Ergotamine (CED0004108)

Record Information

Version

1.0

Creation Date

2009-07-03 21:06:25 UTC

Update Date

2026-05-14 16:46:20 UTC

Accession Number

CHEM002048

Identification

Common Name

Ergotamine

Class

Small Molecule

Description

Ergotamine belongs to the lysergic acids and derivatives, a subclass of ergoline and derivatives within the organic compounds. With an average molecular weight of 581.66 g/mol, Ergotamine is a heavy molecule. This exogenous compound has the formula C33H35N5O5 and exists as a solid at room temperature. It is utilized as a non-narcotic analgesic, a vasoconstrictor agent, a serotonergic agonist, and an alpha-adrenergic agonist. Exposure routes include oral, sublingual, rectal, inhalation, and touch. It is found in 25 recorded sources across various sectors, including healthcare, pharmaceuticals and veterinary products (analgesics, medical devices), food, food processing and cookware (food preservation, food packaging), energy, oil and gas (lubricants), textiles, leather and furnishings (carpets and rugs, synthetic textiles), household cleaning and consumer products (tobacco smoke filters, tobacco product cases, perfumes within detergents and soaps, non electric simulated smoking devices, cigar cigarettes), and electrical and electronic equipment (batteries, printed circuit boards, wires and cables, capacitors, cell phones, and 6 more). Ergotamine targets 17 proteins, acting as an agonist at several receptors. It acts as an agonist at alpha-adrenergic receptors, including the alpha-1A (ADRA1A), alpha-1B (ADRA1B), alpha-2A (ADRA2A), and alpha-2B (ADRA2B) adrenergic receptors, which causes vasoconstriction. It also acts as an agonist at the 5-HT1D (HTR1D) and 5-HT1B (HTR1B) receptors located on intracranial blood vessels, including those on arterio-venous anastomoses, leading to vasoconstriction, and activates these receptors on sensory nerve endings of the trigeminal system to inhibit pro-inflammatory neuropeptide release. Additionally, it acts as an agonist at 5-HT2 receptors (HTR2A, HTR2B, HTR2C), causing vasoconstriction, and at the D(2) dopamine receptor (DRD2). Other protein targets include the D(1A) dopamine receptor (DRD1), 5-hydroxytryptamine receptor 1A (HTR1A), 5-hydroxytryptamine receptor 1F (HTR1F), and the sodium-dependent noradrenaline transporter (SLC6A2).

Contaminant Type

Adrenergic alpha-Agonist
Amide
Amine
Analgesic, Non-Narcotic
Drug
Ether
Fungal Toxin
Human Neurotoxin
Metabolite
Mycotoxin
Natural Compound
Organic Compound
PFAS
Sympatholytic
Vasoconstrictor Agent

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(5'alpha)-12'-Hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione	ChEBI
12'-Hydroxy-2'-methyl-5'alpha-(phenylmethyl)ergotaman-3',6',18-trione	ChEBI
Ergotamin	ChEBI
Ergotamina	ChEBI
Ergotaminum	ChEBI
Gynergen	ChEBI
(5'a)-12'-Hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione	Generator
(5'Α)-12'-hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione	Generator
12'-Hydroxy-2'-methyl-5'a-(phenylmethyl)ergotaman-3',6',18-trione	Generator
12'-Hydroxy-2'-methyl-5'α-(phenylmethyl)ergotaman-3',6',18-trione	Generator
Cornutamine	HMDB
Ergotaminine	HMDB
Lingraine	HMDB
Tartrate, ergotamine	HMDB
ErgoKranit	HMDB
Ergo-kranit	HMDB
Ergotamine tartrate (2:1)	HMDB
mono, Ergodryl	HMDB
Pfizer brand OF ergotamine tartrate	HMDB
Ergo sanol	HMDB
Ergo kranit	HMDB
Ergodryl mono	HMDB
Ergomar	HMDB
Ergostat	HMDB
Ergotamine tartrate	HMDB
Krewel brand OF ergotamine tartrate	HMDB
Lotus brand OF ergotamine tartrate	HMDB
Sanofi winthrop brand OF ergotamine tartrate	HMDB

Chemical Formula

C₃₃H₃₅N₅O₅

Average Molecular Mass

581.662 g/mol

Monoisotopic Mass

581.264 g/mol

CAS Registry Number

113-15-5

IUPAC Name

(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),2,9,12,14-pentaene-4-carboxamide

Traditional Name

ergomar

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)C4=C3)O[C@@]21O

InChI Identifier

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

InChI Key

XCGSFFUVFURLIX-VFGNJEKYSA-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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

peptide ergot alkaloid (CHEBI:64318 )

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

Ergomar® Sublingual Tablets are round, green tablets each containing 2 mg of ergotamine tartrate.

