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Cas Database |
| Name |
Cytisine |
EINECS | 207-616-0 |
| CAS No. | 485-35-8 | Density | 1.24 g/cm3 |
| PSA | 34.03000 | LogP | 0.88380 |
| Solubility | Soluble to 100 mM in Water | Melting Point |
154-156 °C(lit.) |
| Formula | C11H14N2O | Boiling Point | 413 °C at 760 mmHg |
| Molecular Weight | 190.245 | Flash Point | 203.6 °C |
| Transport Information | N/A | Appearance | Off-white to tan crystalline solid |
| Safety | 26-28-36/37-45 | Risk Codes | 25-36/37/38 |
| Molecular Structure |
|
Hazard Symbols |
 T
|
| Synonyms |
1,5-Methano-8H-pyrido[1,2-a][1,5]diazocin-8-one,1,2,3,4,5,6-hexahydro-, (1R)-;Cytisine (6CI,8CI);(-)-Cytisine;Baptitoxin;Baptitoxine;Cytisin;Cytiton;Cytitone;Laburnin;Sophorin;Sophorine;Tabex;Tsitafat;Ulexin;Ulexine;1,5-Methano-8H-pyrido[1,2-a][1,5]diazocin-8-one,1,2,3,4,5,6-hexahydro-, (1R,5S)-; |
Article Data | 9 |
Cytisine Synthetic route
- 667940-15-0
(6R,7R,9R)-(-)-N-benzyloxycarbonyl-cytisine
- 485-35-8
cytisine
| Conditions | Yield |
|---|---|
| With hydrogenchloride In tetrahydrofuran for 3h; Heating; | 78% |
- 485-35-8
cytisine
| Conditions | Yield |
|---|---|
| With potassium carbonate; thiophenol In N,N-dimethyl-formamide; acetonitrile at 45℃; for 0.5h; | 96% |
- 485-35-8
cytisine
| Conditions | Yield |
|---|---|
| Stage #1: (1R,9R)-11-tert-butoxycarbonyl-7,11-diazatricyclo[7.3.1.02,7]tridec-2,4-dien-6,10-dione With methanol; sodium tetrahydroborate at 0 - 20℃; for 2h; Stage #2: With triethylsilane; boron trifluoride diethyl etherate In dichloromethane at -78 - 20℃; for 15h; | 79% |
- 206554-22-5
(3S,5R)-(+)-3-acetoxymethyl-5-formyl-1-piperidine-1-carbvoxylic acid benzyl ester
- 485-35-8
cytisine
| Conditions | Yield |
|---|---|
| Multi-step reaction with 11 steps 1.1: (-)-B-methoxydiisopinocampheylborane / diethyl ether / 1.25 h / -78 - 20 °C 1.2: diethyl ether / -78 - 20 °C / Acid hydrolysis 1.3: 76 percent / aq. NaOH; aq. H2O2 / 3 h / Heating 2.1: 99 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C 3.1: 87 percent / NaN3 / dimethylformamide / 2 h / 80 °C 4.1: Ph3P / tetrahydrofuran 4.2: 66 percent / H2O 5.1: 89 percent / Et3N; DMAP / CH2Cl2 / 4.5 h / 0 - 20 °C 6.1: 79 percent / Cl2Ru(CHPh)(PCy3)2 / CH2Cl2 / 12 h / Heating 7.1: 98 percent / NaOH / tetrahydrofuran / 2 h / 20 °C 8.1: 67 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C 9.1: 89 percent / NaH / tetrahydrofuran / 0 - 20 °C 10.1: 50 percent / DDQ / dioxane / 4 h / 110 °C 11.1: 78 percent / HCl / tetrahydrofuran / 3 h / Heating View Scheme |
- 206761-38-8
(3S,5R)-3-acetoxymethyl-5-hydroxymethylpiperidine-1-carboxylic acid benzyl ester
- 485-35-8
cytisine
| Conditions | Yield |
|---|---|
