Product Name

  • Name

    Cytisine

  • EINECS 207-616-0
  • CAS No. 485-35-8
  • Article Data9
  • CAS DataBase
  • Density 1.24 g/cm3
  • 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
  • Appearance Off-white to tan crystalline solid
  • Safety 26-28-36/37-45
  • Risk Codes 25-36/37/38
  • Molecular Structure Molecular Structure of 485-35-8 (Cytisine)
  • Hazard Symbols ToxicT
  • 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)-;
  • PSA 34.03000
  • LogP 0.88380

Synthetic route

(6R,7R,9R)-(-)-N-benzyloxycarbonyl-cytisine
667940-15-0

(6R,7R,9R)-(-)-N-benzyloxycarbonyl-cytisine

cytisine
485-35-8

cytisine

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran for 3h; Heating;78%
N-nosyl-(−)-cytisine

N-nosyl-(−)-cytisine

cytisine
485-35-8

cytisine

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

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

cytisine
485-35-8

cytisine

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%
(3S,5R)-(+)-3-acetoxymethyl-5-formyl-1-piperidine-1-carbvoxylic acid benzyl ester
206554-22-5

(3S,5R)-(+)-3-acetoxymethyl-5-formyl-1-piperidine-1-carbvoxylic acid benzyl ester

cytisine
485-35-8

cytisine

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
(3S,5R)-3-acetoxymethyl-5-hydroxymethylpiperidine-1-carboxylic acid benzyl ester
206761-38-8

(3S,5R)-3-acetoxymethyl-5-hydroxymethylpiperidine-1-carboxylic acid benzyl ester

cytisine
485-35-8

cytisine

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
(3S,5R,1'S)-(-)-3-acetoxymethyl-5-(1'-hydroxybut-3'-enyl)-1-piperidine-1-carboxylic acid benzyl ester
667940-16-1

(3S,5R,1'S)-(-)-3-acetoxymethyl-5-(1'-hydroxybut-3'-enyl)-1-piperidine-1-carboxylic acid benzyl ester

cytisine
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
(3S,5R,1'R)-(-)-3-acetoxymethyl-5-(1'-azidobut-3'-enyl)-1-piperidine-1-carboxylic acid benzyl ester
667940-11-6

(3S,5R,1'R)-(-)-3-acetoxymethyl-5-(1'-azidobut-3'-enyl)-1-piperidine-1-carboxylic acid benzyl ester

cytisine
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
(3S,5R)-3-Acetoxymethyl-5-((R)-1-amino-but-3-enyl)-piperidine-1-carboxylic acid benzyl ester
667940-18-3

(3S,5R)-3-Acetoxymethyl-5-((R)-1-amino-but-3-enyl)-piperidine-1-carboxylic acid benzyl ester

cytisine
485-35-8

cytisine

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
(3S,5R,1'S)-(+)-3-acetoxymethyl-5-(1'-methanesulfonyloxybut-3'-enyl)-1-piperidine-1-carboxylic acid benzyl ester
667940-10-5

(3S,5R,1'S)-(+)-3-acetoxymethyl-5-(1'-methanesulfonyloxybut-3'-enyl)-1-piperidine-1-carboxylic acid benzyl ester

cytisine
485-35-8

cytisine

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
(3S,5R,1'R)-(+)-3-acetoxymethyl-5-(1'-acryloylaminobut-3'-enyl)-1-piperidine-1-carboxylic acid benzyl ester
667940-08-1

(3S,5R,1'R)-(+)-3-acetoxymethyl-5-(1'-acryloylaminobut-3'-enyl)-1-piperidine-1-carboxylic acid benzyl ester

cytisine
485-35-8

cytisine

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
1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one
485-35-8, 15191-27-2, 55821-72-2

1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one

cytisine
485-35-8

cytisine

Conditions
ConditionsYield
With camphor-10-sulfonic acid
(6R,7R,9R)-(+)-N-benzyloxycarbonyl-5,6-dihydro-cytisine
667940-14-9

(6R,7R,9R)-(+)-N-benzyloxycarbonyl-5,6-dihydro-cytisine

cytisine
485-35-8

cytisine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 50 percent / DDQ / dioxane / 4 h / 110 °C
2: 78 percent / HCl / tetrahydrofuran / 3 h / Heating
View Scheme
(2R,3'R,5'S)-(+)-5-hydroxymethyl-6-oxo-1,2,3,6,3',4',5',6'-octahydro-2'H-[2,3']-bipyridinyl-1'-carboxylic acid benzyl ester
667940-12-7

