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Catharanthine

CAT: 0804-HY-N0252-02Size: 10 mM - 1 mLDry Ice: NoHazardous: No
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CAT#:0804-HY-N0252-02Size:10 mM - 1 mL
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Catharanthine ((+) -3,4-Didehydrocoronaridine), a constituent of anticancer vinca alkaloids, inhibits voltage-operated L-type Ca2+ channel (VOCC) . Catharanthine has IC50s of 220 μM and 8 μM for VOCC currents in cardiomyocytes and vascular smooth muscle cells (VSMCs), respectively. Catharanthine lowers blood pressure (BP), heart rate (HR) . Catharanthine has anti-cancer activity[1][2].
CAS Number
2468-21-5
Product Name Alternative
(+) -3,4-Didehydrocoronaridine
UNSPSC
12352005
Hazard Statement
H302
Target
Calcium Channel
Type
Natural Products
Related Pathways
Membrane Transporter/Ion Channel; Neuronal Signaling
Applications
Cancer-programmed cell death
Field of Research
Cancer; Neurological Disease; Cardiovascular Disease
Assay Protocol
https://www.medchemexpress.com/catharanthine.html
Concentration
10mM
Purity
99.65
Solubility
DMSO : ≥ 100 mg/mL|H2O : < 0.1 mg/mL (ultrasonic)
Smiles
O=C([C@@]12C3=C(CC[N@](C4)[C@]1([H])C(CC)=C[C@@]4([H])C2)C5=CC=CC=C5N3)OC
Molecular Formula
C21H24N2O2
Molecular Weight
336.43
Precautions
H302
References & Citations
[1]Jadhav A, et al. 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. 2013 Jun;345 (3) :383-92.|[2]Hugo R Arias, et al. (+) -Catharanthine and (-) -18-methoxycoronaridine induce antidepressant-like activity in mice by differently recruiting serotonergic and norepinephrinergic neurotransmission. Eur J Pharmacol. 2023 Jan 15:939:175454.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
L-type calcium channel
Citation 01
Ind Crops Prod. 2025 Aug.|Cell Signal. 2025 Mar 29:111779.

Chemical Information

(+)-Catharanthine

Catharanthine is an organic heteropentacyclic compound and monoterpenoid indole alkaloid produced by the medicinal plant Catharanthus roseus via strictosidine. It is a methyl ester, a bridged compound, an organic heteropentacyclic compound, an alkaloid ester, a tertiary amino compound and a monoterpenoid indole alkaloid. It is a conjugate base of a catharanthine(1+).

CAS Number2468-21-5
PubChem CID5458190
IUPAC Namemethyl (1R,15R,18R)-17-ethyl-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate
Molecular FormulaC21H24N2O2
Molecular Weight336.4
XLogP2.8
Topological Polar Surface Area45.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Heavy Atom Count25
Formal Charge0
Complexity603
SMILES
CCC1=C[C@H]2C[C@]3([C@@H]1N(C2)CCC4=C3NC5=CC=CC=C45)C(=O)OC
InChI
InChI=1S/C21H24N2O2/c1-3-14-10-13-11-21(20(24)25-2)18-16(8-9-23(12-13)19(14)21)15-6-4-5-7-17(15)22-18/h4-7,10,13,19,22H,3,8-9,11-12H2,1-2H3/t13-,19+,21-/m0/s1
InChIKey
CMKFQVZJOWHHDV-NQZBTDCJSA-N
Chemical Structure
2D Structure
2D structure of (+)-Catharanthine
CAS: 2468-21-5
CID: 5458190
Formula: C21H24N2O2
MW: 336.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight336.4
XLogP32.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Exact Mass336.183778013
Monoisotopic Mass336.183778013
Topological Polar Surface Area45.3 Ų
Heavy Atom Count25
Formal Charge0
Complexity603
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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