Product Name

  • Name

    RICININE

  • EINECS 208-359-7
  • CAS No. 524-40-3
  • Article Data14
  • CAS DataBase
  • Density 1.23 g/cm3
  • Solubility soluble in water? methanol and ethanol; less in organic solvents
  • Melting Point 200-201 °C.
  • Formula C8H8 N2 O2
  • Boiling Point 370.9 °C at 760 mmHg
  • Molecular Weight 164.164
  • Flash Point 178.1 °C
  • Transport Information
  • Appearance
  • Safety A poison by ingestion and subcutaneous route. When heated to decomposition it emits toxic vapors of NOx.
  • Risk Codes 25-36-20/21/22-11
  • Molecular Structure Molecular Structure of 524-40-3 (RICININE)
  • Hazard Symbols A poison by ingestion.
  • Synonyms Nicotinonitrile,1,2-dihydro-4-methoxy-1-methyl-2-oxo- (7CI,8CI); Ricinine (6CI);1,2-Dihydro-4-methoxy-1-methyl-2-oxonicotinonitrile; NSC 409913; NSC 642604;Recinine; Ricinin
  • PSA 55.02000
  • LogP 0.26558

Synthetic route

4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile
21642-98-8

4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile

methyl iodide
74-88-4

methyl iodide

ricinin
524-40-3

ricinin

Conditions
ConditionsYield
Stage #1: 4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile With potassium tert-butylate; tetra-(n-butyl)ammonium iodide In tetrahydrofuran at 0℃;
Stage #2: methyl iodide In tetrahydrofuran at 20℃;		90%
With potassium carbonate In acetonitrile for 10h; Reflux;78%
2,4-Dimethoxy-pyridin-3-carbonitril
95689-37-5

2,4-Dimethoxy-pyridin-3-carbonitril

ricinin
524-40-3

ricinin

Conditions
ConditionsYield
With methyl iodide at 130℃; for 6h;70%
With methyl iodide at 155℃;
1,2-dihydro-4-methoxy-1-methyl-2-oxopyridine-3-carboxylic acid
16803-45-5

1,2-dihydro-4-methoxy-1-methyl-2-oxopyridine-3-carboxylic acid

ricinin
524-40-3

ricinin

Conditions
ConditionsYield
With ethylpolyphosphate; ammonia In chloroform 1a) 2 h, b) 80 deg C, 4 h;56%
4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile
21642-98-8

4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile

dimethyl sulfate
77-78-1

dimethyl sulfate

ricinin
524-40-3

ricinin

Conditions
ConditionsYield
With sodium hydroxide at 0℃;53%
2-Chloro-5-cyano-4-methoxy-N-methylpyrid-6-one
93769-12-1

2-Chloro-5-cyano-4-methoxy-N-methylpyrid-6-one

ricinin
524-40-3

ricinin

Conditions
ConditionsYield
With sulfuric acid; zinc
4-methoxypyridine-3-carbonitrile
74133-20-3

4-methoxypyridine-3-carbonitrile

ricinin
524-40-3

ricinin

Conditions
ConditionsYield
With dimethyl sulfate; benzene Behandeln des Reaktionsprodukts mit K3 in H2O;
2,4-Dimethoxy-pyridin-3-carbonitril
95689-37-5

2,4-Dimethoxy-pyridin-3-carbonitril

methyl iodide
74-88-4

methyl iodide

ricinin
524-40-3

ricinin

Conditions
ConditionsYield
at 120 - 130℃;
at 120 - 130℃; im Vakuum;
at 120 - 130℃; im Rohr;
chloroform
67-66-3

chloroform

1-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyridine-3-carbonitrile; silver salt

1-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyridine-3-carbonitrile; silver salt

methyl iodide
74-88-4

methyl iodide

ricinin
524-40-3

ricinin

...Expand
methyl iodide
74-88-4

methyl iodide

silver salt of/the/ ricininic acid

silver salt of/the/ ricininic acid

ricinin
524-40-3

ricinin

Conditions
ConditionsYield
With chloroform
sodium-compound of/the/ ricininic acid

sodium-compound of/the/ ricininic acid

ricinin
524-40-3

ricinin

Conditions
ConditionsYield
With methyl bromide at 100℃;
With dimethyl sulfate; xylene
4-chloro-3-cyano-1-methylpyridin-2(1H)-one
62617-49-6

