(1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecane; sulfuric acid

• ChemBase ID: 177711
• Molecular Formular: C15H28N2O4S
• Molecular Mass: 332.45882
• Monoisotopic Mass: 332.17697839
• SMILES: C1[C@H]2[C@H]3CCCCN3C[C@@H]([C@@H]3CCCCN13)C2.S(=O)(=O)(O)O
• Canonical SMILES: C1CC[C@@H]2N(C1)C[C@@H]1C[C@H]2CN2[C@@H]1CCCC2.OS(=O)(=O)O
• 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)/t12?,13?,14-,15+
• InChIKey: FCEHFCFHANDXMB-VZDLBMALSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.0^2,^7.0^1^0,^1^5]heptadecane; sulfuric acid
• IUPAC Traditional name: sparteine; sulfuric acid
• Synonyms: (7S,7aR,14S,14aS)-Dodecahydro-7,14-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine Sulfate; Sparteine Sulfate; NSC 143087; NSC 26253; NSC 402663; Spartepur; Spal; Spareng; Sparm; Sparteal; Spartocin; Spartin; Spatym; Tocosimplex; [7S-(7α,7aα,14α,14aβ)]-Dodecahydro-7,14-methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocine Sulfate; Sparteine Sulfate

Database IDs

• CAS Number: 299-39-8
• PubChem SID: 164233621
• PubChem CID: 23616742

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -3.3671618
• LogD (pH = 7.4): -0.38936847
• Log P: 2.0278275
• Molar Refractivity: 71.823 cm^3
• Polarizability: 28.518066 Å^3
• Polar Surface Area: 6.48 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 129-131°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - S679500

A class 1a antiarrhythmic agent; a sodium channel blocker.

REFERENCES

• Spasov, V. et al.: Farmatsiya, 28, 34 (1978)
• Zetler, G. et al.: Arzneim.-Forsch., 30, 1497 (1978)
• Dengler, H.J. et al.: Pharmacol Clin., 2, 189 (1978)