| Multi-step reaction with 12 steps 1.1: (-)-B-methoxydiisopinocampheylborane / diethyl ether / 1.25 h / -78 - 20 °C 1.2: diethyl ether / -78 - 20 °C / Acid hydrolysis 1.3: 76 percent / aq. NaOH; aq. H2O2 / 3 h / Heating 2.1: 99 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C 3.1: 87 percent / NaN3 / dimethylformamide / 2 h / 80 °C 4.1: Ph3P / tetrahydrofuran 4.2: 66 percent / H2O 5.1: 89 percent / Et3N; DMAP / CH2Cl2 / 4.5 h / 0 - 20 °C 6.1: 79 percent / Cl2Ru(CHPh)(PCy3)2 / CH2Cl2 / 12 h / Heating 7.1: 98 percent / NaOH / tetrahydrofuran / 2 h / 20 °C 8.1: 67 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C 9.1: 89 percent / NaH / tetrahydrofuran / 0 - 20 °C 10.1: 50 percent / DDQ / dioxane / 4 h / 110 °C 11.1: 78 percent / HCl / tetrahydrofuran / 3 h / Heating View Scheme |
- 667940-16-1
(3S,5R,1'S)-(-)-3-acetoxymethyl-5-(1'-hydroxybut-3'-enyl)-1-piperidine-1-carboxylic acid benzyl ester
- 485-35-8
cytisine
| Conditions | Yield |
|---|---|
| Multi-step reaction with 10 steps 1.1: 99 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C 2.1: 87 percent / NaN3 / dimethylformamide / 2 h / 80 °C 3.1: Ph3P / tetrahydrofuran 3.2: 66 percent / H2O 4.1: 89 percent / Et3N; DMAP / CH2Cl2 / 4.5 h / 0 - 20 °C 5.1: 79 percent / Cl2Ru(CHPh)(PCy3)2 / CH2Cl2 / 12 h / Heating 6.1: 98 percent / NaOH / tetrahydrofuran / 2 h / 20 °C 7.1: 67 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C 8.1: 89 percent / NaH / tetrahydrofuran / 0 - 20 °C 9.1: 50 percent / DDQ / dioxane / 4 h / 110 °C 10.1: 78 percent / HCl / tetrahydrofuran / 3 h / Heating View Scheme |
- 667940-11-6
(3S,5R,1'R)-(-)-3-acetoxymethyl-5-(1'-azidobut-3'-enyl)-1-piperidine-1-carboxylic acid benzyl ester
- 485-35-8
cytisine
| Conditions | Yield |
|---|---|
| Multi-step reaction with 8 steps 1.1: Ph3P / tetrahydrofuran 1.2: 66 percent / H2O 2.1: 89 percent / Et3N; DMAP / CH2Cl2 / 4.5 h / 0 - 20 °C 3.1: 79 percent / Cl2Ru(CHPh)(PCy3)2 / CH2Cl2 / 12 h / Heating 4.1: 98 percent / NaOH / tetrahydrofuran / 2 h / 20 °C 5.1: 67 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C 6.1: 89 percent / NaH / tetrahydrofuran / 0 - 20 °C 7.1: 50 percent / DDQ / dioxane / 4 h / 110 °C 8.1: 78 percent / HCl / tetrahydrofuran / 3 h / Heating View Scheme |
- 667940-18-3
(3S,5R)-3-Acetoxymethyl-5-((R)-1-amino-but-3-enyl)-piperidine-1-carboxylic acid benzyl ester
- 485-35-8
cytisine
| Conditions | Yield |
|---|---|
| Multi-step reaction with 7 steps 1: 89 percent / Et3N; DMAP / CH2Cl2 / 4.5 h / 0 - 20 °C 2: 79 percent / Cl2Ru(CHPh)(PCy3)2 / CH2Cl2 / 12 h / Heating 3: 98 percent / NaOH / tetrahydrofuran / 2 h / 20 °C 4: 67 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C 5: 89 percent / NaH / tetrahydrofuran / 0 - 20 °C 6: 50 percent / DDQ / dioxane / 4 h / 110 °C 7: 78 percent / HCl / tetrahydrofuran / 3 h / Heating View Scheme |
- 667940-10-5
(3S,5R,1'S)-(+)-3-acetoxymethyl-5-(1'-methanesulfonyloxybut-3'-enyl)-1-piperidine-1-carboxylic acid benzyl ester
- 485-35-8
cytisine
| Conditions | Yield |
|---|---|
| Multi-step reaction with 9 steps 1.1: 87 percent / NaN3 / dimethylformamide / 2 h / 80 °C 2.1: Ph3P / tetrahydrofuran 2.2: 66 percent / H2O 3.1: 89 percent / Et3N; DMAP / CH2Cl2 / 4.5 h / 0 - 20 °C 4.1: 79 percent / Cl2Ru(CHPh)(PCy3)2 / CH2Cl2 / 12 h / Heating 5.1: 98 percent / NaOH / tetrahydrofuran / 2 h / 20 °C 6.1: 67 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C 7.1: 89 percent / NaH / tetrahydrofuran / 0 - 20 °C 8.1: 50 percent / DDQ / dioxane / 4 h / 110 °C 9.1: 78 percent / HCl / tetrahydrofuran / 3 h / Heating View Scheme |
