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Analgesics and anti-inflammatories

Ergotamine

Also known as Ergotamin, Ergonsvine, Ergotamina

CAS 113-15-5Formula C33H35N5O5Molar mass 581.67 g/molEC 204-023-9
GHS signal word: Danger. Pictograms: Acute toxicity (severe), Harmful or irritant, Serious health hazard Controlled, licensed buyers only Drug substance
Request as a licensed buyer Safety data
Ergotamine chemical structure, C33H35N5O5, CAS 113-15-5
2D chemical structure

Key facts

What buyers check first

All properties
Appearance
Needles from alcohol, prisms from benzene, plates from acetone
Melting point
213 °C
Solubility
Almost insoluble in water
HS code
293962
Category
Analgesics and anti-inflammatories

What is Ergotamine?

Plain description, key identifiers and synonyms

Ergotamine is a peptide ergot alkaloid that is dihydroergotamine in which a double bond replaces the single bond between positions 9 and 10. It has a role as a mycotoxin, a non-narcotic analgesic, an alpha-adrenergic agonist, a serotonergic agonist, an oxytocic and a vasoconstrictor agent. It is a conjugate base of an ergotamine(1+).

Identifiers

Registry numbers, names and line notations, tap to copy

IUPAC name
(6aR,9R)-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]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
CAS number
113-15-5 CAS number cross-checkedOther or deprecated CAS: 1080650-16-3
EC number
204-023-9
Molecular formula
C33H35N5O5
UNII
PR834Q503T
MDL number
MFCD00864261
InChIKey
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
CN1CC(C(=O)NC2(C)OC3(O)C4CCCN4C(=O)C(Cc4ccccc4)N3C2=O)C=C2c3cccc4[nH]cc(c34)CC21
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

Synonyms

  • Ergotamin
  • Ergonsvine
  • Ergotamina
  • ergotaminum
  • 12'-Hydroxy-2'-methyl-5'alpha-(phenylmethyl)ergotaman-3',6',18-trione
  • (5'alpha)-12'-Hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione
  • Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'-alpha)-
  • Ergo Kranit
  • Mono, Ergodryl
  • Gynergen
  • Ergomar
  • Ergotamine (INN)
  • 5'alpha-benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxoergotaman
  • ERM
  • Ergotamin, ergotaminum
  • Ergotamine tartrate, Avetol, Cornutamin, Ergam, Ergotartrate
  • Ergotamine dried down 100 microg/mL
  • Codergocrine mesilate impurity c
  • (5'alpha)-5'-benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxoergotaman
  • (5''alpha)-12''-hydroxy-2''-methyl-5''-(phenylmethyl)ergotoman-3'',6'',18-trione
  • (5''alpha)-5''-benzyl-12''-hydroxy-2''-methyl-3'',6'',18-trioxoergotaman
  • (5alpha,5'beta)-5'-benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxoergotaman
  • 12''-hydroxy-2''-methyl-5''alpha-(phenylmethyl)ergotaman-3'',6'',18-trione
  • N-[(2R,5S,10aS,10bS)-5-benzyl-10b-hydroxy-2-methyl-3,6-dioxo-8,9,10,10a-tetrahydro-5H-oxazolo[[?]]pyrrolo[[?]]pyrazin-2-yl]-methyl-[?]carboxamide

Physical and chemical properties

Measured values and descriptors computed from the structure

Physical and chemical properties

Measured values, check the supplier specification for your grade

Appearance
Needles from alcohol, prisms from benzene, plates from acetoneexp.
Melting point
213 °Cexp.
Solubility
Almost insoluble in waterexp.

Values vary by grade. Ask suppliers for the COA or TDS of the batch you buy.

Computed descriptors

Calculated from the structure, useful for screening and formulation

Molecular weight
581.67 g/molcalc.
Exact mass
581.2638 Dacalc.
LogP (octanol/water)
1.99calc.
Topological polar surface area
118.2 Ųcalc.
Hydrogen bond donors
3calc.
Hydrogen bond acceptors
6calc.
Rotatable bonds
4calc.
Heavy atoms
43calc.
Rings
8calc.
Aromatic rings
3calc.
Fraction sp3 carbons
0.42calc.
Formal charge
0calc.
Stereocentres
6calc.
Lipinski rule of five
Passes (1 violation)calc.