Experimental Properties

Property	Value
Melting Point	213.5 dec°C
Boiling Point	Not Available
Solubility	Slight

Predicted Properties

Property	Value	Source
Water Solubility	0.22 g/L	ALOGPS
logP	2.95	ALOGPS
logP	2.6	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.7	ChemAxon
pKa (Strongest Basic)	7.78	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	160.17 m³·mol⁻¹	ChemAxon
Polarizability	61.69 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	splash10-0gi0-6692120000-7fabddfa08a8dd219bc3	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0g4j-9281023000-06e454bbac7ea8189ead	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-0022090000-66faf61c3242915f91f8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0uyi-0091010000-98b25c5586801771014a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-4290000000-42f48d5180d5f2f5c20e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0019-0049160000-6be92986c4d5c2bd6dad	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0aor-2196220000-c51c3bf00ec927a5631b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0g5a-9810000000-7522033f4e775f417ffa	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0000090000-34b8023f9528c85e96bc	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0020190000-ec8f5848bc681f03dbe9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0090020000-c4d316e57df458ef5f72	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0000090000-7dfa0cf0a740c633816a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-2100390000-8129f2d9526dbde472d8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0fvi-9252430000-c9d112acb2b7bf8de124	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Ergoline alkaloids tend to act as a group, producing complex and variable effects of partial agonism or antagonism at adrenergic, dopaminergic, and serotonergic receptors. Variables relating to these effects are influenced by the agent, dosage, species, tissue, physiological, and endocrinological state, and experimental conditions. In particular, ergoline alkaloids have been shown to have the significant affinity towards the 5-HT1 and 5-HT2 serotonin receptors, D1 and D2 dopamine receptors, and alpha-adrenergic receptors. This can result in a number of different effects, including vasoconstriction, convulsions, and hallucinations. Ergometrine is also known to have a non-receptor specific oxytocic activity. Ergotamine acts on migraine by one of two proposed mechanisms: 1) activation of 5-HT1D receptors located on intracranial blood vessels, including those on arterio-venous anastomoses, leading to vasoconstriction, which correlates with the relief of migraine headache, and 2) activation of 5-HT1D receptors on sensory nerve endings of the trigeminal system, resulting in the inhibition of pro-inflammatory neuropeptide release. (4, 5, 6)

Carcinogenicity (IARC Classification)

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

Minimum Risk Level

Not Available

Symptoms

Signs of ergotamine overexposure include irritation, nausea, vomiting, headache, diarrhea, thirst, coldness of skin, pruritus, weak pulse, numbness, tingling of extremities, and confusion. 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. (1, 9, 10)

Treatment

Treatment consists of removal of the offending drug. Maintenance of adequate pulmonary ventilation, correction of hypotension, and control of convulsions and blood pressure are important considerations. Treatment of peripheral vasospasm should consist of warmth, but not heat, and protection of the ischemic limbs. Vasodilators may be beneficial but caution must be exercised to avoid aggravating an already existent hypotension. (9)

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
62.0	mg/kg	Not Available	Rat	LD50	Intravenous	experimental	T178
239.0	Log mg/kg	[130:430]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
7	Pesticides	Agriculture & land management	Not Available
10	Insecticides	Agriculture & land management	Not Available
120	Wires and cables	Electrical & Electronic Equipment	Not Available
121	Printed circuit boards	Electrical & Electronic Equipment	Not Available
125	Batteries	Electrical & Electronic Equipment	Not Available
130	Semiconductors	Electrical & Electronic Equipment	Not Available
138	Lubricants	Energy, oil & gas	Not Available
147	Food packaging	Food, food processing & cookware	Not Available
174	Lubricants	Industrial manufacturing & chemical processing	Not Available
234	Medical devices	Healthcare, pharmaceuticals & veterinary products	Not Available
370	Analgesics	Healthcare, pharmaceuticals & veterinary products	Not Available
451	Carpets and Rugs	Textiles, leather & furnishings	Not Available
454	Synthetic textiles	Textiles, leather & furnishings	Not Available
490		Personal care & cosmetics	Not Available
492	Cell phones	Electrical & Electronic Equipment	Not Available
493	Capacitors	Electrical & Electronic Equipment	Not Available
505	Amplifiers	Electrical & Electronic Equipment	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
516	Electric Hearing Aids	Electrical & Electronic Equipment	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
519	Electrodes	Electrical & Electronic Equipment	Not Available
545	Food Preservation	Food, food processing & cookware	Not Available
556	Cigar Cigarettes	Household cleaning & consumer products	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
561	Perfumes Within Detergents And Soaps	Household cleaning & consumer products	Not Available
567	Tobacco Product Cases	Household cleaning & consumer products	Not Available
569	Tobacco Smoke Filters	Household cleaning & consumer products	Not Available
579	Manufacture Of Iron Or Steel	Industrial manufacturing & chemical processing	Not Available
580	Manufacture Preparation Of Tobacco Products	Industrial manufacturing & chemical processing	Not Available
596	Acaricides	Agriculture & land management	Not Available
603	Nematocides	Agriculture & land management	Not Available
606	Plant Growth Regulators	Agriculture & land management	Not Available
611	Anti Perspirants Or Body Deoderants	Personal care & cosmetics	Not Available
613	Depilatories	Personal care & cosmetics	Not Available
614	Essential Oils Or Perfumes	Personal care & cosmetics	Not Available
615	Eye Makeup Products	Personal care & cosmetics	Not Available
617	Lip Care Products	Personal care & cosmetics	Not Available
618	Lip Makeup Products	Personal care & cosmetics	Not Available
632	Apparel	Textiles, leather & furnishings	Not Available
642	Footwear	Textiles, leather & furnishings	Not Available
650	Purses Luggage Hand Bags	Textiles, leather & furnishings	Not Available

