712264

Cytisine

≥99.0% (HPLC), ≥99%

• Synonym(s): (−)-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[7.3.1.0^3,8]trideca-5,7-dien-4-one, Baptitoxin, Laburnin, Sophorine, Ulexine
• Empirical Formula (Hill Notation): C₁₁H₁₄N₂O
• CAS Number: 485-35-8
• Molecular Weight: 190.24
• EC Number: 207-616-0
• MDL number: MFCD00136048
• UNSPSC Code: 12352200
• PubChem Substance ID: 329763123
• NACRES: NA.22

Properties

• Quality Level: 100
• Assay: ≥99%; ≥99.0% (HPLC)
• form: powder
• 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.

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 Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H301 + H311 + H331
• Precautionary Statements: P261 - P264 - P280 - P301 + P310 - P302 + P352 + P312 - P304 + P340 + P311
• Hazard Classifications: Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral
• Storage Class Code: 6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves