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    Sparteine Sulfate

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    2D Structure
    Also known as: Sparteine sulfate, 299-39-8, Tocosimplex, (-)-sparteine (sulfate), Actospar, Depasan
    Molecular Formula
    C15H28N2O4S
    Molecular Weight
    332.5  g/mol
    InChI Key
    FCEHFCFHANDXMB-UHFFFAOYSA-N
    A quinolizidine alkaloid isolated from several FABACEAE including LUPINUS; SPARTIUM; and CYTISUS. It has been used as an oxytocic and an anti-arrhythmia agent. It has also been of interest as an indicator of CYP2D6 genotype.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecane;sulfuric acid
    2.1.2 InChI
    InChI=1S/C15H26N2.H2O4S/c1-3-7-16-11-13-9-12(14(16)5-1)10-17-8-4-2-6-15(13)17;1-5(2,3)4/h12-15H,1-11H2;(H2,1,2,3,4)
    2.1.3 InChI Key
    FCEHFCFHANDXMB-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1CCN2CC3CC(C2C1)CN4C3CCCC4.OS(=O)(=O)O
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. 7,14-methano-2h,6h-dipyrido(1,2-a:1',2'-e)(1,5)diazocine, Dodecahydro-, (7s-(7alpha,7aalpha,14alpha,14abeta))-

    2. Alpha Isosparteine

    3. Alpha-isosparteine

    4. Anhydrous, Sparteine Sulfate

    5. Beta Isosparteine

    6. Beta-isosparteine

    7. D-sparteine

    8. Depasan Retard

    9. Genisteine Alkaloid

    10. L-sparteine

    11. Lupinidin

    12. Lupinidine

    13. Pachycarpine

    14. Pachycarpine Sulfate (1:1), Pentahydrate, (7s-(7alpha,7aalpha,14alpha,14abeta))-isomer

    15. Sparteine

    16. Sparteine Hydrochloride, (7r-(7alpha,7aalpha,14alpha,14abeta))-isomer

    17. Sparteine Hydrochloride, (7s-(7alpha,7aalpha,14alpha,14abeta))-isomer

    18. Sparteine Hydroiodide, (7r-(7alpha,7aalpha,14alpha,14abeta))-isomer

    19. Sparteine Monohydrochloride, (7r-(7alpha,7aalpha,14alpha,14abeta))-isomer

    20. Sparteine Monohydroiodide, (7r-(7alpha,7aalpha,14alpha,14abeta))-isomer

    21. Sparteine Sulfate

    22. Sparteine Sulfate (1:1), (7s-(7alpha,7aalpha,14alpha,14aalpha))-isomer

    23. Sparteine Sulfate (1:1), (7s-(7alpha,7aalpha,14alpha,14abeta))-isomer

    24. Sparteine Sulfate Anhydrous

    25. Sparteine, (+)-isomer

    26. Sparteine, (-)-isomer

    27. Sparteine, (7r-(7alpha,7aalpha,14alpha,14abeta))-isomer

    28. Sparteine, (7r-(7alpha,7abeta,14alpha,14abeta))-isomer

    29. Sparteine, (7s-(7alpha,7aalpha,14alpha,14aalpha))-isomer

    30. Sparteine, (7s-(7alpha,7aalpha,14alpha,14abeta))-isomer

    31. Sparteine, (7s-(7alpha,7abeta,14alpha,14abeta))-isomer

    32. Sulfate Anhydrous, Sparteine

    2.2.2 Depositor-Supplied Synonyms

    1. Sparteine Sulfate

    2. 299-39-8

    3. Tocosimplex

    4. (-)-sparteine (sulfate)

    5. Actospar

    6. Depasan

    7. Sparteal

    8. Spartepur

    9. Spartin

    10. Spartocin

    11. Spatym

    12. Sparm

    13. Spal

    14. Tocosamine Sulfate

    15. Nsc26253

    16. Sparteine, (d)

    17. 7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecane;sulfuric Acid

    18. Wln: T C66 K66 A Hn Pntj &wsqq

    19. Sparteine, Sulfate (1:1)

    20. (-)-sparteine Sulfate

    21. 7,6h-dipyrido[1,2-a:1',2'-e][1,2]diazocine, Dodecahydro-, Sulfate

    22. Nsc-143087

    23. 7,6h-dipyrido[1,2-a:1',2'-e][1,5]diazocine, Dodecahydro-, [7s-(7.alpha.,7a.alpha.,14.alpha.,14a.beta.)]-, Sulfate (1:1)

    24. Nsc376144

    25. Schembl636202

    26. Sulfato--sparteinato (1/1)

    27. Chembl1968726

    28. Dtxsid50952348

    29. (-)-sparteine-sulfate-pentahydrate

    30. Nsc-26253

    31. Nsc143087

    32. Nsc402663

    33. Akos003368041

    34. Am84911

    35. Nsc-376144

    36. Nsc-402663

    37. Ft-0674636

    38. A876348

    2.3 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 332.5 g/mol
    Molecular Formula C15H28N2O4S
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count0
    Exact Mass332.17697855 g/mol
    Monoisotopic Mass332.17697855 g/mol
    Topological Polar Surface Area89.5 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity344
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count4
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Oxytocics

    Drugs that stimulate contraction of the myometrium. They are used to induce LABOR, OBSTETRIC at term, to prevent or control postpartum or postabortion hemorrhage, and to assess fetal status in high risk pregnancies. They may also be used alone or with other drugs to induce abortions (ABORTIFACIENTS). Oxytocics used clinically include the neurohypophyseal hormone OXYTOCIN and certain prostaglandins and ergot alkaloids. (From AMA Drug Evaluations, 1994, p1157) (See all compounds classified as Oxytocics.)

    Anti-Arrhythmia Agents

    Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade. (See all compounds classified as Anti-Arrhythmia Agents.)