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712264 Sigma-Aldrich

Cytisine

≥99.0% (HPLC), ≥99%

Synonym: (−)-Cytisine, (1R,5S)-1,2,3,4,5,6-Hexahydro-1,5-methano-8H-pyrido[1,2a][1,5]diazocin-8-one, (1S,9S)-3,11-Diazatricyclo[7.3.1.03,8]trideca-5,7-dien-4-one, Baptitoxin, Laburnin, Sophorine, Ulexine

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Building Blocks, Complex Molecules
Quality Level   100
assay   ≥99%
  ≥99.0% (HPLC)
optical activity   [α]/D -108±3°, c = 1% in ethanol
bp   218 °C/2 mmHg (lit.)
mp   154-156 °C (lit.)
SMILES string   O=C1C=CC=C2C3CNCC(C3)CN12
InChI   1S/C11H14N2O/c14-11-3-1-2-10-9-4-8(5-12-6-9)7-13(10)11/h1-3,8-9,12H,4-7H2/t8-,9+/m0/s1
InChI key   ANJTVLIZGCUXLD-DTWKUNHWSA-N

Description

General description

Cystine ((1R,5S)-1,2,3,4,5,6-hexahydro-1,5-methano-8H-pyrido[1,2a][1,5]diazocin-8-one) displays classical antidepressant action in various animal models of antidepressant efficacy. Infrared and Raman spectral studies suggest that it has two stable conformers.

Cytisine was found to be more effective than nicotine-replacement therapy in helping smokers to quit smoking. It is an α4 β2 nicotinic receptor partial agonist. It is a plant alkaloid which is commercially extracted for use as a smoking cessation medication. Preparation of nicotine partial agonist cytisine via “in situ” Stille or Suzuki biaryl pyridine coupling has been reported. Cytisine is a competitive partial agonist at α4 subunit-containing nicotinic acetylcholine (nACh) receptors while at homomeric α7-nACh receptors it behaves as a full agonist with a relatively lower potency.

Application

Cystine may be used as nicotine substitute in nicotine addiction therapy.

Cytisine is suitable for use in a study to compare the effects of varenicline and cytisine on ethanol consumption by rats bred for many generations as high ethanol drinkers.

Packaging

100, 500 mg in glass bottle

Biochem/physiol Actions

Potent agonist at α3β4 and α7 nicotinic acetylcholine receptors and partial agonist at α4β2 nicotinic acetylcholine receptors.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
RIDADR 
UN 1544PSN1 6.1 / PGIII
WGK Germany 
WGK 3
RTECS 
HA4025000
Protocols & Articles

Articles

(+)-Sparteine Surrogate

Until recently, sparteine, a widely used ligand in asymmetric synthesis1 was only commercially available in one enantiomeric form. O'Brien and his coworkers have designed several (+)-sparteine surrog...
Keywords: Asymmetric synthesis, Desymmetrizations, Grignard Reaction, Hydrogenations, Ligands, Lithiations, Rearrangements, Reductions

Peer-Reviewed Papers
15

References

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