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Chemistry

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Also known as: 11032-41-0, 6190-39-2, Dihydroergotamine methanesulfonate salt, (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,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carboxamide;methanesulfonic acid, Smr001230668, Prestwick_746
Molecular Formula
C34H41N5O8S
Molecular Weight
679.8  g/mol
InChI Key
ADYPXRFPBQGGAH-WVVAGBSPSA-N

Dihydroergotamine Mesylate
A mixture of three different hydrogenated derivatives of ERGOTAMINE: DIHYDROERGOCORNINE; DIHYDROERGOCRISTINE; and DIHYDROERGOCRYPTINE. Dihydroergotoxine has been proposed to be a neuroprotective agent and a nootropic agent. The mechanism of its therapeutic actions is not clear, but it can act as an alpha-adrenergic antagonist and a dopamine agonist. The methanesulfonate salts of this mixture of alkaloids are called ERGOLOID MESYLATES.
1 2D Structure

Dihydroergotamine Mesylate

2 Identification
2.1 Computed Descriptors
2.1.1 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,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide;methanesulfonic acid
2.1.2 InChI
InChI=1S/C33H37N5O5.CH4O3S/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;1-5(2,3)4/h3-6,8-11,17,21,23,25-27,34,42H,7,12-16,18H2,1-2H3,(H,35,39);1H3,(H,2,3,4)/t21-,23?,25-,26+,27+,32-,33+;/m1./s1
2.1.3 InChI Key
ADYPXRFPBQGGAH-WVVAGBSPSA-N
2.1.4 Canonical SMILES
CC1(C(=O)N2C(C(=O)N3CCCC3C2(O1)O)CC4=CC=CC=C4)NC(=O)C5CC6C(CC7=CNC8=CC=CC6=C78)N(C5)C.CS(=O)(=O)O
2.1.5 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]5CC6[C@@H](CC7=CNC8=CC=CC6=C78)N(C5)C.CS(=O)(=O)O
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Alkaloids, Hydrogenated Ergot

2. Co-dergocrine

3. Dihydroergotoxin

4. Ergot Alkaloids, Hydrogenated

5. Hydrogenated Ergot Alkaloids

2.2.2 Depositor-Supplied Synonyms

1. 11032-41-0

2. 6190-39-2

3. Dihydroergotamine Methanesulfonate Salt

4. (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,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carboxamide;methanesulfonic Acid

5. Smr001230668

6. Prestwick_746

7. Schembl40844

8. Mls002153175

9. Mls002207048

10. Chembl1396675

11. Hms2231h03

12. Hms3886k22

13. Dihydroergotamine For Peak Identification

14. D2633

15. Dihydroergotamine Methanesulfonate Salt, Powder

16. Q16633838

17. Z1544404034

18. Dihydroergotamine Mesilate, European Pharmacopoeia (ep) Reference Standard

19. Dihydroergotamine For Peak Identification, European Pharmacopoeia (ep) Reference Standard

20. Dihydroergotamine Mesylate, United States Pharmacopeia (usp) Reference Standard

21. (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(15),9,12(16),13-tetraene-4-carboxamide; Methanesulfonic Acid

22. (6ar,9r)-n-((2r,5s,10as,10bs)-5-benzyl-10b-hydroxy-2-methyl-3,6-dioxooctahydro-2h-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

23. (6ar,9r)-n-((2r,5s,10as,10bs)-5-benzyl-10b-hydroxy-2-methyl-3,6-dioxooctahydro-2h-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide Methanesulfonate

24. (6ar,9r)-n-((2r,5s,10as,10bs)-5-benzyl-10b-hydroxy-2-methyl-3,6-dioxooctahydro-8h-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide Methanesulfonate

25. 910882-41-6

2.3 Create Date
2006-04-14
3 Chemical and Physical Properties
Molecular Weight 679.8 g/mol
Molecular Formula C34H41N5O8S
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count9
Rotatable Bond Count4
Exact Mass679.26758446 g/mol
Monoisotopic Mass679.26758446 g/mol
Topological Polar Surface Area181 Ų
Heavy Atom Count48
Formal Charge0
Complexity1260
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameDihydroergotamine mesylate
Active IngredientDihydroergotamine mesylate
Dosage FormInjectable
RouteInjection
Strength1mg/ml
Market StatusPrescription
CompanyPaddock; Bedford Labs

2 of 2  
Drug NameDihydroergotamine mesylate
Active IngredientDihydroergotamine mesylate
Dosage FormInjectable
RouteInjection
Strength1mg/ml
Market StatusPrescription
CompanyPaddock; Bedford Labs

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Adrenergic alpha-Antagonists

Drugs that bind to but do not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists. Adrenergic alpha-antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma. (See all compounds classified as Adrenergic alpha-Antagonists.)


Dopamine Agonists

Drugs that bind to and activate dopamine receptors. (See all compounds classified as Dopamine Agonists.)


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20-Dec-2023
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