4-chloro-3-cyano-1-methylpyridin-2(1H)-one

sodium methylate
124-41-4

sodium methylate

A

ricinin
524-40-3

ricinin

B

ricininic acid

ricininic acid

...Expand
diazomethane
186581-53-3, 908094-01-9

diazomethane

4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
520-78-5

4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

ricinin
524-40-3

ricinin

Conditions
ConditionsYield
In methanol; diethyl ether for 48h;120 mg
1,1-Dicyan-4-(N,N-dimethylamino)-2-methoxybutadien-1,3
95689-38-6

1,1-Dicyan-4-(N,N-dimethylamino)-2-methoxybutadien-1,3

ricinin
524-40-3

ricinin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 87 percent / methanol / 15 h / Heating
2: 70 percent / CH3I / 6 h / 130 °C
View Scheme
4-methoxy-1-methyl-2-pyridone
41759-19-7

4-methoxy-1-methyl-2-pyridone

ricinin
524-40-3

ricinin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) BuLi / 1) THF, hexane, -78 deg C, 30 min, 2a) -78 deg C, 15 min
2: 56 percent / ethylpolyphosphate, NH3(g) / CHCl3 / 1a) 2 h, b) 80 deg C, 4 h
View Scheme
4-hydroxy-2-pyridone
626-03-9

4-hydroxy-2-pyridone

ricinin
524-40-3

ricinin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 50 percent / 40percent aq. NaOH, triethylbenzylammonium bromide / benzene / 96 h / 70 °C
2: 1) BuLi / 1) THF, hexane, -78 deg C, 30 min, 2a) -78 deg C, 15 min
3: 56 percent / ethylpolyphosphate, NH3(g) / CHCl3 / 1a) 2 h, b) 80 deg C, 4 h
View Scheme
ricinin
524-40-3

ricinin

4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
520-78-5

4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 90℃; for 6h; Green chemistry; chemoselective reaction;92%
With water; sodium hydroxide In tetrahydrofuran at 110℃; for 2h;87.5%
With sodium hydroxide In water for 0.333333h;
With sodium hydroxide for 0.5h; Heating;0.31 g
ricinin
524-40-3

ricinin

5-bromo-4-methoxy-1-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

5-bromo-4-methoxy-1-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

Conditions
ConditionsYield
With N-Bromosuccinimide; trifluoroacetic acid In acetonitrile for 8h; Reflux;81%
With bromine In dichloromethane at 60℃; for 48h;47.3%
With bromine In dichloromethane at 60℃; for 48h;
ricinin
524-40-3

ricinin

4-methoxy-1-methyl-2-oxo-1,2-dihydropyridine-3-carbonamide

4-methoxy-1-methyl-2-oxo-1,2-dihydropyridine-3-carbonamide

Conditions
ConditionsYield
With sulfuric acid at 80 - 90℃; for 6h;72%
With polyphosphoric acid at 110℃; for 2h;43.6%
ricinin
524-40-3

ricinin

pyridine
110-86-1

pyridine

Conditions
ConditionsYield
bei der Zinkstaub-Destillation;
ricinin
524-40-3

ricinin

2-Chloro-5-cyano-4-methoxy-N-methylpyrid-6-one
93769-12-1

2-Chloro-5-cyano-4-methoxy-N-methylpyrid-6-one

Conditions
ConditionsYield
With chlorine; acetic acid
ricinin
524-40-3

ricinin

1-methyl-1H-pyridine-2,4-dione
856956-19-9

1-methyl-1H-pyridine-2,4-dione

Conditions
ConditionsYield
With hydrogenchloride at 140℃;
ricinin
524-40-3

ricinin

4-methoxy-1-methyl-2-pyridone
41759-19-7

4-methoxy-1-methyl-2-pyridone

Conditions
ConditionsYield
With sulfuric acid
ricinin
524-40-3

ricinin

1-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyridine-3-carbonitrile

1-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyridine-3-carbonitrile

Conditions
ConditionsYield
With aqueous alkali
With potassium hydroxide
With potassium carbonate
ricinin
524-40-3

