RICININE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H8N2O2
Molecular Weight	164.1613
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(C#N)C(=O)N(C)C=C1

InChI

InChIKey=PETSAYFQSGAEQY-UHFFFAOYSA-N

InChI=1S/C8H8N2O2/c1-10-4-3-7(12-2)6(5-9)8(10)11/h3-4H,1-2H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22069699 | https://www.ncbi.nlm.nih.gov/pubmed/29334239 | https://www.ncbi.nlm.nih.gov/pubmed/25124862 | https://www.ncbi.nlm.nih.gov/pubmed/10764909

Ricinine is an alkaloid originally isolated from the Ricinus communis, or castor-oil plant. Ricinine can be found in all parts of the plant and it is a quite strong insecticide. The castor seeds contain approximately 0.2% of the alkaloid. Ricinine or 3-cyano-4-methoxy-N-methyl-2-pyridone (CAS 524-40-3) belongs to the group of piperidine alkaloids. Ricinine is a useful scaffold for the synthesis of new antimicrobial and antiquorum-sensing derivatives in spite of its poor contribution to the antimicrobial activity of the plant extracts. Ricinine activated the Wnt signaling pathway by inhibiting casein kinase 1α. Ricinine-elicited seizures as a novel chemical model of convulsive seizure.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Wnt signaling pathway 13 Target ID: GO:0016055 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25124862	Activator 1447
Casein kinase I alpha 6 Target ID: CHEMBL2793 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25124862	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619 Sources: https://patents.google.com/patent/CN101129365A	Primary		Preclinical	Unknown Approved Use Unknown
Amnesia 11 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10418776/	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Ricin toxicokinetics and its sensitive detection in mouse sera or feces using immuno-PCR.	2010-09-22	20877567
Suicidal death after injection of a castor bean extract (Ricinus communis L.).	2009-08-10	19477090
A simple method for screening and quantification of ricinine in feed with HPLC and LC-MS.	2009-08	19772732
High-speed counter-current chromatographic isolation of ricinine, an insecticide from Ricinus communis.	2009-05-08	19249053
Quantification of L-abrine in human and rat urine: a biomarker for the toxin abrin.	2009-03	19239732
Multisystem organ failure after large volume injection of castor oil.	2009-01	19131711
Fatal ricin toxicosis in a puppy confirmed by liquid chromatography/mass spectrometry when using ricinine as a marker.	2007-03	17402623
Quantification of ricinine in rat and human urine: a biomarker for ricin exposure.	2005-04	15842756
Reliable identification and quantification of trichothecenes and other mycotoxins by electron impact and chemical ionization-gas chromatography-mass spectrometry, using an ion-trap system in the multiple mass spectrometry mode. Candidate reference method for complex matrices.	2004-11-12	15595550
Activity of Ricinus communis (Euphorbiaceae) and ricinine against the leaf-cutting ant Atta sexdens rubropilosa (Hymenoptera: Formicidae) and the symbiotic fungus Leucoagaricus gongylophorus.	2004-09	15382509
Amino acid and monoamine alterations in the cerebral cortex and hippocampus of mice submitted to ricinine-induced seizures.	2002-07	12062566
Forensic determination of ricin and the alkaloid marker ricinine from castor bean extracts.	2001-09	11569541

Patents

Sample Use Guides

In Vivo Use Guide

mice: 60 mg/kg body weight, orally, reduced the extensor tonus phase of convulsion by MES-induced seizures in albino mice. However, ricinine induces seizures when administered to mice at doses higher than 20 mg/kg. In experimental mouse models ricinine causes hyperactivity, seizure and subsequent death due to respiratory arrest. LD50 values for ricinine were 340 mg/kg for intraperitoneal and 3 g/kg for oral incorporation.

Route of Administration: Oral

In Vitro Use Guide

higher doses of ricinine (4 mM) caused a small impairment of mitochondrial respiration.

Name

Type

Language

NSC-409913

Preferred Name

English

RICININE

Common Name

English

RICININE [MI]

Common Name

English

1,2-DIHYDRO-4-METHOXY-1-METHYL-2-OXONICOTINONITRILE

Systematic Name

English

NSC-642604

Code

English

Code System Code Type Description

WIKIPEDIA

Ricinine