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Sparteine information


Sparteine
Clinical data
Other names(6R,8S,10R,12S)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecane
AHFS/Drugs.comInternational Drug Names
ATC code
  • C01BA04 (WHO)
Identifiers
IUPAC name
  • (7α,9α)-sparteine
CAS Number
  • 90-39-1 checkY
PubChem CID
  • 644020
DrugBank
  • DB06727 checkY
ChemSpider
  • 559096 checkY
UNII
  • 298897D62S
KEGG
  • D01041 checkY
ChEBI
  • CHEBI:28827 checkY
ChEMBL
  • ChEMBL44625 ☒N
CompTox Dashboard (EPA)
  • DTXSID4023591 Edit this at Wikidata
ECHA InfoCard100.001.808 Edit this at Wikidata
Chemical and physical data
FormulaC15H26N2
Molar mass234.387 g·mol−1
3D model (JSmol)
  • Interactive image
Density1.02 g/cm3
Melting point30 °C (86 °F)
Boiling point325 °C (617 °F)
Solubility in water3.04 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 checkY
  • Key:SLRCCWJSBJZJBV-ZQDZILKHSA-N checkY
 ☒NcheckY (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.

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Sparteine

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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...

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Cytisus scoparius

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glycosides (genistin), as well as allelopathic quinolizidine alkaloids (mostly sparteine, lupanine, scoparin and hydroxy-derivatives), which defend the plant against...

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Cytisine

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anagyroides seeds was used as a starting material for the preparation of "(+)-sparteine surrogate," for the preparation of enantiomerically enriched lithium anions...

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Lupinus arcticus

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contains a neurotoxin called sparteine, possibly as a deterrent to herbivores such as the snowshoe hare. The levels of sparteine in the leaves cycle, becoming...

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Organolithium reagent

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bonds. The addition of strongly donating ligands, such as TMEDA and (-)-sparteine, can displace coordinating solvent molecules in silyllithiums. It is possible...

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Cocaine

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Quinolizidine alkaloids

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including camoensin the spartein type with 66 structures, including sparteine, lupanine, angustifoline the α-pyridone type with 25 structures, including...

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Ketamine

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Quinolizidine

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nitrogen-containing heterocyclic compound. Some alkaloids (e.g. cytisine and sparteine) are derivatives of quinolizidine. Quinolizidine alkaloids, such as nupharine...

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Alkaloid

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caffeine (1820), coniine (1827), nicotine (1828), colchicine (1833), sparteine (1851), and cocaine (1860). The development of the chemistry of alkaloids...

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Promethazine

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Chlorphenamine

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Gabapentin

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Calcium channel blocker

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Bispidine

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diamine. Although synthetic, it is related structurally to natural alkaloid sparteine. It is a white crystalline solid. It has been widely investigated as a...

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Carbamazepine

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Aldol reaction

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"Evans syn" or "non-Evans syn" adducts by simply varying the amount of (−)-sparteine. The reaction is believed to proceed via six-membered, titanium-bound...

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Wacker process

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ligands can be used to enforce the Markovnikov regioselectivity. The use of sparteine as a ligand (Figure 2, A) favors nucleopalladation at the terminal carbon...

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Lamotrigine

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Amlodipine

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Spartium

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receptors followed by a persistent inhibition caused by desensitization. The sparteine has an effect of the heart, reducing its sensitivity and conductivity...

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Retama monosperma

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from different parts of the plant. In particular, the presence of (+)-sparteine, α- and β-isosparteine, (+)-17-oxosparteine, (-)-lupanine, 5,6-dehydrolupanine...

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Phenibut

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Benzonatate

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Cholesterol

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Kava

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Pregabalin

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Propranolol

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Lidocaine

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