Structure via PubChem · Public domain (PubChem)
(−)-sparteine
Sign in to saveSparteine 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.
In the Vinony graph
Vinony's link graph records 375 inbound references to (−)-sparteine, and connects out to calcium, magnesium and International Standard Book Number.
It is catalogued under topics including Antiarrhythmic agents, Drugboxes which contain changes to verified fields and Drugboxes which contain changes to watched fields.
Vinony links it to 17 Wikipedia language editions.
Chemical data
- Formula
- C15H26N2
- Molecular weight
- 234.38 g/mol
- IUPAC name
- (1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecane
- SMILES
- C1CCN2C[C@@H]3C[C@H]([C@H]2C1)CN4[C@H]3CCCC4
- InChIKey
- SLRCCWJSBJZJBV-ZQDZILKHSA-N
- XLogP
- 2.5
- Polar surface area
- 6.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
1,343 papers- Sparteine.Archives internationales de pharmacodynamie et de therapie · 1948
- Sparteine as an anticonvulsant drug: Evidence and possible mechanism of action.Seizure · 2016
- The genetic polymorphism of debrisoquine/sparteine metabolism-molecular mechanisms.Pharmacology & therapeutics · 1990
- [Pachycarpine].Fel'dsher i akusherka · 1954
- [CORDISANOL].Medizinische Klinik · 1953
via PubMed
Wikidata facts
- Has part
- carbon
- Mass
- 234.209599
Show 8 more facts
- isomeric SMILES
- C1CCN2C[C@@H]3C[C@H]([C@H]2C1)CN4[C@H]3CCCC4
- chemical formula
- C₁₅H₂₆N₂
- found in taxon
- Wiborgia sericea
- Commons category
- Sparteine
- defined daily dose
- 0.2
- canonical SMILES
- N12CCCCC1C3CN4CCCCC4C(C2)C3
- has characteristic
- bitterness
- described by source
- New International Encyclopedia
via Wikidata · CC0
~3 min read
Encyclopedic overview
5 sectionsContents
- Biosynthesis
- Via 17-oxosparteine synthase
- See also
- References
- External links
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.
Excerpted from Wikipedia’s “(−)-sparteine” article, available under the CC BY-SA 4.0 licence.