CAS Number2468-21-5
SynonymsMethyl (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; (+)-3,4-Didehydrocoronaridine; Catharanthine; catharanthin; UNII-WT0YJV846J; catharinthine; MFCD01753356
Molecular FormulaC21H24N2O2
Molecular Weight336.427
Purity98.00%
Density1.3±0.1 g/cm3
Boiling Point491.5±45.0 °C at 760 mmHg
Melting Point138-140ºC
Appearancewhite powder
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 2468-21-5 |
| Catalog No. | 2A-9028592 |
| Chinese Name | 长春质碱 |
| Synonyms | 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; (+)-3,4-Didehydrocoronaridine; Catharanthine; catharanthin; UNII-WT0YJV846J; catharinthine; MFCD01753356 |
| Molecular Formula | C21H24N2O2 |
| Molecular Weight | 336.427 |
| Purity | 98.00 |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 491.5±45.0 °C at 760 mmHg |
| Melting Point | 138-140ºC |
| Appearance | white powder |
| Storage Condition | Warehouse low temperature ventilation and drying |
| Application | Catharanthine is an alkaloid extracted from Catharanthus roseus, which can inhibit nicotinic receptor-mediated septal contraction with an IC50 of 59.6μM. |
| PubChem ID | 15940443 |
| SMILES | CCC1=CC2CN3CCc4c([nH]c5ccccc45)C(C(=O)OC)(C2)C13 |
| InChI | InChI=1S/C21H24N2O2.H2O4S/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;1-5(2,3)4/h4-7,10,13,19,22H,3,8-9,11-12H2,1-2H3;(H2,1,2,3,4) |
| InChI Key | CMKFQVZJOWHHDV-NQZBTDCJSA-N |
| Hazard Symbols | transportation |
| MSDS | msds/28592_1_2468_21_5.pdf |
| Bioactivity | 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. 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 |
| Use of | Properties Articles25 Name catharanthine Synonym More Synonyms Catharanthine Biological Activity 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. Chemical & Physical Properties Molecular Formula C21H24N2O2 Exact Mass 336.183777 PSA 45.33000 Index of Refraction 1.663 InChIKey CMKFQVZJOWHHDV-NQZBTDCJSA-N |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available See reverse side of invoice or packing slip. |
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