Cytisine

HCID 10235

Basic information

CAS
485-35-8
Standard SMILES
O=c1cccc2n1C[C@@H]1CNC[C@H]2C1
InChIKey
ANJTVLIZGCUXLD-DTWKUNHWSA-N
Molecular formula
C11H14N2O
Average molar mass
190.24 g/mol
Monoisotopic mass
190.11061307

Names & identifiers

Preferred name
Cytisine
IUPAC
(1R,9S)-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one
English name
CYTISINE
Molecular formula
C11H14N2O
Molecular weight
190.24

Names & synonyms

CYTISINE485-35-8BaptitoxineSophorineCytisiniclineBaptitoxinCytitonLaburninUlexineUlexinCytitoneCitizin
Show more names
CytisinTabax(-)-CytisineCytisinicline/Cytisin (6039-Sopharma)
CystisineCytizin(1r,5s)-1,2,3,4,5,6-Hexahydro-8h-1,5-Methanopyrido[1,2-A][1,5]diazocin-8-One6039 SopharmacitisiniclinaNSC-40728253S5U404NU(1R,9S)-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one

Database identifiers

CAS
485-35-8
PubChem CID
10235
DTXSID
DTXSID00883395
ChEMBL
CHEMBL497939
ChEBI
CHEBI:4055
UNII
53S5U404NU
EC Number
207-616-0
Nikkaji
J9.571K

Properties

Computed structural properties

XLogP
0.2
Topological polar surface area
32.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
14

Physicochemical properties

Melting point
154 · 154-156 °C (lit.)
Boiling point
218 °C/2 · 218 °C/2 mmHg (lit.)
alpha
17 · D17 -120°
Density
1.0815 · 1.0815 (rough estimate)
refractive index
1.57 · 1.5700 (estimate)
storage temp.
2 · Keep in dark place,Sealed in dry,2-8°C

Safety & regulation

Safety data

PPE
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
wgk
3
tsca
TSCA listed
rtecs
HA4025000
ridadr
UN 2811 6.1/PG 3
hs_code
29399990

Chemistry & industry

Applications · 7 items

DescriptionCytisine (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.

DescriptionIt is an alkaloid that occurs naturally in several plant genera, such as Laburnum and Cytisus of the family Fabaceae. Pi-Zhen-Ye-Huang-Hua (Thermopsis lanceolata R.Br) contains large amount of cytisine, and it is distributed in the northeast, north, and northwest of China. This herb has been traditionally used for treating cough in China and was recorded in “Yue-Wang-Yao-Zhen,”“Jing-ZhuBen-Cao,”“Zhong-Hua-Ben-Cao,” and “Ning-Xia-Zhong-Cao-Yao-Shou-Ce.”

HistoryThe largest amount of cytisine (about 1–5%) is also found in the seeds of common garden decorative plant Du-Dou (Laburnum anagyroides). In the early twentieth century, cytisine was identified as the toxic component of this plant. The extracts of Laburnum seeds or flowers have been used in traditional medicine for hundreds of years. In the Second World War, the leaves of Laburnum anagyroides were used as a tobacco substitute by soldiers. In 1960s, cytisine was firstly used as a smoking cessation aid in Bulgaria. The pharmacological and clinical studies of cytisine were also conducted in other Eastern European countries such as Poland and Russia. These results were promising. Stoyanov S. and Yanachkova M. studied 70 volunteers with a long experience in smoking. They found that 57% volunteers stopped smoking and 31.4% volunteers decreased cigarettes: reduction of the cigarettes smoked from 20–30 to 3–4 a day. Cytisine was developed and marked as Tabex (Sopharma, Bulgaria), which has been widely distributed in the Eastern Europe .

Usesantiinflammatory, respiratory stimulant

UsesToxic 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.

UsesCytisine occurs in the seeds of Cytisus labur num L. and other Leguminosae.

General DescriptionCystine ((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.

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
山西玉宁生物科技有限公司13623677056
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
Additional notes · 1 item

DefinitionChEBI: 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.

Related reactions

3 records

Compound notes

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