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
Show more names
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
- Formal charge
- 0
- Complexity
- 332
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
- solubility
- 439 g/l · 439g/l
- pka
- 6.11 · 6.11, 13.08(at 25℃)
- form
- powder
- color
- light yellow
- optical activity
- -108 · [α]/D -108±3°, c = 1% in ethanol
- Water Solubility
- 439 g/L · 439g/L(16 ºC)
- Merck
- 14 · 14,2789
- 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
- SMILES
- O=C1C=CC=C2C3CNCC(C3)CN12
- LogP
- 0.172 · 0.172 (est)
- CAS DataBase Reference
- 485 · 485-35-8
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 53 S5U404NU · 53S5U404NU
- ATC code
- 7 BA04 · N07BA04
- NIST Chemistry Reference
- Cytisine(485-35-8)
- EPA Substance Registry System
- Cytisine (485-35-8)
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301+H311+H331
- Precautionary statements
- 261 · P261-P264-P280-P301+P310-P302+P352+P312-P304+P340+P311
- PPE
- 2 · Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
- Hazard Codes
- T
- Risk Statements
- 25 · 25-36/37/38
- Safety Statements
- 26 · 26-28-36/37-45
- RIDADR
- 2811 · UN 2811 6.1/PG 3
- WGK Germany
- 3 · 3
- RTECS
- 4025000 · HA4025000
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1(b)
- PackingGroup
- III
- HS Code
- 29399990 · 29399990
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 3 DermalAcute · Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 Oral
- Hazardous Substances Data
- 485 · 485-35-8(Hazardous Substances Data)
- Toxicity
- 50 in · LD50 in mice (mg/kg): 1.73 i.v.; 9.4 i.p.; 101 orally (Barlow, McLeod)
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
- Toxicity
- LD50 in mice (mg/kg): 1.73 i.v.; 9.4 i.p.; 101 orally (Barlow, McLeod)
- risk_code
- 25-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T
- safety_code
- 26-28-36/37-45
- hazard_class
- 6.1(b)
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- III
- Hazard statements
- H301+H311+H331
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 Oral
- Precautionary statements
- P261-P264-P280-P301+P310-P302+P352+P312-P304+P340+P311
- Hazardous Substances Data
- 485-35-8(Hazardous Substances Data)
Chemistry & industry
Applications
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.
Upstream & downstream products
Downstream products
Suppliers100 total
Additional notes
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
Compound notes
Loading…