Description Biological Functions References
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CYTISINE

Description Biological Functions References
CYTISINE Structure
CYTISINE
  • CAS No.485-35-8
  • Chemical Name:CYTISINE
  • CBNumber:CB1136805
  • Molecular Formula:C11H14N2O
  • Formula Weight:190.24
  • MOL File:485-35-8.mol
CYTISINE Property
  • Melting point: :154-156 °C(lit.)
  • alpha  :D17 -120°
  • Boiling point: :218 °C2 mm Hg(lit.)
  • Density  :1.0815 (rough estimate)
  • refractive index  :1.5700 (estimate)
  • storage temp.  :Store at RT
  • solubility  :439g/l
  • pka :6.11, 13.08(at 25℃)
  • form  :powder
  • color  :light yellow
  • optical activity :[α]/D -108±3°, c = 1% in ethanol
  • Water Solubility  :439g/L(16 ºC)
  • Merck  :14,2789
  • InChIKey :ANJTVLIZGCUXLD-DTWKUNHWSA-N
  • CAS DataBase Reference :485-35-8
  • EWG's Food Scores :1
  • NIST Chemistry Reference :Cytisine(485-35-8)
  • EPA Substance Registry System :Cytisine (485-35-8)
Safety
  • Hazard Codes  :T
  • Risk Statements  :25-36/37/38
  • Safety Statements  :26-28-36/37-45
  • RIDADR  :UN 2811 6.1/PG 3
  • WGK Germany  :3
  • RTECS  :HA4025000
  • HazardClass  :6.1(b)
  • PackingGroup  :III
  • HS Code  :29399990
  • Hazardous Substances Data :485-35-8(Hazardous Substances Data)
  • Toxicity :LD50 in mice (mg/kg): 1.73 i.v.; 9.4 i.p.; 101 orally (Barlow, McLeod)
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordDanger
  • Hazard statements H301-H315-H319-H301+H311+H331
  • Precautionary statements P264-P270-P301+P310+P330-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P405-P501-P261-P280-P302+P352+P312-P304+P340+P312-P403+P233
CYTISINE Price More Price(9)
  • Brand: Sigma-Aldrich
  • Product number: 712264
  • Product name : Cytisine
  • Purity: ≥99.0% (HPLC), ≥99%
  • Packaging: 100mg
  • Price: $163
  • Updated: 2019/12/02
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: 712264
  • Product name : Cytisine
  • Purity: ≥99.0% (HPLC), ≥99%
  • Packaging: 500mg
  • Price: $585
  • Updated: 2019/12/02
  • Buy: Buy
  • Brand: TCI Chemical
  • Product number: C2609
  • Product name : (-)-Cytisine
  • Purity: >98.0%(GC)(T)
  • Packaging: 1g
  • Price: $581
  • Updated: 2019/12/02
  • Buy: Buy
  • Brand: TCI Chemical
  • Product number: C2609
  • Product name : (-)-Cytisine
  • Purity: >98.0%(GC)(T)
  • Packaging: 100mg
  • Price: $115
  • Updated: 2019/12/02
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: C2899
  • Product name : Cytisine
  • Purity: ≥99%, powder
  • Packaging: 250mg
  • Price: $1250
  • Updated: 2019/12/02
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CYTISINE Chemical Properties,Usage,Production

  • Description Cytisine (also known as baptitoxine and sophorine) is a kind of naturally occurring alkaloid that can be found in several plant genera including Laburnum and Cytisus in the family Fabaceae. It has been shown that it is effective in the smoking cessation treatment. It is a low efficacy partial agonist of alpha4-beta2 nicotinic acetylcholine receptors, which is the central target of the nicotine that facilitates addiction. Cytisine is capable of reducing the effect of nicotine on dopamine release on the mesolimbic system as well as attenuating the nicotine withdrawal symptoms. Cytisine is also a useful reagent for organic chemistry such as being used for the manufacture of sparteine surrogate.
  • Biological Functions Cytisine has a physiological action similar to that of nicotine. Poisoning in Europe is generally from laburnum trees (Laburnum anagyroides, Leguminosae), while, in the tropics and America, Sophora species (Leguminosae) are often the cause. The alkaloid occurs in all parts of laburnum, but is most concentrated in the seeds, which can be mistaken for peas by children. Cytisine does not always affect cattle, but this compound can be excreted in milk and so poison children.
  • References https://en.wikipedia.org/wiki/Cytisine
    https://www.drugbank.ca/drugs/DB09028
  • Chemical Properties Off-White to Tan Crystalline Solid
  • Uses antiinflammatory, respiratory stimulant
  • Uses Toxic priniciple in seed of Laburnum anagyroides and other Leguminosae. A neuronal nicotinic acetylcholine agonist
  • Uses Cytisine occurs in the seeds of Cytisus labur num L. and other Leguminosae.