Pathways

2 pathways

Ergotamine Mechanism of Action Action Pathway

Ergotamine 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)	0.544945
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	0.467095
Click to view 3D structure	5-hydroxytryptamine receptor 6	P50406	Humans	Predicted (SEA)	0.311397
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	2.02408
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	1.94623
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Predicted (SEA)	0.467095
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	0.467095
Click to view 3D structure	Alpha-2C adrenergic receptor	P18825	Humans	Predicted (SEA)	0.544945
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	1.16774
Click to view 3D structure	D(1A) dopamine receptor	P21728	Humans	Predicted (SEA)	0.467095
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P19327	Rattus norvegicus	Predicted (SEA)	1.71268
Click to view 3D structure	5-hydroxytryptamine receptor 1B	P28564	Rattus norvegicus	Predicted (SEA)	0.155698
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	0.389246
Click to view 3D structure	Alpha-1A adrenergic receptor	P43140	Rattus norvegicus	Predicted (SEA)	0.233548
Click to view 3D structure	Alpha-1D adrenergic receptor	P25100	Humans	Predicted (SEA)	0.311397
Click to view 3D structure	Alpha-1B adrenergic receptor	P15823	Rattus norvegicus	Predicted (SEA)	0.233548
Click to view 3D structure	5-hydroxytryptamine receptor 5A	P47898	Humans	Predicted (SEA)	1.16774
Click to view 3D structure	Beta-2 adrenergic receptor	P07550	Humans	Predicted (SEA)	1.63483
Click to view 3D structure	Beta-1 adrenergic receptor	P08588	Humans	Predicted (SEA)	2.25763
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	23.744
Click to view 3D structure	5-hydroxytryptamine receptor 1B	P28222	Humans	Predicted (SEA)	4.82665
Click to view 3D structure	5-hydroxytryptamine receptor 4	O70528	Cavia porcellus	Predicted (SEA)	2.49118
Click to view 3D structure	5-hydroxytryptamine receptor 7	P34969	Humans	Predicted (SEA)	13.4679
Click to view 3D structure	D(4) dopamine receptor	P21917	Humans	Predicted (SEA)	22.6541
Click to view 3D structure	5-hydroxytryptamine receptor 1D	P28221	Humans	Predicted (SEA)	9.10836
Click to view 3D structure	5-hydroxytryptamine receptor 1D	P28221	Humans	Known	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. (A946, A1500, A947, A1501, A1502)
Click to view 3D structure	5-hydroxytryptamine receptor 1B	P28222	Humans	Known	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. (A1503, A948, A1462, A1504)
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Known	Ergotamine acts as an agonist at 5-HT2 receptors, causing vasoconstriction. (A1505, A1506, A365)
Click to view 3D structure	Alpha-1A adrenergic receptor	P35348	Humans	Known	Ergotamine acts as an agonist at alpha-adrenergic receptors, causing vasoconstriction. (A358, A359, A1504)
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Known	Ergotamine acts as an agonist at 5-HT2 receptors, causing vasoconstriction. (A1505, A1506, A365)
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Known	Ergotamine acts as an agonist at 5-HT2 receptors, causing vasoconstriction. (A1505, A1506, A365)
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Known	Ergotamine acts as an agonist at alpha-adrenergic receptors, causing vasoconstriction. (A358, A359, A1504)
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Known	Ergotamine acts as an agonist at alpha-adrenergic receptors, causing vasoconstriction. (A358, A359, A1504)
Click to view 3D structure	Alpha-1B adrenergic receptor	P35368	Humans	Known	Ergotamine acts as an agonist at alpha-adrenergic receptors, causing vasoconstriction. (A1504)
Click to view 3D structure	Alpha-1D adrenergic receptor	P25100	Humans	Known	Ergotamine acts as an agonist at alpha-adrenergic receptors, causing vasoconstriction. (A1504)
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Known	Ergotamine acts as an agonist at D(2) dopamine receptors. (A1497, A1499)
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Known	Not Available
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Known	Not Available
Click to view 3D structure	5-hydroxytryptamine receptor 1F	P30939	Humans	Known	Not Available
Click to view 3D structure	Alpha-2C adrenergic receptor	P18825	Humans	Known	Ergotamine acts as an agonist at alpha-adrenergic receptors, causing vasoconstriction. (A1504)