524-40-3 Usage
Description
Ricinine, an alkaloid extract from the seeds of the castor-oil plant (Ricinus communis), is a central nervous system stimulant with potential cognitive-enhancing properties. It has been studied for its possible use in treating human amnesias and has demonstrated bactericidal effects on certain pests, as well as heptaprotective activity. Ricinine is a white solid that is neutral in reaction, optically inactive, and forms no normal salts. Its structure has been confirmed through synthesis, and it is not particularly toxic on its own. However, the poisonous character of castor-oil seeds is attributed to a more complex substance called ricin.
Uses
1. Used in Pharmaceutical Applications:
RICININE is used as a potential cognition-enhancing agent for the treatment of human amnesias due to its central nervous system stimulant properties.
2. Used in Antimicrobial Applications:
RICININE is used as a bactericidal agent against three pests, showcasing its potential in the field of antimicrobial research and development.
3. Used in Pest Control:
RICININE is used for its heptaprotective activity, which may have applications in pest control and management.
4. Used in Chemical Research:
RICININE, being a central nervous system stimulant, is used in chemical research to study its potential effects on cognitive functions and the treatment of memory-related disorders.
5. Used in Synthesis and Structural Studies:
RICININE is used in the synthesis of related compounds and for confirming its structure through various chemical reactions and analyses.
Hazard
Toxic by ingestion.
Safety Profile
A poison by ingestion and subcutaneous route. When heated to decomposition it emits toxic vapors of NOx.
References
Tuson.,J. Chern. Soc., 17,195 (1864)
Soave., Chern. Soc. Abstr., i, 386 (1896)
Schultze., ibid, i, 42 (1898)
Evans., J. Arner. Chern. Soc., 22, 39 (1900)
Maqueen, Philippe., Cornpt. rend., 138, 506 (1904)
Maqueen, Philippe., ibid, 139, 840 (1904)
Winterstein, Keller, Weinhagen., Arch. Pharrn., 255,513 (1917)
Bottcher., Ber., 51,673 (1918)
Spath, Tschelnitz., Monatsh., 42,251 (1921)
Spath, Koller., Ber., 56, 880, 2454 (1923)
Spath, Koller., ibid, 58,2124 (1925)
Schroeter et ai., ibid, 65, 432 (1932)
Reitmann., Chern. Abstr., 29,4359 (1935)
Check Digit Verification of cas no
The CAS Registry Mumber 524-40-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,2 and 4 respectively; the second part has 2 digits, 4 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 524-40:
(5*5)+(4*2)+(3*4)+(2*4)+(1*0)=53
53 % 10 = 3
So 524-40-3 is a valid CAS Registry Number.
InChI:InChI=1/C8H8N2O2/c1-10-4-3-7(12-2)6(5-9)8(10)11/h3-4H,1-2H3
524-40-3Relevant articles and documents
Syntheses with Nitriles, LXXII. Ricinine - A Simple Synthesis
Mittelbach, Martin,Kastner, Gabriele,Junek, Hans
, p. 1467 - 1470 (1984)
Cyclization of 1,1-dicyano-4-(N,N-dimethylamino)-2-methoxy-1,3-butadiene leads to 4-methoxy-2(1H)-pyridone-3-carbonitrile and 2,4-dimethoxy-pyridine-3-carbonitrile.Methylation of both products yields ricinine. - Keywords: 4-Methoxy-1-methyl-2(1H)-pyridone-3-carbonitrile; Alkaloid synthesis
A practical procedure for the selective N-alkylation of 4-alkoxy-2-pyridones and its use in a sulfone-mediated synthesis of N-methyl-4-methoxy-2-pyridone
Conreaux, David,Bossharth, Emmanuel,Monteiro, Nuno,Desbordes, Philippe,Balme, Geneviève
, p. 7917 - 7920 (2007/10/03)
It has been found that selective N-alkylation of 4-alkoxy-2-pyridones can be achieved under anhydrous, mild conditions with tetrabutylammonium iodide and potassium tert-butoxide being employed as the catalyst and the base, respectively. The procedure was applied to the preparation of 4-methoxy-1-methyl-2-pyridone, a valuable building block for heterocycle synthesis.
Lithiation of 4-Methoxy-2-pyridones. Synthetic Entry to Tenellin and Funiculosin, and Related Natural 3,5-Disubstituted 4-Oxy-2-pyridones
Buck, Judith,Madeley, J. Paul,Pattenden, Gerald
, p. 67 - 73 (2007/10/02)
Lithiation of 4-methoxy-2-pyridone with butyllithium at -78 deg C occurs at the C-3 position exclusively.Subsequent reactions with MeOD, MeI, CO2, benzaldehyde or (E)-but-2-enal then lead to the corresponding C-3-substituted derivatives. in a one-pot procedure, treatment of 1,2-dihydro-4-methoxy-1-methyl-2-oxopyridine-3-carboxylic acid with ammonia in the presence of a polyphosphate buffer at 80 deg C produced natural ricinine in 58percent overall yield.A convenient three-step synthesis of 5-aryl- and 5-alkyl-substituted 4-methoxy-2-pyridones is described.Lithiation of these substrates, followed by reaction with electrophiles, provided a convenient route to 3,5-disubstituted 4-oxy-2-pyridones, and a synthetic entry to natural products, e. g. tenellin and funiculosin, containing this structural feature.