(2R,3'R,5'S)-(+)-5-hydroxymethyl-6-oxo-1,2,3,6,3',4',5',6'-octahydro-2'H-[2,3']-bipyridinyl-1'-carboxylic acid benzyl ester

cytisine
485-35-8

cytisine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 67 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C
2: 89 percent / NaH / tetrahydrofuran / 0 - 20 °C
3: 50 percent / DDQ / dioxane / 4 h / 110 °C
4: 78 percent / HCl / tetrahydrofuran / 3 h / Heating
View Scheme
(2R,3'R,5'S)-(+)-5-acetoxymethyl-6-oxo-1,2,3,6,3',4',5',6'-octahydro-2'H-[2,3']-bipyridinyl-1'-carboxylic acid benzyl ester
667940-07-0

(2R,3'R,5'S)-(+)-5-acetoxymethyl-6-oxo-1,2,3,6,3',4',5',6'-octahydro-2'H-[2,3']-bipyridinyl-1'-carboxylic acid benzyl ester

cytisine
485-35-8

cytisine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 98 percent / NaOH / tetrahydrofuran / 2 h / 20 °C
2: 67 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C
3: 89 percent / NaH / tetrahydrofuran / 0 - 20 °C
4: 50 percent / DDQ / dioxane / 4 h / 110 °C
5: 78 percent / HCl / tetrahydrofuran / 3 h / Heating
View Scheme
(2R,3'R,5'S)-(+)-5-methanesulfonyloxymethyl-6-oxo-1,2,3,6,3',4',5',6'-octahydro-2'H-[2,3']-bipyridinyl-1'-carboxylic acid benzyl ester
667940-13-8

(2R,3'R,5'S)-(+)-5-methanesulfonyloxymethyl-6-oxo-1,2,3,6,3',4',5',6'-octahydro-2'H-[2,3']-bipyridinyl-1'-carboxylic acid benzyl ester

cytisine
485-35-8

cytisine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 89 percent / NaH / tetrahydrofuran / 0 - 20 °C
2: 50 percent / DDQ / dioxane / 4 h / 110 °C
3: 78 percent / HCl / tetrahydrofuran / 3 h / Heating
View Scheme
(1R,5R)-6-methyl-3,7-diazabicyclo[3.3.1]non-6-en-2-one

(1R,5R)-6-methyl-3,7-diazabicyclo[3.3.1]non-6-en-2-one

cytisine
485-35-8

cytisine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: triethylamine; dmap / dichloromethane / 20 h
2.1: triethylamine / tetrahydrofuran / 5 h / 20 °C
3.1: methanol; sodium tetrahydroborate / 2 h / 0 - 20 °C
3.2: 15 h / -78 - 20 °C
View Scheme
(1R,5R)-3-tert-butoxycarbonyl-6-methyl-3,7-diazabicyclo[3.3.1]non-6-en-2-one

(1R,5R)-3-tert-butoxycarbonyl-6-methyl-3,7-diazabicyclo[3.3.1]non-6-en-2-one

cytisine
485-35-8

cytisine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / tetrahydrofuran / 5 h / 20 °C
2.1: methanol; sodium tetrahydroborate / 2 h / 0 - 20 °C
2.2: 15 h / -78 - 20 °C
View Scheme
methyl 5-(6-bromopyridin-2-yl)-1-tosylpiperidine-3-carboxylate

methyl 5-(6-bromopyridin-2-yl)-1-tosylpiperidine-3-carboxylate

cytisine
485-35-8

cytisine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C
2.1: triethylamine / dichloromethane / 1 h / 0 °C
3.1: chloroform / 6.5 h / Reflux
3.2: 9 h / 23 °C
4.1: thiophenol; potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 0.5 h / 45 °C
View Scheme
(5-(6-bromopyridin-2-yl)-1-tosylpiperidin-3-yl)methanol

(5-(6-bromopyridin-2-yl)-1-tosylpiperidin-3-yl)methanol

cytisine
485-35-8

cytisine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: triethylamine / dichloromethane / 1 h / 0 °C
2.1: chloroform / 6.5 h / Reflux
2.2: 9 h / 23 °C
3.1: thiophenol; potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 0.5 h / 45 °C
View Scheme
C19H23BrN2O5S2

C19H23BrN2O5S2

cytisine
485-35-8

cytisine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: chloroform / 6.5 h / Reflux
1.2: 9 h / 23 °C
2.1: thiophenol; potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 0.5 h / 45 °C
View Scheme
cytisine
485-35-8

cytisine

Nitrosocytisine
19634-60-7

Nitrosocytisine

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite at 20℃; for 288h; Nitrosation;100%
With potassiuim nitrosodisulfonate; hydroxylamine hydrochloride; sodium carbonate In pyridine for 0.25h;91%
acetic anhydride
108-24-7

acetic anhydride

cytisine
485-35-8

cytisine

(-)-(1R,5S)-N-acetyl-1,2,3,4,5,6-hexahydro-1,5-methano-pyrido-[1,2-a][1,5]diazocin-8-one
6018-52-6

