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Sparteine Sulfate

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Synopsis

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Chemistry

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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

Sparteine Sulfate

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 Formula	C₁₅H₂₈N₂O₄S
Molecular Weight	332.5 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	0
Exact Mass	332.17697855 g/mol
Monoisotopic Mass	332.17697855 g/mol
Topological Polar Surface Area	89.5 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	344
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	4
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

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.)

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