CAS 2468-21-5|Catharanthine
| Common Name | Catharanthine | ||
|---|---|---|---|
| CAS Number | 2468-21-5 | Molecular Weight | 336.427 |
| Density | 1.3±0.1 g/cm3 | Boiling Point | 491.5±45.0 °C at 760 mmHg |
| Molecular Formula | C21H24N2O2 | Melting Point | 138-140ºC |
| MSDS | USA | Flash Point | 251.1±28.7 °C |
Names
| Name | catharanthine |
|---|---|
| Synonym | More Synonyms |
Catharanthine BiologicalActivity
| Description | Catharanthine inhibits nicotinic receptor mediated diaphragm contractions with IC50 of 59.6 μM.Target: nAChRCatharanthine 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 [1]. 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 [2]. 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 [3]. 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 [4]. |
|---|---|
| Related Catalog | Signaling Pathways >>Membrane Transporter/Ion Channel >>nAChRSignaling Pathways >>Neuronal Signaling >>nAChRNatural Products >>AlkaloidResearch Areas >>Neurological Disease |
| References | [1]. Pereira, D.M., et al., Pharmacological effects of Catharanthus roseus root alkaloids in acetylcholinesterase inhibition and cholinergic neurotransmission. Phytomedicine, 2010. 17(8-9): p. 646-52. [2]. Prakash, V. and S.N. Timasheff, Mechanism of interaction of vinca alkaloids with tubulin: catharanthine and vindoline. Biochemistry, 1991. 30(3): p. 873-80. [3]. Williams, J.A., Catharanthine: a novel stimulator of pancreatic enzyme release. Cell Tissue Res, 1978. 192(2): p. 277-84. [4]. Arias, H.R., et al., Catharanthine alkaloids are noncompetitive antagonists of muscle-type nicotinic acetylcholine receptors. Neurochem Int, 2010. 57(2): p. 153-61. |
Chemical & Physical Properties
| Density | 1.3±0.1 g/cm3 |
|---|---|
| Boiling Point | 491.5±45.0 °C at 760 mmHg |
| Melting Point | 138-140ºC |
| Molecular Formula | C21H24N2O2 |
| Molecular Weight | 336.427 |
| Flash Point | 251.1±28.7 °C |
| Exact Mass | 336.183777 |
| PSA | 45.33000 |
| LogP | 4.05 |
| Vapour Pressure | 0.0±1.2 mmHg at 25°C |
| Index of Refraction | 1.663 |
| InChIKey | CMKFQVZJOWHHDV-NQZBTDCJSA-N |
| SMILES | CCC1=CC2CN3CCc4c([nH]c5ccccc45)C(C(=O)OC)(C2)C13 |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- >800 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- BCPCA6 Biochemical Pharmacology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1958- Volume(issue)/page/year: 26,1213,1977
Safety Information
| Hazard Codes | Xn |
|---|---|
| RIDADR | NONH for all modes of transport |
Articles25
More Articles| Catharanthine dilates small mesenteric arteries and decreases heart rate and cardiac contractility by inhibition of voltage-operated calcium channels on vascular smooth muscle cells and cardiomyocytes. J. Pharmacol. Exp. Ther. 345(3) , 383-92, (2013) Catharanthine is a constituent of anticancer vinca alkaloids. Its cardiovascular effects have not been investigated. This study compares the in vivo hemodynamic as well as in vitro effects of catharan... | |
| The leaf epidermome of Catharanthus roseus reveals its biochemical specialization. Plant Cell 20(3) , 524-42, (2008) Catharanthus roseus is the sole commercial source of the monoterpenoid indole alkaloids (MIAs), vindoline and catharanthine, components of the commercially important anticancer dimers, vinblastine and... | |
| Simultaneous determination of vinblastine and its monomeric precursors vindoline and catharanthine in Catharanthus roseus by capillary electrophoresis-mass spectrometry. J. Sep. Sci. 34 , 2885-2892, (2011) Catharanthus roseus is an important dicotyledonous medicinal plant that contains various anticancer components, such as vinblastine (VLB) and its monomeric precursors (vindoline and catharanthine). A ... |
Synonyms
| Ibogamine-18-carboxylic acid, 3,4-didehydro-, methyl ester, (2α,5β,18β)- |
| Methyl (2α,5β,18β)-3,4-didehydroibogamine-18-carboxylate |
| Catharanthine Sulphate |
| catharintine |
| CatharanthineSulfateBase |
| catharantine |
| (2α,5β,6α,18β)-3,4-Didehydroibogamine-18-carboxylic acid methyl ester |
| Ibogamine-18-carboxylic acid, 3,4-didehydro-, methyl ester, (2a,5b,6a,18b)- |
| (+)-3,4-Didehydrocoronaridine |
| Catharanthine |
| catharanthin |
| UNII-WT0YJV846J |
| catharinthine |
| MFCD01753356 |
| Ibogamine-18-carboxylic acid, 3,4-didehydro-, methyl ester, (2α,5β,6α,18β)- |