Calculated for screening. Confirm critical figures with the supplier.

Murcko scaffold

The ring system that remains when every side chain is removed

Murcko scaffold of this chemical, O=C(NC1OC2C3CCCN3C(=O)C(Cc3ccccc3)N2C1=O)C1C=C2c3cccc4[nH]cc(c34)CC2NC1

O=C(NC1OC2C3CCCN3C(=O)C(Cc3ccccc3)N2C1=O)C1C=C2c3cccc4[nH]cc(c34)CC2NC1

8 rings, 40 atoms.

28 other chemicals share this scaffold

Safety and hazards

GHS classification summary, not a safety data sheet

GHS signal word
Danger
GHS06: Acute toxicity (severe)
Acute toxicity (severe)
GHS07: Harmful or irritant
Harmful or irritant
GHS08: Serious health hazard
Serious health hazard

Hazard statements

  • H301Toxic if swallowed.
  • H302Harmful if swallowed.
  • H311Toxic in contact with skin.
  • H312Harmful in contact with skin.
  • H330Fatal if inhaled.
  • H331Toxic if inhaled.
  • H332Harmful if inhaled.
  • H361Suspected of damaging fertility or the unborn child.
Precautionary statements (24)
  • P203Obtain, read and follow all safety instructions before use.
  • P260Do not breathe dust, fume, gas, mist, vapours or spray.
  • P261Avoid breathing dust, fume, gas, mist, vapours or spray.
  • P262Do not get in eyes, on skin, or on clothing.
  • P264Wash skin thoroughly after handling.
  • P270Do not eat, drink or smoke when using this product.
  • P271Use only outdoors or in a well-ventilated area.
  • P280Wear protective gloves, protective clothing, eye protection and face protection.
  • P284In case of inadequate ventilation wear respiratory protection.
  • P301 + P316If swallowed: Get emergency medical help immediately.
  • P301 + P317If swallowed: Get medical help.
  • P302 + P352If on skin: Wash with plenty of water.
  • P304 + P340If inhaled: Remove person to fresh air and keep comfortable for breathing.
  • P316Get emergency medical help immediately.
  • P317Get medical help.
  • P318If exposed or concerned, get medical advice.
  • P320Specific treatment is urgent (see supplemental first aid instructions on the label).
  • P321Specific treatment (see supplemental first aid instructions on the label).
  • P330Rinse mouth.
  • P361 + P364Take off immediately all contaminated clothing. And wash it before reuse.
  • P362 + P364Take off contaminated clothing. And wash it before reuse.
  • P403 + P233Store in a well-ventilated place. Keep container tightly closed.
  • P405Store locked up.
  • P501Dispose of contents and container in accordance with local regulations.

GHS classification summary, not a safety data sheet (SDS). Classifications can differ by supplier, grade and concentration. Always check the supplier's SDS.

Full safety data and first aid

Ergotamine suppliers

Controlled substance, listings of documented suppliers only, in the documented ranking

Drug precursor

Ergotamine is controlled. Only documented suppliers can list it, and buyers must upload a valid licence with their request. Every request is reviewed before suppliers see it.

Licensed buyers only, every enquiry is reviewed by our compliance team.

Reference: UN Convention against Illicit Traffic 1988 Table I, India NDPS controlled substance, HS 2022 subheading 2939.62 (ergotamine)

Our policy on controlled substances
No documented supplier lists it yet

Licensed buyers can post a request for Ergotamine with their licence. Our compliance team reviews it before suppliers see it.

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Ergotamine price

Indicative price range per kg from live supplier offers

No published prices right now

Suppliers quote this chemical on request. Send one free request and compare quotes side by side.

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Uses and applications

What the substance is used for, by industry and function

Oxytocics, Vasoconstrictor Agents, Serotonin Receptor Agonists, Analgesics, Non-Narcotic, Adrenergic alpha-1 Receptor Agonists.

Veterinary medication:.

Use classes: Pharmaceuticals.

