reference Compounds 258 E-value 7.00643
Click to view 3D structure	5-hydroxytryptamine receptor 7	P34969	Humans	Predicted (SEA)	Prediction Confidence Score 0.487 Applicability Domain 0.953 Statistical Significance 0.0035 Supporting Reference Compounds 565 E-value 27.4808
Click to view 3D structure	D(4) dopamine receptor	P21917	Humans	Predicted (SEA)	Prediction Confidence Score 0.462 Applicability Domain 0.953 Statistical Significance 0.0052 Supporting Reference Compounds 524 E-value 40.793
Click to view 3D structure	Alpha-1A adrenergic receptor	P35348	Humans	Predicted (SEA)	Prediction Confidence Score 0.441 Applicability Domain 0.953 Statistical Significance 0.0046 Supporting Reference Compounds 376 E-value 35.6549
Click to view 3D structure	5-hydroxytryptamine receptor 1D	P28221	Humans	Known	Dihydroergotamine acts as an agonist at the 5-HT receptors. It is believed to alleviate migraines by either 1) activating 5-HT receptors located on intracranial blood vessels, including those on arterio-venous anastomoses, leads to vasoconstriction or 2) activating 5-HT receptors on sensory nerve endings of the trigeminal system resulting in the inhibition of pro-inflammatory neuropeptide release. (A365, A943, A944, A945, A946, A947, A2943)
Click to view 3D structure	5-hydroxytryptamine receptor 1B	P28222	Humans	Known	Dihydroergotamine acts as an agonist at the 5-HT receptors. It is believed to alleviate migraines by either 1) activating 5-HT receptors located on intracranial blood vessels, including those on arterio-venous anastomoses, leads to vasoconstriction or 2) activating 5-HT receptors on sensory nerve endings of the trigeminal system resulting in the inhibition of pro-inflammatory neuropeptide release. (A948, A949, A950, A951, A952, A2943)
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Known	Dihydroergotamine acts as an agonist at the 5-HT receptors. It is believed to alleviate migraines by either 1) activating 5-HT receptors located on intracranial blood vessels, including those on arterio-venous anastomoses, leads to vasoconstriction or 2) activating 5-HT receptors on sensory nerve endings of the trigeminal system resulting in the inhibition of pro-inflammatory neuropeptide release. (A365, A2945)
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Known	Dihydroergotamine acts as an agonist at the 5-HT receptors. It is believed to alleviate migraines by either 1) activating 5-HT receptors located on intracranial blood vessels, including those on arterio-venous anastomoses, leads to vasoconstriction or 2) activating 5-HT receptors on sensory nerve endings of the trigeminal system resulting in the inhibition of pro-inflammatory neuropeptide release. (A2943)
Click to view 3D structure	5-hydroxytryptamine receptor 1F	P30939	Humans	Known	Dihydroergotamine acts as an agonist at the 5-HT receptors. It is believed to alleviate migraines by either 1) activating 5-HT receptors located on intracranial blood vessels, including those on arterio-venous anastomoses, leads to vasoconstriction or 2) activating 5-HT receptors on sensory nerve endings of the trigeminal system resulting in the inhibition of pro-inflammatory neuropeptide release. (A2943)
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Known	Dihydroergotamine acts as an agonist at the 5-HT receptors. It is believed to alleviate migraines by either 1) activating 5-HT receptors located on intracranial blood vessels, including those on arterio-venous anastomoses, leads to vasoconstriction or 2) activating 5-HT receptors on sensory nerve endings of the trigeminal system resulting in the inhibition of pro-inflammatory neuropeptide release. (A2944)
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Known	Dihydroergotamine acts as an agonist at the 5-HT receptors. It is believed to alleviate migraines by either 1) activating 5-HT receptors located on intracranial blood vessels, including those on arterio-venous anastomoses, leads to vasoconstriction or 2) activating 5-HT receptors on sensory nerve endings of the trigeminal system resulting in the inhibition of pro-inflammatory neuropeptide release. (A2944)
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Known	Not Available
Click to view 3D structure	Multidrug and toxin extrusion protein 1	Q96FL8	Humans	Known	Not Available
Click to view 3D structure	Multidrug and toxin extrusion protein 2	Q86VL8	Humans	Known	Not Available
Click to view 3D structure	Solute carrier family 22 member 2	O15244	Humans	Known	Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00320

HMDB ID

HMDB0014465

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001724

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Link

General References

Richard JL: Some major mycotoxins and their mycotoxicoses--an overview. Int J Food Microbiol. 2007 Oct 20;119(1-2):3-10. Epub 2007 Jul 31. [PubMed: 17719115]
Mantegani S, Brambilla E, Varasi M: Ergoline derivatives: receptor affinity and selectivity. Farmaco. 1999 May 30;54(5):288-96. [PubMed: 10418123]
Schiff PL: Ergot and its alkaloids. Am J Pharm Educ. 2006 Oct 15;70(5):98. [PubMed: 17149427]
Kvernmo T, Hartter S, Burger E: A review of the receptor-binding and pharmacokinetic properties of dopamine agonists. Clin Ther. 2006 Aug;28(8):1065-78. [PubMed: 16982285]
Saper JR, Silberstein S: Pharmacology of dihydroergotamine and evidence for efficacy and safety in migraine. Headache. 2006 Nov;46 Suppl 4:S171-81. [PubMed: 17078849]
Silberstein SD: The pharmacology of ergotamine and dihydroergotamine. Headache. 1997;37 Suppl 1:S15-25. [PubMed: 9009470]
Drugs.com - http://www.drugs.com/cons/Dihydroergotamine.html
Wikipedia. Ergoline. Last Updated 2 April 2010. - http://en.wikipedia.org/wiki/Ergoline
Wikipedia. Ergotism. Last Updated 6 April 2010. - http://en.wikipedia.org/wiki/Ergotism
Van den Enden, E. (2004). Illustrated Lecture Notes on Tropical Medicine. - http://www.itg.be/evde/
Wikipedia. Dihydroergotamine. Last Updated 3 April 2010. - http://en.wikipedia.org/wiki/Dihydroergotamine
RxList: The Internet Drug Index (2010). D.H.E. 45 (Dihydroergotamine). - http://www.rxlist.com/dhe-45-drug.htm

Dihydroergotamine (CED0005910)

Structure for CHEM002169: Dihydroergotamine

Structure