Ricinine

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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.601 Edit this at Wikidata
EC Number
  • 208-359-7
KEGG
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
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. It can serve as a biomarker of ricin poisoning. It was first isolated from the castor seeds by Tuson in 1864. Compared to ricin, it is very poorly studied, since unlike ricin, ricinine has essentially no biological effect on humans.

Ricinine has insecticidal effects.

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.

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

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. ↑ Robinson, Trevor (1959). "Alkaloids". Scientific American. 201 (1): 113–123. ISSN 0036-8733.
  8. ↑ 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.