methyl (5beta)-3,4-didehydroibogamine-18-carboxylate
Catharanthine
CAS: 2468-21-5
Molecular Formula: C21H24N2O2
methyl (5beta)-3,4-didehydroibogamine-18-carboxylate - Names and Identifiers
| Name | Catharanthine |
| Synonyms | 18-beta)-lph catharanthin Catharanthine (+)-CATHRANTHINE 4-Didehydrocoronaridine (+)-3,4-didehydrocoronaridine methyl (5beta)-3,4-didehydroibogamine-18-carboxylate methyl (5beta,18beta)-3,4-didehydroibogamine-18-carboxylate methyl (2alpha,5beta,18beta)-3,4-didehydroibogamine-18-carboxylate ibogamine-18-carboxylicacid,3,4-didehydro-,methylester,(2-alpha,5-beta,6-a methyl(2-alpha,5-beta,6-alpha,18-beta)-3,4-didehydroibogamine-18-carboxylate |
| CAS | 2468-21-5 |
| EINECS | 219-586-6 |
| InChI | InChI=1/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 |
methyl (5beta)-3,4-didehydroibogamine-18-carboxylate - Physico-chemical Properties
| Molecular Formula | C21H24N2O2 |
| Molar Mass | 336.43 |
| Density | 1.1367 (rough estimate) |
| Melting Point | 138-1400C |
| Boling Point | 472.9°C (rough estimate) |
| Specific Rotation(α) | D27 +29.8° (CHCl3) |
| Flash Point | 251.1°C |
| Solubility | DMSO : ≥ 100 mg/mL (297.24 mM);H2O : < 0.1 mg/mL (insoluble) |
| Vapor Presure | 8.33E-10mmHg at 25°C |
| Appearance | White powder |
| Color | white to beige |
| pKa | 6.8(at 25℃) |
| Storage Condition | Sealed in dry,Store in freezer, under -20°C |
| Refractive Index | 1.6500 (estimate) |
| MDL | MFCD01753356 |
| Physical and Chemical Properties | White crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from Catharanthus roseus. |
methyl (5beta)-3,4-didehydroibogamine-18-carboxylate - Risk and Safety
| WGK Germany | 3 |
methyl (5beta)-3,4-didehydroibogamine-18-carboxylate - Reference
| Reference Show more | 1. Li Yiwen, Gao Mingbo, Yu Xiaoqian, et al. Study on Callus Induction of Catharanthus roseus and Extraction of Vinblastine [J]. Guangzhou Chemical Industry, 2019, 047(016):99-101. 2. Bai Daoming, Zhou Guangtao, Dai Long. Optimization of Process for Purification of Catharanthus roseus Chinese Duoling and Vinblastine by Cation Exchange Resin [J]. Journal of Liaoning University of Traditional Chinese Medicine, 2012, 014(012):182-184. 3. [IF = 5.875] Fangyuan Wang et al."Facile nose-to-brain delivery of rotigotine-loaded polymer micelles thermosensitive hydrogels: In vitro characterization and in vivo behavior study." Int J Pharmaceut. 2020 Mar;577:119046 4. [IF = 5.118] Wenzhu Tang et al."Enhancement of Vindoline and Catharanthine Accumulation, Antioxidant Enzymes Activities, and Gene Expression Levels in Catharanthus roseus Leaves by Chitooligosaccharides Elicitation." Mar Drugs. 2022 Mar;20(3):188 |
methyl (5beta)-3,4-didehydroibogamine-18-carboxylate - Reference Information
| overview | vinblastine is one of the alkaloids in Catharanthus roseus. Animal experiments show that it has antihypertensive effect and is one of the important starting materials for the synthesis of anti-tumor drugs vinorelbine tartrate, vinblastine sulfate and vincristine, which are widely used in clinic, and have wide application value. |
| plant source | dried stems and leaves of Catharanthus roseus (L.) G. Don of Apocynaceae plant |
| pharmacological research | study the chemical constituents of Catharanus (Catharanthus roselts). Methods Repeated silica gel, Rp-18, Sephadex LH-20 and other column chromatography were used to separate and purify the volume fraction 95% ethanol extract of Catharanthus roseus, and the structure of the compound was identified according to physical and chemical constants and spectral data. Catharanthus roseus total ethanol extract and n-butanol extract showed strong inhibitory activity on liver cancer cells in vitro, while petroleum ether extract, ethyl acetate extract and water extract had no activity. It indicates that the n-butanol extract part is the cytotoxic active site of liver cancer in Catharanthus roseus in vitro. |
| application | vinblastine is one of the alkaloids in Catharanthus roseus. Animal experiments show that it has antihypertensive effect and is one of the important starting materials for the synthesis of anti-tumor drugs vinorelbine tartrate, vinblastine sulfate and vincristine, which are widely used in clinic. |
| chemical properties | white crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from periwinkle. |
| use | inhibit nicotinic receptor-mediated diaphragm contraction, IC50:59.6 μM. Catharanthine is a precursor of the anti-tumor drugs vinblastine and vincristine, formed by dimerization of catharanthine with vindoline. Catharanthine itself is an inhibitor of tubulin self-assembly into microtubules, although not so potent as vinblastine or vincristine. Catharanthine also has anticholinergic activity. It shows muscarinic antagonism at 10 microM and fully inhibited nicotinic receptor mediated diaphragm contractions with an IC50 of 59.6 microM. can inhibit spindle formation, ribonucleic acid and fat synthesis. Vinblastine sulfate can be used to treat Hodgkin's disease and villous glandular epithelial cancer. It has a good effect on lymphatic cancer, acute leukemia, breast cancer, ovarian cancer, testicular cancer, etc. |
| category | toxic substances |
| toxicity classification | low toxicity |
| acute toxicity | abdominal cavity-rat LD50: > 800 mg/kg |
| flammability hazard characteristics | thermal decomposition discharges toxic nitrogen oxide smoke |
| storage and transportation characteristics | warehouse low temperature ventilation and drying |
| fire extinguishing agent | water, carbon dioxide, foam, dry powder |
Last Update：2024-04-09 20:52:54
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