Ricinine

Base Information

• Chemical Name: Ricinine
• CAS No.: 524-40-3
• Molecular Formula: C8H8 N2 O2
• Molecular Weight: 164.164
• Hs Code.: 2933399090
• European Community (EC) Number: 208-359-7
• NSC Number: 642604,409913
• UNII: 130UFS7AE0
• DSSTox Substance ID: DTXSID50200412
• Nikkaji Number: J89.951H
• Wikipedia: Ricinine
• Wikidata: Q907865
• Metabolomics Workbench ID: 49689
• ChEMBL ID: CHEMBL1329957
• Mol file: 524-40-3.mol

Synonyms:3-cyano-4-methoxy-N-methyl-2-pyridone;ricinine

Chemical Property of Ricinine

Chemical Property:

• Vapor Pressure: 1.07E-05mmHg at 25°C
• Melting Point: 200-201 °C.
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 370.9 °C at 760 mmHg
• PKA: -4.93±0.62(Predicted)
• Flash Point: 178.1 °C
• PSA: 55.02000
• Density: 1.23 g/cm³
• LogP: 0.26558
• Storage Temp.: ?20°C
• Water Solubility.: 2.7g/L(10 oC)
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 164.058577502
• Heavy Atom Count: 12
• Complexity: 319

Purity/Quality:

99% ^*data from raw suppliers

Ricinine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A poison by ingestion.
• Hazard Codes: T,Xn,F
• Statements: 25-36-20/21/22-11
• Safety Statements: 45-36/37-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=CC(=C(C1=O)C#N)OC
• Description: First isolated by Tuson from the seeds of Ricinus communis (castor-oil seed), the alkaloid was subsequently examined by Soave, Schultze and Evans. The base crystallizes from H20 in colourless prisms or leaflets and sublimes at 170-lS0°C/ 20 mm. It is soluble in hot H20 or CHCI3, only sparingly so in EtOH and insoluble in petroleum ether, is neutral in reaction, optically inactive and forms no normal salts although the mercurichloride, m.p. 204°C has been prepared. The alkaloid reduces KMn04 and may be hydrolyzed by alkalies to MeOH and ricininic acid which forms brilliant, slender needles, m.p. 296-8°C (dec.). The structure of ricinine has been confirmed by synthesis from 4-chloroquinoline. Other syntheses have also been achieved. The base is not particularly toxic and the poisonous character of castor-oil seeds has been shown to be due to a more complex substance, ricin, the toxicity of which may be destroyed by heating.
• Uses: An alkaloid extract from the seeds of the castor-oil plant (Ricinus communalis). It is a central nervous system stimulant that could potentially be a cognition-enhancing agent used for the treatment of human amnesias. It also has bactericidal effects on t Ricinine is an alkaloid extract from the seeds of the castor-oil plant (Ricinus communalis). Ricinine is a central nervous system stimulant that could potentially be a cognition-enhancing agent used for the treatment of human amnesias. Ricinine also has bactericidal effects on three pests and heptaprotective activity.

Technology Process of Ricinine

There total 16 articles about Ricinine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile (21642-98-8) + methyl iodide (74-88-4) → ricinin (524-40-3)

Guidance literature:

4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile; With potassium tert-butylate; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 0 ℃;

methyl iodide; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.tetlet.2005.09.095

Reference yield: 70.0%

2,4-Dimethoxy-pyridin-3-carbonitril (95689-37-5) → ricinin (524-40-3)

Guidance literature:

With methyl iodide; at 130 ℃; for 6h;

DOI:10.1007/BF00816346

Reference yield: 56.0%

1,2-dihydro-4-methoxy-1-methyl-2-oxopyridine-3-carboxylic acid (16803-45-5) → ricinin (524-40-3)

Guidance literature:

With ethylpolyphosphate; ammonia; In chloroform; 1a) 2 h, b) 80 deg C, 4 h;

upstream raw materials:

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

4-methoxypyridine-3-carbonitrile

2,4-Dimethoxy-pyridin-3-carbonitril

methyl iodide

Downstream raw materials:

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

hydrogen cyanide

succinic acid

ammonia

Refernces

• 1、 Li, Jing,Tan, Hong-Ru,An, Yu-Long,Shao, Zhi-Yu,Zhao, Sheng-Yin. "Synthesis and DABCO-induced demethylation of 3-cyano-4-methoxy-2-pyridone derivatives". . p. 486 - 496. Retrieved 2019/12/24.
• 2、 Yuldashev. "Ricinine and its transformations". . p. 274 - 275. Retrieved 2007/10/03.