Catharanthine

Names

[ Name ]:
Catharanthine

[Synonym ]:
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)-

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]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> nAChR

Signaling Pathways >> Neuronal Signaling >> nAChR

Natural Products >> Alkaloid

Research 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.

[Related Small Molecules]

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

MSDS

Click to get detail MSDS

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

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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 ...