(-)-(1R,5S)-N-acetyl-1,2,3,4,5,6-hexahydro-1,5-methano-pyrido-[1,2-a][1,5]diazocin-8-one

Conditions
ConditionsYield
With dmap In pyridine at 20℃; for 12h; Acetylation;100%
88.4%
1-adamantyl isocyanate
4411-25-0

1-adamantyl isocyanate

cytisine
485-35-8

cytisine

N-1-adamantylcytisine-12-carbamide

N-1-adamantylcytisine-12-carbamide

Conditions
ConditionsYield
In benzene at 80℃;100%
1-adamantylisothiocyanate
4411-26-1

1-adamantylisothiocyanate

cytisine
485-35-8

cytisine

N-1-adamantylcytisine-12-thiocarbamide
1621257-20-2

N-1-adamantylcytisine-12-thiocarbamide

Conditions
ConditionsYield
In benzene at 80℃;100%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

cytisine
485-35-8

cytisine

8-oxo-1,5,6,8-tetrahydro-2H,4H-1,5-methano-pyrido[1,2-a][1,5]diazocine-3-carboxylic acid tert-butyl ester [N-tboccytisine]
207390-62-3

8-oxo-1,5,6,8-tetrahydro-2H,4H-1,5-methano-pyrido[1,2-a][1,5]diazocine-3-carboxylic acid tert-butyl ester [N-tboccytisine]

Conditions
ConditionsYield
With sodium carbonate In tetrahydrofuran; water at 20℃; for 48h;99%
With sodium carbonate In tetrahydrofuran at 20℃; for 24h;96%
With sodium carbonate In tetrahydrofuran; water for 72h;93%
benzyl bromide
100-39-0

benzyl bromide

cytisine
485-35-8

cytisine

(1R,9S)-11-benzyl-7,11-diazatricyclo[7.3.1.0]trideca-2,4-dien-6-one
78867-61-5, 109667-42-7

(1R,9S)-11-benzyl-7,11-diazatricyclo[7.3.1.0]trideca-2,4-dien-6-one

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 20h; Reflux;99%
With potassium carbonate In acetonitrile for 5h; Heating;94%
With potassium carbonate In acetonitrile for 5h; Reflux; Inert atmosphere;94%
With sodium carbonate In dichloromethane; water for 4h; Heating;77%
thiourea
17356-08-0

thiourea

cytisine
485-35-8

cytisine

N-cytisine-12-thiocarbamide
1401073-44-6

N-cytisine-12-thiocarbamide

Conditions
ConditionsYield
In pentan-1-ol at 137℃;98%
allylisocyanate
1476-23-9

allylisocyanate

cytisine
485-35-8

cytisine

N-allylcytisine-11-carbamide
449797-68-6

N-allylcytisine-11-carbamide

Conditions
ConditionsYield
In benzene at 20℃;98%
phenyl isocyanate
103-71-9

phenyl isocyanate

cytisine
485-35-8

cytisine

N-phenylcytisine-11-carbamide
40705-13-3

N-phenylcytisine-11-carbamide

Conditions
ConditionsYield
In benzene at 20℃;98%
di(4-isocyanatophenyl)methane
101-68-8

di(4-isocyanatophenyl)methane

cytisine
485-35-8

cytisine

N,N'-[methylene-bis(4,1-phenylene)]dicytisinecarboxamide
1620659-65-5

N,N'-[methylene-bis(4,1-phenylene)]dicytisinecarboxamide

Conditions
ConditionsYield
In benzene at 80℃;98%
2-(4-phenoxybutyl)oxirane
85234-59-9

2-(4-phenoxybutyl)oxirane

cytisine
485-35-8

cytisine

(1R,2'ζ,5S)-3-(2-hydroxy-6-phenoxyhexyl)-3,4,5,6-tetrahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-8(2H)-one

(1R,2'ζ,5S)-3-(2-hydroxy-6-phenoxyhexyl)-3,4,5,6-tetrahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-8(2H)-one

Conditions
ConditionsYield
In methanol at 90℃; for 8h;98%
formaldehyd
50-00-0

formaldehyd

Ethyl isocyanoacetate
2999-46-4

Ethyl isocyanoacetate

cytisine
485-35-8

cytisine

ethyl 2-(5-(((1R,5S)-8-oxo-5,6-dihydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-3(2H,4H,8H)-yl)methyl)-1H-tetrazol-1-yl)acetate

ethyl 2-(5-(((1R,5S)-8-oxo-5,6-dihydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-3(2H,4H,8H)-yl)methyl)-1H-tetrazol-1-yl)acetate

