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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 of RICININE

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

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

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.