Pharmacological actions

  • Adrenergic alpha-1 Receptor Agonists
  • Analgesics, Non-Narcotic
  • Oxytocics
  • Serotonin Receptor Agonists
  • Vasoconstrictor Agents

Roles

  • adrenergic agent
  • adrenergic agonist
  • alpha-adrenergic agonist
  • alpha-adrenergic drug
  • analgesic
  • cardiovascular drug
  • eukaryotic metabolite
  • fungal metabolite
  • metabolite
  • mycotoxin
  • neurotransmitter agent
  • non-narcotic analgesic
  • oxytocic
  • pharmaceutical
  • poison
  • serotonergic agonist
  • serotonergic drug
  • toxin
  • vasoconstrictor agent

Pharmacology

Ergotamine is an Ergotamine Derivative.

How it is made

Commercial production involves generation parasitically on rye in the field or production in culture because a commercially useful synthesis is unavailable. The common technique today is to grow the fungus in submerged culture. Claviceps paspali (Stevens and Hall) is said to be more productive than C. purpurea (Fries). In this way, ergotamine and ergonovine are produced. Ergotamine is obtained from crude extract by formation of an aluminum complex. Destruction of the aluminum complex with ammonia then permits hydrocarbon extraction of the alkaloid. The alkaloid is subsequently both isolated and used as its tartrate salt.

Regulatory status

Inventories, regulations and trade controls that list this substance

Drug precursor

Ergotamine is controlled. Only documented suppliers can list it, and buyers must upload a valid licence with their request. Every request is reviewed before suppliers see it.

Licensed buyers only, every enquiry is reviewed by our compliance team.

Reference: UN Convention against Illicit Traffic 1988 Table I, India NDPS controlled substance, HS 2022 subheading 2939.62 (ergotamine)

Our policy on controlled substances

Controls

  • US DEA controlled substance or listed chemical
  • Drug precursor (UN 1988 Convention)

Health and food

  • Active ingredient in FDA approved drug labels

HS code and trade data

Customs classification and reported world trade statistics

Global trade

World import and export statistics for the HS code Ergotamine is traded under.

HS 2939.62Exact HS code

Ergotamine (INN) and its salts

World exports in 2024
$6.41M
+19.5% vs 2023, imports $6.23M
2019 to 2024
Top exporters
  1. Czech Republic63.7%
  2. Switzerland * partner reported15.6%
  3. Germany13.0%
Top importers
  1. Germany16.0%
  2. Switzerland * partner reported14.3%
  3. Ecuador * partner reported14.0%

* Partner reported figures, a lower bound.

Reported customs values in USD, not prices.Full trade data

The HS code shown for Ergotamine is indicative (it was matched by name in the HS nomenclature). Confirm the classification with your customs broker before shipping.

Frequently asked questions

Quick answers about Ergotamine, based on the data on this page

What is Ergotamine?

Ergotamine is a peptide ergot alkaloid that is dihydroergotamine in which a double bond replaces the single bond between positions 9 and 10. It has a role as a mycotoxin, a non-narcotic analgesic, an alpha-adrenergic agonist, a serotonergic agonist, an oxytocic and a vasoconstrictor agent.

What is the CAS number of Ergotamine?

The CAS registry number of Ergotamine is 113-15-5. Other or deprecated CAS numbers: 1080650-16-3.

What is the molecular formula and weight of Ergotamine?

The molecular formula of Ergotamine is C33H35N5O5 and its molar mass is 581.67 g/mol.

What is Ergotamine used for?

Oxytocics, Vasoconstrictor Agents, Serotonin Receptor Agonists, Analgesics, Non-Narcotic, Adrenergic alpha-1 Receptor Agonists. Veterinary medication:. Use classes: Pharmaceuticals.

Is Ergotamine hazardous?

Ergotamine carries the GHS signal word "Danger". Main hazards: toxic if swallowed, harmful if swallowed, toxic in contact with skin. This summary is not an SDS, always read the supplier safety data sheet.

What is the HS code of Ergotamine?

Ergotamine is usually classified under HS code 293962 (Ergotamine (INN) and its salts). This is indicative, confirm it with your customs broker before shipping.

Can I buy Ergotamine on CompoundList?

Ergotamine is a controlled substance. Only documented suppliers can list it, and buyers must upload a valid licence with their request. Every request is reviewed by our compliance team before suppliers see it.

Guides for buyers

Practical guides that help when you source, ship or handle Ergotamine

Request as a licensed buyer

Upload your licence with the request. Our compliance team reviews it before the documented suppliers see it.
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Data last updated 7 Oct 2026. Details may have changed, please confirm them with the supplier. Report an error on this page
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