- 667940-08-1
(3S,5R,1'R)-(+)-3-acetoxymethyl-5-(1'-acryloylaminobut-3'-enyl)-1-piperidine-1-carboxylic acid benzyl ester
- 485-35-8
cytisine
| Conditions | Yield |
|---|---|
| Multi-step reaction with 6 steps 1: 79 percent / Cl2Ru(CHPh)(PCy3)2 / CH2Cl2 / 12 h / Heating 2: 98 percent / NaOH / tetrahydrofuran / 2 h / 20 °C 3: 67 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C 4: 89 percent / NaH / tetrahydrofuran / 0 - 20 °C 5: 50 percent / DDQ / dioxane / 4 h / 110 °C 6: 78 percent / HCl / tetrahydrofuran / 3 h / Heating View Scheme |
Cytisine Chemical Properties
Following is the structure of Cytisine (CAS NO.485-35-8):
Molecular Formula: C11H14N2O
Molecular Weight: 190.27
EINECS: 207-616-0
Molar Refractivity: 54.04 cm3
Molar Volume: 153.2 cm3
Density: 1.24 g/cm3
Flash Point: 203.6 °C
Index of Refraction: 1.623
Melting Point: 154-156 °C
Surface Tension: 50.8 dyne/cm
Enthalpy of Vaporization: 66.58 kJ/mol
Boiling Point: 413 °C at 760 mmHg
Vapour Pressure: 4.95E-07 mmHg at 25 °C
Appearance of Cytisine (CAS NO.485-35-8): Off-White to Tan Crystalline Solid
Product Categories of Cytisine (CAS NO.485-35-8): Heterocyclic Compounds; Neurochemicals; Nicotine Derivatives
Canonical SMILES: C1C2CNCC1C3=CC=CC(=O)N3C2
InChI: 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
InChIKey: ANJTVLIZGCUXLD-UHFFFAOYSA-N
Cytisine Uses
Toxic priniciple in seed of Laburnum anagyroides and other Leguminosae. A neuronal nicotinic acetylcholine agonist.
Cytisine Toxicity Data With Reference
| 1. | scu-rat LDLo:20 mg/kg | 85IXA4 Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif Bovet, D., andF. Bovet-Nitti,New York, NY.: S. Karger,1948,589. | ||
| 2. | orl-mus LD50:101 mg/kg | BJPCBM British Journal of Pharmacology. 35 (1969),161. | ||
| 3. | ipr-mus LD50:9400 µg/kg | BJPCBM British Journal of Pharmacology. 35 (1969),161. | ||
| 4. | ivn-mus LD50:1730 µg/kg | BJPCBM British Journal of Pharmacology. 35 (1969),161. | ||
| 5. | inv-cat LD50:400 µg/kg | ITOBAO Izvestiya Akademii Nauk Tadzhikskoi SSR, Otdelenie Biologicheskikh Nauk.(2),(1978),104. |
Cytisine Consensus Reports
Reported in EPA TSCA Inventory.
Cytisine Safety Profile
Poison by ingestion, intravenous and intraperitoneal routes. A toxin found in some plants. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: 
T
Risk Statements: 25-36/37/38
R25 :Toxic if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-28-36/37-45
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S28:After contact with skin, wash immediately with plenty of soap-suds.
S36/37:Wear suitable protective clothing and gloves.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: HA4025000
HazardClass: 6.1(b)
PackingGroup: III
Cytisine Specification
Cytisine , its cas register number 485-35-8. It also can be called (1R,5S)-1,2,3,4,5,6-Hexahydro-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one ; and 1,5-methano-8H-pyrido[1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R,5S)- .
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