Ricinine

Last updated
Ricinine
Ricinine.png
Names
Preferred IUPAC name
4-Methoxy-1-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
Other names
3-cyano-4-methoxy-N-methyl-2-pyridone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.601 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-359-7
KEGG
PubChem CID
UNII
  • InChI=1S/C8H8N2O2/c1-10-4-3-7(12-2)6(5-9)8(10)11/h3-4H,1-2H3
    Key: PETSAYFQSGAEQY-UHFFFAOYSA-N
  • Cn1ccc(c(c1=O)C#N)OC
Properties
C8H8N2O2
Molar mass 164.164 g·mol−1
Melting point 200 °C (392 °F; 473 K)
Hazards
Lethal dose or concentration (LD, LC):
340 mg/kg [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Ricinine is a toxic alkaloid found in the castor plant. [2] It can serve as a biomarker of ricin poisoning. [3] [4] It was first isolated from the castor seeds by Tuson in 1864. [5] [6]

Ricinine has insecticidal effects. [7]

It sublimes between 170 and 180 °C at 20 mmHg. It does not form salts, and is precipitated in iodine or mercuric chloride solutions, but not in Mayer's reagent. [5]

It can be hydrolyzed to methanol and ricininic acid by alkali. [5]

See also

References

  1. ↑ Worbs, Sylvia; Köhler, Kernt; Pauly, Diana; Avondet, Marc-André; Schaer, Martin; Dorner, Martin B.; Dorner, Brigitte G. (24 October 2011). "Ricinus communis Intoxications in Human and Veterinary Medicine—A Summary of Real Cases". Toxins. 3 (10): 1332–1372. doi: 10.3390/toxins3101332 . PMC   3210461 . PMID   22069699.
  2. ↑ Peng, Jing; Cai, Shuang; Wang, Lin; Zhao, Nan; Zhang, Ting-jian; Chen, Zai-xing; Meng, Fan-hao; Dzeja, Petras (11 March 2014). "A Metabonomic Analysis of Serum from Rats Treated with Ricinine Using Ultra Performance Liquid Chromatography Coupled with Mass Spectrometry". PLOS ONE. 9 (3) e90416. Bibcode:2014PLoSO...990416P. doi: 10.1371/journal.pone.0090416 . PMC   3949718 . PMID   24618672.
  3. ↑ Hamelin, Elizabeth I.; Johnson, Rudolph C.; Osterloh, John D.; Howard, David J.; Thomas, Jerry D. (November 2012). "Evaluation of Ricinine, a Ricin Biomarker, from a Non-Lethal Castor Bean Ingestion". Journal of Analytical Toxicology. 36 (9): 660–662. doi:10.1093/jat/bks077. PMC   4561852 . PMID   23014889.
  4. ↑ Pittman, C. T.; Guido, J. M.; Hamelin, E. I.; Blake, T. A.; Johnson, R. C. (6 March 2013). "Analysis of a Ricin Biomarker, Ricinine, in 989 Individual Human Urine Samples". Journal of Analytical Toxicology. 37 (4): 237–240. doi:10.1093/jat/bkt010. PMC   4547525 . PMID   23471955.
  5. 1 2 3 Henry, Thomas Anderson (1949). "Ricinine". The Plant Alkaloids (4th ed.). The Blakiston Company. p. 5.
  6. ↑ Rao, N. V. Subra (Feb 12, 1945). "A Note on the Chemical Composition of Castor Leaves" . Proceedings of the Indian Academy of Sciences. A (21): 123–125. doi:10.1007/BF03051280. S2CID   94199266 . Retrieved Aug 7, 2021.
  7. ↑ Wachira, Sabina; Omar, Sabar; Jacob, Julia; Wahome, Martin; Alborn, Hans T; Spring, David R; Masiga, Daniel K; Torto, Baldwyn (2014). "Toxicity of six plant extracts and two pyridone alkaloids from Ricinus communis against the malaria vector Anopheles gambiae". Parasites & Vectors. 7 (1): 312. doi: 10.1186/1756-3305-7-312 . PMC   4098926 . PMID   24996560.
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