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485-35-8

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Basic Information
CAS No.: 485-35-8
Name: Cytisine
Article Data: 9
Molecular Structure:
Molecular Structure of 485-35-8 (Cytisine)
Formula: C11H14N2O
Molecular Weight: 190.245
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)-;
EINECS: 207-616-0
Density: 1.24 g/cm3
Melting Point: 154-156 °C(lit.)
Boiling Point: 413 °C at 760 mmHg
Flash Point: 203.6 °C
Solubility: Soluble to 100 mM in Water
Appearance: Off-white to tan crystalline solid
Hazard Symbols: ToxicT
Risk Codes: 25-36/37/38
Safety: 26-28-36/37-45
PSA: 34.03000
LogP: 0.88380
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Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran for 3h; Heating;78%

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Conditions
ConditionsYield
With potassium carbonate; thiophenol In N,N-dimethyl-formamide; acetonitrile at 45℃; for 0.5h;96%

(1R,9R)-11-tert-butoxycarbonyl-7,11-diazatricyclo[7.3.1.02,7]tridec-2,4-dien-6,10-dione

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Conditions
ConditionsYield
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

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Conditions
ConditionsYield
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

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Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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

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Conditions
ConditionsYield
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

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Conditions
ConditionsYield
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

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Conditions
ConditionsYield
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
Raw Materials
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667940-18-3
667940-07-0
485-35-8
667940-10-5
667940-11-6
667940-08-1
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Chemistry

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

Uses

Toxic priniciple in seed of Laburnum anagyroides and other Leguminosae. A neuronal nicotinic acetylcholine agonist.

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.

Consensus Reports

Reported in EPA TSCA Inventory.

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: ToxicT
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

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)- .