Structure via PubChem · Public domain (PubChem)
ergotamine
Sign in to saveAlso known as 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, (5'α)-12'-hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'α-(phenylmethyl)ergotaman-3',6',18-trione
Ergotamine, sold under the brand name Ergomar among others, is an ergopeptine and part of the ergot family of alkaloids; it is structurally and biochemically closely related to ergoline. It is structurally similar to several neurotransmitters, and it acts as a vasoconstrictor. It is used for acute migraines, sometimes with caffeine as the combination ergotamine/caffeine.
Key facts
- Drug.StdInChI
- 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
- Drug.StdInChIKey
- XCGSFFUVFURLIX-VFGNJEKYSA-N
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 443732840
- Drug.image
- Ergotamine-skeletal.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200px
- Drug.image2
- Ergotamine ball-and-stick.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 250px
- Drug.tradename
- Ergomar, others
- Drug.DailyMedID
- Ergotamine
- Drug.pregnancy_AU
- C
- Drug.pregnancy_category
- US: Contraindicated
- Drug.routes_of_administration
- Oral
- Drug.ATC_prefix
- N02
- Drug.ATC_suffix
- CA02
via Wikipedia infobox
Chemical data
- Formula
- C33H35N5O5
- Molecular weight
- 581.7 g/mol
- 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
- 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
- InChIKey
- XCGSFFUVFURLIX-VFGNJEKYSA-N
- XLogP
- 2
- Polar surface area
- 118 Ų
- H-bond donors
- 3
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Research
13,523 papers- Ergotamine enhances circadian amplitude and diurnally mitigates nitroglycerin-induced mechanical hypersensitivity.The journal of headache and pain · 2025
- Ergotamine and nicergoline - facts and myths.Pharmacological reports : PR · 2015
- Ergotamine and dihydroergotamine: a review.Current pain and headache reports · 2003
- Ergotamine dependency--a review.Headache · 1987
- Ergotamine and dihydroergotamine: history, pharmacology, and efficacy.Headache · 2003
via PubMed
Wikidata facts
- Mass
- 581.264
Show 6 more facts
- chemical formula
- C₃₃H₃₅N₅O₅
- 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
- World Health Organisation international non-proprietary name
- ergotamine
- Commons category
- Ergotamine
- defined daily dose
- 4
via Wikidata · CC0
~6 min read
Article
15 sectionsContents
- Medical uses
- Available forms
- Contraindications
- Side effects
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Natural occurrence
- Biosynthesis
- Society and culture
- Legal status
- United States
- See also
- References
- External links
Ergotamine, sold under the brand name Ergomar among others, is an ergopeptine and part of the ergot family of alkaloids; it is structurally and biochemically closely related to ergoline. It is structurally similar to several neurotransmitters, and it acts as a vasoconstrictor. It is used for acute migraines, sometimes with caffeine as the combination ergotamine/caffeine.
The drug is a non-selective modulator or agonist of serotonin receptors and other receptors. It is peripherally selective and crosses into the brain in minimal amounts.