Basic information Description Biological Functions References Safety Supplier Related
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CYTISINE

Basic information Description Biological Functions References Safety Supplier Related

CYTISINE Basic information

Product Name:
CYTISINE
Synonyms:
  • SOPHORINE
  • 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
  • (-)-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
CAS:
485-35-8
MF:
C11H14N2O
MW:
190.24
EINECS:
207-616-0
Product Categories:
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Heterocyclic Compounds
  • Neurochemicals
  • Nicotine Derivatives
  • Pharmaceuticals
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
  • CYTITON
  • natural product
  • Inhibitors
Mol File:
485-35-8.mol
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CYTISINE Chemical Properties

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
NIST Chemistry Reference
Cytisine(485-35-8)
EPA Substance Registry System
Cytisine (485-35-8)
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Safety Information

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)

MSDS

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CYTISINE Usage And Synthesis

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. 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.

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