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Dihydroergotamine Mesylate

Dihydroergotamine Mesylate

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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

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 Formula	C₃₄H₄₁N₅O₈S
Molecular Weight	679.8 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	4
Exact Mass	679.26758446 g/mol
Monoisotopic Mass	679.26758446 g/mol
Topological Polar Surface Area	181 Å²
Heavy Atom Count	48
Formal Charge	0
Complexity	1260
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Dihydroergotamine mesylate
Active Ingredient	Dihydroergotamine mesylate
Dosage Form	Injectable
Route	Injection
Strength	1mg/ml
Market Status	Prescription
Company	Paddock; Bedford Labs

2 of 2
Drug Name	Dihydroergotamine mesylate
Active Ingredient	Dihydroergotamine mesylate
Dosage Form	Injectable
Route	Injection
Strength	1mg/ml
Market Status	Prescription
Company	Paddock; 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.)