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
CAS Number: 485-35-8
Empirical Formula (Hill Notation): C11H14N2O
Molecular Weight: 190.24
EC Number: 207-616-0
MDL Number: MFCD00136048
Linear Formula: C11H14N2O
Product Type: Chemical
| assay |
≥99% |
| |
≥99.0% (HPLC) |
| bp |
218 °C/2 mmHg (lit.) |
| form |
powder |
| 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 |
| mp |
154-156 °C (lit.) |
| optical activity |
[α]/D -108±3°, c = 1% in ethanol |
| SMILES string |
O=C1C=CC=C2C3CNCC(C3)CN12 |
| Application: |
Cystine may be used as nicotine substitute in nicotine addiction therapy. |
| Application: |
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. |
| Biochem/physiol Actions: |
Potent agonist at α3β4 and α7 nicotinic acetylcholine receptors and partial agonist at α4β2 nicotinic acetylcholine receptors. |
| 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. |
| General description: |
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. |
| Packaging: |
100, 500 mg in glass bottle |
| Packaging: |
Bottomless glass bottle. Contents are inside inserted fused cone. |
| Purity |
≥99%; ≥99.0% (HPLC) |
| bp |
218 °C/2 mmHg (lit.) |
| mp |
154-156 °C (lit.) |
| UNSPSC |
12352200 |
GHS06