ricinin

6-bromo-4-methoxy-1-methyl-2-oxo-1,2-dihydro-pyridine-3-carbonitrile

6-bromo-4-methoxy-1-methyl-2-oxo-1,2-dihydro-pyridine-3-carbonitrile

Conditions
ConditionsYield
With water; bromine
With chloroform; bromine
ricinin
524-40-3

ricinin

4-methoxy-1-methyl-2-oxo-piperidine-3-carbonitrile; hydrochloride

4-methoxy-1-methyl-2-oxo-piperidine-3-carbonitrile; hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; platinum
ricinin
524-40-3

ricinin

zinc dust

zinc dust

α.γ-dipyridyl

α.γ-dipyridyl

Conditions
ConditionsYield
beim Erhitzen auf Dunkelrotglut;
hydrogenchloride
7647-01-0

hydrogenchloride

ricinin
524-40-3

ricinin

1-methyl-1H-pyridine-2,4-dione
856956-19-9

1-methyl-1H-pyridine-2,4-dione

Conditions
ConditionsYield
at 140℃; im Rohr;
ricinin
524-40-3

ricinin

sulfuric acid
7664-93-9

sulfuric acid

1-methyl-4-methoxy-pyridone-(2)

1-methyl-4-methoxy-pyridone-(2)

ricinin
524-40-3

ricinin

water
7732-18-5

water

barium permanganate

barium permanganate

A

hydrogen cyanide
74-90-8

hydrogen cyanide

B

succinic acid
110-15-6

succinic acid

C

ammonia
7664-41-7

ammonia

D

oxalic acid
144-62-7

oxalic acid

...Expand
ricinin
524-40-3

ricinin

chloroform
67-66-3

chloroform

bromine
7726-95-6

bromine

bromoricinine

bromoricinine

...Expand
ricinin
524-40-3

ricinin

water
7732-18-5

water

bromine
7726-95-6

bromine

bromoricinine

bromoricinine

...Expand
ricinin
524-40-3

ricinin

chlorine
7782-50-5

chlorine

acetic acid
64-19-7

acetic acid

chlororicinine

chlororicinine

...Expand
ricinin
524-40-3

ricinin

alkali

alkali

A

methanol
67-56-1

methanol

B

ricininic acid

ricininic acid

...Expand

RICININ Chemical Properties

Molecular Formula:C8H8N2O2
Molecular Weight:164.18
EINECS:208-359-7
Density:1.23 g/cm3
Melting Point:200-201 °C.
Boiling Point:370.9 °C at 760 mmHg
Flash Point:178.1 °C
Solubility:soluble in water, methanol and ethanol; less in organic solvents
Ricinin's Synonyms: RICININE;1,2-dihydro-4-methoxy-1-methyl-2-oxo-3-pyridinecarbonitril;1,2-dihydro-4-methoxy-1-methyl-2-oxo-nicotinonitril;1,2-dihydro-4-methoxy-1-methyl-2-oxonicotinonitrile;recinine;ricinin;NICOTINONITRILE,1,2-DIHYDRO-4-METHYL-2-OXO-;1,2-Dihydro-4-methoxy-1-methyl-2-oxo-3-pyridinecarbonitrile

RICININ Toxicity Data With Reference

1.   

orl-rat LDLo:75 mg/kg

   NCNSA6    National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. 5 (1953),23.
2.   

scu-mus LD50:25 mg/kg

   PBBHAU    Pharmacology, Biochemistry and Behavior. 63 (1999),367.

RICININ Safety Profile

A poison by ingestion and subcutaneous route. When heated to decomposition it emits toxic vapors of NOx.

RICININ Specification

Ricinin is a bitter white crystalline alkaloid (C8H8N2O2) extracted from the seeds of the castor-oil plant. Ingestion may cause vomiting and various other toxic reactions, including liver and kidney damage, convulsions, hypotension, and death

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