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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.)

    API Reference Price

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    17-Feb-2021
    30-Jan-2024
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