712264

Cytisin

≥99.0% (HPLC), ≥99%

• Synonym(e): (−)-Cytisin, (1R,5S)-1,2,3,4,5,6-Hexahydro-1,5-methano-8H-pyrido[1,2a][1,5]diazocin-8-on, (1S,9S)-3,11-Diazatricyclo[7.3.1.0^3,8]trideca-5,7-dien-4-on, Baptitoxin, Laburnin, Sophorin, Ulexin
• Empirische Formel (Hill-System): C₁₁H₁₄N₂O
• CAS-Nummer: 485-35-8
• Molekulargewicht: 190.24
• EG-Nummer: 207-616-0
• MDL-Nummer: MFCD00136048
• UNSPSC-Code: 12352200
• PubChem Substanz-ID: 329763123
• NACRES: NA.22

Eigenschaften

• Qualitätsniveau: 100
• Assay: ≥99%; ≥99.0% (HPLC)
• Form: powder
• Optische Aktivität: [α]/D -108±3°, c = 1% in ethanol
• bp: 218 °C/2 mmHg (lit.)
• mp (Schmelzpunkt): 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
• InChIKey: ANJTVLIZGCUXLD-DTWKUNHWSA-N

Beschreibung

Allgemeine Beschreibung

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.

Anwendung

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.

Biochem./physiol. Wirkung

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

Verpackung

Bottomless glass bottle. Contents are inside inserted fused cone.

Sicherheitshinweise

• Piktogramme: GHS06
• Signalwort: Danger
• H-Sätze: H301 + H311 + H331
• P-Sätze: P261 - P264 - P280 - P301 + P310 - P302 + P352 + P312 - P304 + P340 + P311
• Gefahreneinstufungen: Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral
• Lagerklassenschlüssel: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges