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Ricinine Sale

(Synonyms: 蓖麻鹼) 目录号 : GC49485

A piperidine alkaloid with diverse biological activities

Ricinine Chemical Structure

Cas No.:524-40-3

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Ricinine is a piperidine alkaloid that has been found in R. communis and has diverse biological activities.1,2,3,4 It is an inhibitor of acetylcholinesterase (AChE; IC50 = 54.5 µg/ml).2 It scavenges ABTS radicals and chelates iron (IC50s = 102.65 and 104.32 µg/ml, respectively). Ricinine is toxic to adult A. gambiae when used at a concentration of 0.04 mg/ml in a feeding assay.3 It is also toxic to mice with an intraperitoneal LD50 value of 340 mg/kg but an oral LD50 value of 3,000 mg/kg.1 It has been used as a biomarker of ricin poisoning.4

1.Franke, H., Scholl, R., and Aigner, A.Ricin and Ricinus communis in pharmacology and toxicology-from ancient use and "Papyrus Ebers" to modern perspectives and "poisonous plant of the year 2018"Naunyn Schmiedebergs Arch. Pharmacol.392(10)1181-1208(2019) 2.Khan, B.R., Ghous, T., Rasheed, A., et al.Evaluation of anti-acetylcholinesterase activity and antioxidant potential of ricinine (a central nervous system stimulant) isolated from Ricinius communis L.J. Chem. Soc. Pak.38(2)326-332(2016) 3.Wachira, S.W., Omar, S., Jacob, J.W., et al.Toxicity of six plant extracts and two pyridone alkaloids from Ricinus communis against the malaria vector Anopheles gambiaeParasit. Vectors7312(2014) 4.Johnson, R.C., Lemire, S.W., Woolfitt, A.R., et al.Quantification of ricinine in rat and human urine: A biomarker for ricin exposureJ. Anal. Toxicol.29(3)149-155(2005)

Chemical Properties

Cas No. 524-40-3 SDF Download SDF
别名 蓖麻鹼
Canonical SMILES N#CC1=C(C=CN(C)C1=O)OC
分子式 C8H8N2O2 分子量 164.2
溶解度 DMSO: slightly soluble,Methanol: slightly soluble 储存条件 Store at -20°C,protect from light
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1 mM 6.0901 mL 30.4507 mL 60.9013 mL
5 mM 1.218 mL 6.0901 mL 12.1803 mL
10 mM 0.609 mL 3.0451 mL 6.0901 mL
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Research Update

Microwave-Assisted Extraction of Ricinine from Ricinus communis Leaves

Antioxidants (Basel) 2019 Oct 1;8(10):438.PMID:31581463DOI:10.3390/antiox8100438.

The alkaloid Ricinine (3-cyano-4-methoxy-N-methyl-2-pyridone) is found in different parts of the Ricinus communis plant and is known to possess several bioactive properties, including strong antioxidant activity. In this study, a new microwave-assisted extraction (MAE) method was developed for the recovery of Ricinine from R. communis leaves. The extraction variables studied were extraction temperature (between 125 °C and 175 °C), microwave power (between 500 W and 1000 W), extraction time (between 5 min and 15 min), extraction solvent (between 10% and 90% of EtOAc in MeOH), and solvent-to-sample ratio (between 25:1 mL and 50:1 mL of solvent per gram of the sample). On studying the effects of extraction variables, both solvent and liquid-to-solid ratio were found to exhibit the highest effects on Ricinine recovery. A fast (15 min) microwave-assisted extraction method was developed (high temperatures can be applied because the stability of Ricinine is proven in the literature), allowing for the recovery of Ricinine from R. communis leaves. The study revealed that R. communis leaves had almost 1.5 mg g-1 (dried weight) of Ricinine.

Synthesis of new selective cytotoxic Ricinine analogues against oral squamous cell carcinoma

Nat Prod Res 2021 Jul;35(13):2145-2156.PMID:31526148DOI:10.1080/14786419.2019.1663513.

