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 1430
Casein kinase I alpha 6 Target ID: CHEMBL2793 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25124862	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 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
Forensic determination of ricin and the alkaloid marker ricinine from castor bean extracts.	2001 Sep	11569541
Amino acid and monoamine alterations in the cerebral cortex and hippocampus of mice submitted to ricinine-induced seizures.	2002 Jul	12062566
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 Nov 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 Sep	15382509
Quantification of ricinine in rat and human urine: a biomarker for ricin exposure.	2005 Apr	15842756
Fatal ricin toxicosis in a puppy confirmed by liquid chromatography/mass spectrometry when using ricinine as a marker.	2007 Mar	17402623
A simple method for screening and quantification of ricinine in feed with HPLC and LC-MS.	2009 Aug	19772732
Suicidal death after injection of a castor bean extract (Ricinus communis L.).	2009 Aug 10	19477090
Multisystem organ failure after large volume injection of castor oil.	2009 Jan	19131711
Quantification of L-abrine in human and rat urine: a biomarker for the toxin abrin.	2009 Mar	19239732
High-speed counter-current chromatographic isolation of ricinine, an insecticide from Ricinus communis.	2009 May 8	19249053
Ricin toxicokinetics and its sensitive detection in mouse sera or feces using immuno-PCR.	2010 Sep 22	20877567

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

RICININE

Common Name

English

RICININE [MI]

Common Name

English

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

Systematic Name

English

NSC-409913

Code

English

NSC-642604

Code

English

Code System Code Type Description

WIKIPEDIA

Ricinine