Sparteine

Sparteine

Clinical data
Other names	(6R,8S,10R,12S)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecane
AHFS/Drugs.com	International Drug Names
ATC code	C01BA04 (WHO)
Identifiers
IUPAC name (7α,9α)-sparteine
CAS Number	90-39-1 Y
PubChem CID	644020
DrugBank	DB06727 Y
ChemSpider	559096 Y
UNII	298897D62S
KEGG	D01041 Y
ChEBI	CHEBI:28827 Y
ChEMBL	ChEMBL44625 N
CompTox Dashboard (EPA)	DTXSID4023591
ECHA InfoCard	100.001.808
Chemical and physical data
Formula	C15H26N2
Molar mass	234.387 g·mol−1
3D model (JSmol)	Interactive image
Density	1.02 g/cm3
Melting point	30 °C (86 °F)
Boiling point	325 °C (617 °F)
Solubility in water	3.04 mg/mL (20 °C)
SMILES C1CCN2C[C@@H]3C[C@H]([C@H]2C1)CN4[C@H]3CCCC4
InChI InChI=1S/C15H26N2/c1-3-7-16-11-13-9-12(14(16)5-1)10-17-8-4-2-6-15(13)17/h12-15H,1-11H2/t12-,13-,14-,15+/m0/s1 Y Key:SLRCCWJSBJZJBV-ZQDZILKHSA-N Y
NY (what is this?)  (verify)

Sparteine is a class 1a antiarrhythmic agent and sodium channel blocker. It is an alkaloid and can be extracted from scotch broom. It is the predominant alkaloid in Lupinus mutabilis, and is thought to chelate the bivalent metals calcium and magnesium. It is not FDA approved for human use as an antiarrhythmic agent, and it is not included in the Vaughan Williams classification of antiarrhythmic drugs.

It is also used as a chiral ligand in organic chemistry, especially in syntheses involving organolithium reagents.