Catharanthine

Modify Date: 2024-01-02 17:06:55

Catharanthine Structure
Catharanthine structure
 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

 Use of Catharanthine


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].

 Names

Name catharanthine
Synonym More Synonyms

 Catharanthine Biological Activity

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
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

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
NH6732500
CHEMICAL NAME :
Ibogamine-18-carboxylic acid, 3,4-didehydro-, methyl ester, (2-alpha,5-beta,6-alpha,18-beta)-
CAS REGISTRY NUMBER :
2468-21-5
LAST UPDATED :
199512
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C21-H24-N2-O2

HEALTH HAZARD DATA

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)-
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