Sixteen new analogues were synthesized from Ricinine and tested alongside with seven known analogues for their cytotoxic activity against oral cancer (SAS cells) and normal epithelial cells (L132 cells). In contrast to 5-FU, the synthesized Ricinine analogues did not show toxicity to normal cells. However, some of them inhibited the proliferation of oral cancer cells at 25 µM as evident from the MTT assay results. Ricinine analogue (19) was shown to be the most active derivative (69.22% inhibition). Potential targets involved in the oral cancer inhibitory activity of compound 19 were investigated using in-silico studies and western blot analysis. PTP1B was predicted to be a target for Ricinine using reverse docking approach. This prediction was confirmed by western blot analysis that revealed the downregulation of PTP1B protein by compound 19. Moreover, it showed downregulation of COX-2 which is also extensively expressed in oral cancer.

Ricinine-elicited seizures. A novel chemical model of convulsive seizures

Pharmacol Biochem Behav 2000 Apr;65(4):577-83.PMID:10764909DOI:10.1016/s0091-3057(99)00250-6.

The present investigation introduces ricinine-elicited seizures as a novel chemical model of convulsive seizure. Ricinine, a neutral alkaloid obtained from the plant Ricinus communis, induces seizures when administered to mice at doses higher than 20 mg/kg. Animals presenting seizures showed a marked preconvulsive phase followed by short duration hind limb myoclonus, respiratory spasms, and death. The lethal nature of Ricinine seizures is also pointed out as a good model to study the events causing death in clonic seizures, particularly those related to respiratory spasms, which are also observed in some types of human epilepsy. The behavioral signs of ricinine-elicited seizures are accompanied by electrographic alterations more evident during the preconvulsive phase in the cerebral cortex and more intense during the ictal phase both in the cortex and in the hippocampus. The ricinine-elicited seizures may be inhibited by diazepam but not by phenobarbital, phenytoin, or ethosuximide. Micromolar concentrations of Ricinine cause a small decrease in the binding of [3H]-flunitrazepam to cerebral cortex membranes, but do not alter the binding of other radioligands to AMPA, 5-HT(1A), muscarinic, and alpha(1)-adrenergic receptors. Although Ricinine presents a cyanide radical, only higher doses of Ricinine (4 mM) caused a small impairment of mitochondrial respiration. These results suggest that the mechanism of action of Ricinine probably involves the benzodiazepine site in the GABA(A) receptor. This may represent a new mechanism of drug-elicited seizures that may contribute to a better understanding of epilepsy and to new therapeutic approaches to this disease.

Serial Ricinine levels in serum and urine after ricin intoxication

J Anal Toxicol 2013 Jun;37(5):313-7.PMID:23592744DOI:10.1093/jat/bkt026.

Ricinine is an alkaloid present in the castor bean plant (Ricinus communis) that can be used as a biomarker for ricin poisoning. Serial Ricinine levels are reported in the serum and urine of a patient suffering from intentional ricin intoxication. The patient was brought to the hospital 4 h after injection and oral intake of a castor bean extract, but died 38 h later, despite intensive medical care. Ricinine was isolated from the samples by solid-phase extraction and quantitatively determined by isotopic dilution liquid chromatography-mass spectrometry. The Ricinine level in serum declined from 33 to 23 ng/mL between 10 and 29 h post-exposure. Three urine samples collected from 12 to 41 h after ricin intoxication showed Ricinine concentrations in the range of 20-58 ng/mL. The creatinine corrected values (21-30 µg/g) indicated a concentration-time profile with a maximum Ricinine level in urine between 12 and 29 h after exposure.

Human plasma Ricinine quantification by LC-HRMS after micro-solid-phase elution

Biomed Chromatogr 2023 May;37(5):e5604.PMID:36776032DOI:10.1002/bmc.5604.

A rapid, sensitive and specific method for Ricinine identification and quantification in plasma has been developed by LC-HRMS. Deuterated Ricinine was used as the internal standard. From 100 μL of plasma, Ricinine was extracted using micro-solid-phase elution, which allows a reduced extraction time, by eliminating the evaporation step. Eluate is directly injected into the LC-HRMS system. Chromatographic separation was performed using a reverse-phase C18 column with a 4.5 min gradient elution. The method was validated according to European Medicines Agency guidelines. Linearity was verified between 0.25 and 500.0 ng/mL; the maximum precision calculated was 19.9% for the lower limit of quantitation and 9.6% for quality control, and accuracy was within ± 5.6% of the nominal concentrations. Selectivity, carryover, matrix effect and stability were also verified according to European Medicines Agency guidelines. The method allows the rapid and reliable identification of ricin-exposed victims in case of terrorist attacks or poisonings: three intoxication cases are reported.