  • Definition ChEBI: An organic heterotricyclic compound that is the toxic principle in Laburnum seeds and is found in many members of the Fabaceae (legume, pea or bean) family. An acetylcholine agonist, it is widely used throughout Eastern Europe as n aid to giving up smoking.
  • Health Hazard Cytisine is highly toxic to humans and ani mals. Ingestions may cause nausea, vomiting,and convulsions. Death may occur from respiratory failure
    LD50 value, oral (rats): 101 mg/kg.
  • Biological Activity A potent, selective agonist at neuronal nicotinic receptors. Acts as a partial agonist at β 2-containing nicotinic receptors.
  • Purification Methods Crystallise cytisine from acetone and sublime it in a vacuum. Its solubilities are: 77% (H2O), 7.7% (Me2CO), 28.6% (EtOH), 3.3% (*C6H6), 50% (CHCl3) but it is insoluble in pet ether. The tartrate has m 206-207o [] D +45.9o, the N-tosylate has m 206-207o, and the N-acetate has m 208o. [Bohlmann et al. Angew Chem 67 708 1955, van Tamelen & Baran J Am Chem Soc 77 4944 1955, Isolation: Ing J Chem Soc 2200 1931, Govindachari et al. J Chem Soc 3839 1957, Abs config: Okuda et al. Chem Ind (London) 1751 1961, Beilstein 24 H 134, 24 I 244, 24 II 70, 24 III/IV 321.] TOXIC.
CYTISINE Preparation Products And Raw materials
Raw materials
Preparation Products
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485-35-8, CYTISINERelated Search:
  • SOPHORINE
  • Cytisinicline
  • LABURNIN
  • LABURNINE
  • (1R-5S)-1,2,3,4,5,6-HEXAHYDRO-1,5-METHANO-8H-PYRIDO[1,2-A][1,5]DIAZOCIN-8-ONE
  • 7,11-DIAZATRICYCLO[7.3.1.0(2,7)]TRIDECA-2,4-DIEN-6-ONE
  • 1,5-Methano-8H-pyrido1,2-a1,5diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R,5S)-
  • Baptitixine
  • (-)-Cytisine, (1S,9S)-3,11-Diazatricyclo[7.3.1.03,8]trideca-5,7-dien-4-one, (1R,5S)-1,2,3,4,5,6-Hexahydro-1,5-methano-8H-pyrido[1,2a][1,5]diazocin-8-one
  • (-)-Cytisine 19000
  • (1R,5S)-1,2,3,4,5,6-Hexahydro-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one
  • CYTISINE(LABURNIN)(P)
  • Cytisine,()-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
  • Cytisine(SALTDATA: FREE)
  • (-)-cytistine
  • (1S,9S)-3,11-Diazatricyclo[7.3.1.0]trideca-5,7-dien-4-one
  • (1R,5S)-
  • (1R,5S)-3,4,5,6-Tetrahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-8(2H)-one
  • Cytisine (Baphitoxine, Sophorine)
  • Tsitafat
  • Baphitoxine, Sophorine
  • Cytisine >=99.0% (HPLC), >=99%
  • (-)-Cytisine for synthesis
  • (-)-Cytisine - CAS 485-35-8 - Calbiochem
  • Cytisine 485-35-8
  • 1,2,3,4,5,6-Hexahydro-1,5-methano-8H-pyrido[1,2-a][1,5]diazocin-8-one
  • 1,2,3,4,5,6-Hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin
  • 1,5-Methano-8H-pyrido(1,2-a)(1,5)diazocin-8-one, 1,2,3,4,5,6-hexahydro-
  • 1,5-Methano-8H-pyrido[1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R)-
  • 1,5-Methano-8H-pyrido[1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R-cis)-
  • 2-a)(1,5)diazocin-8-one,1,2,3,4,5,6-hexahydro-5-methano-8h-pyrido(1
  • 5)diazocin-8-one,1,2,3,4,5,6-hexahydro-5-methano-8h-pyrido((1r)-2-a)(1
  • 5-methano-8h-pyrido[1,2-a][1,5]diazocin-8-one,1,2,3,4,5,6-hexahydro-(1the
  • Baptitoxin
  • Baptitoxine
  • Citizin
  • Cystisine
  • Cytisin
  • Cytiton
  • Cytitone
  • Cytizin
  • Pyrido[1, 2-a]-1, 5-perhydrodiazocin-1(11)-one, 5, 9-methano-
  • Tabax
  • Tabex
  • Tsitizin
  • Ulexin
  • ULEXINE
  • BABTITOSINE
  • (-)-CYTISINE
  • CYTISINE
  • (-)-CYTISINE(1R,5S)-1,2,3,4,5,6-HEXAHYDRO-1,5-METHANO-8H-PYRIDO[1,2-A][1,5]DIAZOCIN-8-ONE
  • 485-35-8
  • 458-35-8
  • 98485-35-8
  • 485-38-8
  • Cell Biology
  • Cell Signaling and Neuroscience
  • BioChemical