ContaminantDB: Dihydroergotamine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (23)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:26:35 UTC

Update Date

2026-05-14 16:25:23 UTC

Accession Number

CHEM002169

Identification

Common Name

Dihydroergotamine

Class

Small Molecule

Description

Dihydroergotamine is only found in individuals that have used or taken this drug. It is a 9,10alpha-dihydro derivative of ergotamine. It is used as a vasoconstrictor, specifically for the therapy of migraine disorders. 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.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

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[7.3.0.0^{2,6}]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]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

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

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	1	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	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fr5-5891210000-f53c38352e2598f9007e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fdn-7491022000-6c73d0337e04ab2f6918	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Dihydroergotamine,1TMS,#1" TMS) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0022090000-bfd200952b03e8b137ff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0un9-0091010000-c5661ba02ab58100d046	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-4590000000-dc4a0cca36e4ae6c18c5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0019-0049160000-4fdc70b6d84db2eb175e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03xr-2196220000-3c3fcf127102792f663c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0g4j-9810000000-88f13186254d2bf07e89	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000090000-3abf973bfa14967f7f1d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0010290000-1037c6e147fa5f93e653	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0090010000-f5347f35594f87c4297f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000090000-10b01aae8e192c05edc6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-2100390000-475a2b73d09ae5f9c174	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0v03-9351430000-9c41d997e0687489c4ee	Spectrum

Toxicity Profile

Route of Exposure

Intravenous (7); Nasal (7). Interpatient variable and may be dependent on the administration technique

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.

Metabolism

Dihydroergotamine is metabolized in the liver, with metabolites predominantly excreted in the feces. (5) Route of Elimination: The major excretory route of dihydroergotamine is via the bile in the feces. Only 6%-7% of unchanged dihydroergotamine is excreted in the urine after intramuscular injection. Half Life: 9 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

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

Uses/Sources

Dihydroergotamine is a 9,10alpha-dihydro derivative of ergotamine. It is used as a vasoconstrictor, specifically for the therapy of migraine disorders. Ergoline alkaloids occurs in various species of vines of the Convolvulaceae (morning glory) family and in some species of lower fungi. (8, 11) For the acute treatment of migraine headaches with or without aura and the acute treatment of cluster headache episodes.

Minimum Risk Level

Not Available

Health Effects

Ingestion of ergoline alkaloids is known to cause the disease ergotism. Ergotism occurs in two forms, gangrenous and convulsive, likely depending on the different kinds and amounts of ergoline alkaloids present. (1, 12)

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)

Concentrations

Not Available

External Links

DrugBank ID

DB00320

HMDB ID

HMDB0014465

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID