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
CAS Number	524-40-3;
3D model (JSmol)	Interactive image;
3DMet	B00311;
ChEBI	CHEBI:18043;
ChEMBL	ChEMBL1329957;
ChemSpider	10216;
ECHA InfoCard	100.007.601
EC Number	208-359-7;
KEGG	C01526;
PubChem CID	10666;
UNII	130UFS7AE0;
CompTox Dashboard (EPA)	DTXSID50200412 ;
	InChI InChI=1S/C8H8N2O2/c1-10-4-3-7(12-2)6(5-9)8(10)11/h3-4H,1-2H3 Key: PETSAYFQSGAEQY-UHFFFAOYSA-N;
	SMILES Cn1ccc(c(c1=O)C#N)OC;
Properties
Chemical formula	C8H8N2O2
Molar mass	164.164 g·mol−1
Melting point	200 °C (392 °F; 473 K)
Hazards
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	340 mg/kg
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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]

References

^ 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.
^ 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.
^ 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.
^ 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.
^ ^a ^b ^c Henry, Thomas Anderson (1949). "Ricinine". The Plant Alkaloids (4th ed.). The Blakiston Company. p. 5.
^ 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.
^ 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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[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.

[henry-5] 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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Ricinine

See also

References