Conditions
ConditionsYield
With trimethylsilylazide In methanol at 20℃; for 24h; Ugi Condensation;98%
...Expand
formaldehyd
50-00-0

formaldehyd

cytisine
485-35-8

cytisine

methyl 3-isocyanopropanoate

methyl 3-isocyanopropanoate

methyl 3-(5-(((1R,5S)-8-oxo-5,6-dihydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-3(2H,4H,8H)-yl)methyl)-1H-tetrazol-1-yl)propanoate

methyl 3-(5-(((1R,5S)-8-oxo-5,6-dihydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-3(2H,4H,8H)-yl)methyl)-1H-tetrazol-1-yl)propanoate

Conditions
ConditionsYield
With trimethylsilylazide In methanol at 20℃; for 24h; Ugi Condensation;98%
...Expand
Methoxyacetyl chloride
38870-89-2

Methoxyacetyl chloride

cytisine
485-35-8

cytisine

(1R,5S)-N-(2-methoxyacetyl)-1,2,3,4,5,6-hexahydro-1,5-methanopyrido[1,2-a]diazocin-8-one
881853-39-0

(1R,5S)-N-(2-methoxyacetyl)-1,2,3,4,5,6-hexahydro-1,5-methanopyrido[1,2-a]diazocin-8-one

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 18h;97%
3,5-dichlorobenzoyl chloride
2905-62-6

3,5-dichlorobenzoyl chloride

cytisine
485-35-8

cytisine

(1R,5S)-3-(3,5-Dichloro-benzoyl)-1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one

(1R,5S)-3-(3,5-Dichloro-benzoyl)-1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one

Conditions
ConditionsYield
With triethylamine In acetone Acylation; Heating;96%
propionyl chloride
79-03-8

propionyl chloride

cytisine
485-35-8

cytisine

(1R,5S)-3-propionyl-3,4,5,6-tetrahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-8(2H)-one
474116-07-9

(1R,5S)-3-propionyl-3,4,5,6-tetrahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-8(2H)-one

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;96%
With triethylamine In dichloromethane at 0 - 22℃; for 3h;12.3 g
N-allyl isothiocyanate
57-06-7

N-allyl isothiocyanate

cytisine
485-35-8

cytisine

cytisino-N-allylthiocarbamide
945421-04-5

cytisino-N-allylthiocarbamide

Conditions
ConditionsYield
In benzene at 35 - 40℃;96%
1,1-bis(diethylphosphono)ethylene
37465-31-9

1,1-bis(diethylphosphono)ethylene

cytisine
485-35-8

cytisine

C13H20N2O7P2*BrH

C13H20N2O7P2*BrH

Conditions
ConditionsYield
In chloroform at 20℃; for 72h;96%
3-(4-chlorophenyl)-2-methyl-7-(4-(oxiran-2-yl)butoxy)-4H-chromen-4-one

3-(4-chlorophenyl)-2-methyl-7-(4-(oxiran-2-yl)butoxy)-4H-chromen-4-one

cytisine
485-35-8

cytisine

(1R,2’ζ,5S)-3-(6-((3-(4-chlorophenyl)-2-methyl-4-oxo-4H-chromen-7-yl)oxy)-2-hydroxyhexyl)-3,4,5,6-tetrahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-8(2H)-one

(1R,2’ζ,5S)-3-(6-((3-(4-chlorophenyl)-2-methyl-4-oxo-4H-chromen-7-yl)oxy)-2-hydroxyhexyl)-3,4,5,6-tetrahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-8(2H)-one

Conditions
ConditionsYield
In ethanol at 90℃; for 20h;96%
In ethanol at 90℃; for 20h;96%
cytisine
485-35-8

cytisine

formic acid ethyl ester
109-94-4

formic acid ethyl ester

(1R,5S)-8-oxo-1,5,6,8-tetrahydro-2H-1,5-methanopyrido[1,2-a][1,5]diazocine-3(4H)-carbaldehyde
53007-06-0

(1R,5S)-8-oxo-1,5,6,8-tetrahydro-2H-1,5-methanopyrido[1,2-a][1,5]diazocine-3(4H)-carbaldehyde

Conditions
ConditionsYield
With triethylamine for 19h; Reflux;96%
tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

pentan-3-one
96-22-0

pentan-3-one

cytisine
485-35-8

cytisine

(1R,5S)-3-(3-(1-(tert-butyl)-1H-tetrazol-5-yl)pentan-3-yl)-3,4,5,6-tetrahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-8(2H)-one

(1R,5S)-3-(3-(1-(tert-butyl)-1H-tetrazol-5-yl)pentan-3-yl)-3,4,5,6-tetrahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-8(2H)-one

Conditions
ConditionsYield
With trimethylsilylazide In methanol at 20℃; for 24h; Ugi Condensation;96%
...Expand

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: 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

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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