Catharanthine

SKU: orb1700155

Description

Catharanthine is a bioactive alkaloid that potently inhibits nicotinic acetylcholine receptor function, as demonstrated by its suppression of receptor-mediated diaphragm muscle contractions with an IC50 of 59.6 µM. This small molecule is a valuable research tool for studying cholinergic signaling and neuromuscular junction physiology in both in vitro and ex vivo experimental models.

Research Area

Metabolism Research, Neuroscience, Pharmacology & Drug Discovery

Key Properties

• CAS Number: 2468-21-5
• MW: 336.43
• Purity: 99.55% (May vary between batches)
• Formula: C₂₁H₂₄N₂O₂
• SMILES: C(OC)(=O)[C@@]12[C@@]3([N@@](CC(C1)(C=C3CC)[H])CCC4=C2NC=5C4=CC=CC5)[H]
• Target: Calcium Channel,AChR
• Solubility: H2O:< 1 mg/mL (insoluble or slightly soluble);Ethanol:1 mg/mL (2.97 mM);10% DMSO+40% PEG300+5% Tween 80+45% Saline:3.3 mg/mL (9.81 mM);DMSO:40 mg/mL (118.9 mM)

Bioactivity

• Target IC50:
  nAChR:59.6 μM
• In Vitro:
  Catharanthine evokes a concentration-dependent attenuation of carbachol responses in the rat ileum preparation, producing rightward curve displacements and decreases in maximal agonist responses. The mixture of serpentine, plus ajmalicine and catharanthine reveals a concentration-dependent inhibitory effect of acethylcholinesterase (AchE), with an IC50 at ca. 2.25 μg/mL. Catharanthine can induce the self-association of tubulin into linear indefinite polymers with an efficacy that is 75% that of vinblastine or vincristine. Catharanthine binds to tubulin alpha-beta dimer with binding constant of 2.8 mM. Catharanthine stimulates release of amylase from pancreatic fragments and to cause extensive degranulation of pancreatic acinar cells with accumulation of membrane material in the Golgi region. Catharanthine induces a delayed release of Ca2+ from prelabeled pancreatic fragments as compared to bethanechol. Catharanthine inhibits epibatidine-induced Ca(2+) influx in TE671-α, -β, -γ, -δ cells in a noncompetitive manner with similar potencies IC50 of 17 mM-25 mM. Catharanthine inhibits [3H]TCP binding to the desensitized Torpedo AChR with higher affinity compared to the resting AChR. Catharanthine enhances [3H]cytisine binding to resting but activatable Torpedo AChRs, suggesting desensitizing properties.
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Storage & Handling

• Storage: -20°C
• Expiration Date: 12 months from date of receipt.
• Disclaimer: For research use only

Alternative Names

CalciumChannel, Ca channels, Ca2+ channels, Calcium Channel, Catharanthine, 3,4-Didehydrocoronaridine, 3, 4-Didehydrocoronaridine, (+)-3, 4-Didehydrocoronaridine, (+)-3,4-Didehydrocoronaridine, Inhibitor, inhibit, nAChR

Compound Identifiers

PubChem CID

5315744