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Ricinine

Summary

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
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
  • 524-40-3
3D model (JSmol)
  • Interactive image
3DMet
  • B00311
ChEBI
  • CHEBI:18043
ChEMBL
  • ChEMBL1329957
ChemSpider
  • 10216
ECHA InfoCard 100.007.601 Edit this at Wikidata
EC Number
  • 208-359-7
KEGG
  • C01526
  • 10666
UNII
  • 130UFS7AE0
  • DTXSID50200412 Edit this at Wikidata
  • 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).
Infobox references

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 edit

References edit

  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. ^ a b c 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.