SML0259

Catharanthine

≥95% (HPLC)

• Synonym(s): (+)-3,4-Didehydrocoronaridine, (2α,5β,6α,18β)-3,4-Didehydroibogamine-18-carboxylic acid methyl ester, 7-Ethyl-9,10,12,13-tetrahydro-6,9-methano-5H-pyrido[1′,2′:1,2]azepino[4,5-b]indole-6(6aH)-carboxylic acid methyl ester
• Empirical Formula (Hill Notation): C₂₁H₂₄N₂O₂
• CAS Number: 2468-21-5
• Molecular Weight: 336.43
• NACRES: NA.77
• PubChem Substance ID: 329825267
• UNSPSC Code: 12352200
• MDL number: MFCD01753356
• Assay: ≥95% (HPLC)
• Form: powder

Properties

• assay: ≥95% (HPLC)
• form: powder
• optical activity: [α]/D +30 to +38° (c=0.5, CDCl3)
• color: white to beige
• solubility: DMSO: 5 mg/mL (clear solution; warmed)
• shipped in: wet ice
• storage temp.: −20°C
• SMILES string: CCC1=C[C@@H]2C[N@H]3CCc4c([nH]c5ccccc45)[C@@](C2)([C@@H]13)C(=O)OC
• 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
• InChI key: CMKFQVZJOWHHDV-NQZBTDCJSA-N

Description

Biochem/physiol Actions

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 showed muscarinic antagonism at 10 microM and fully inhibited nicotinic receptor mediated diaphragm contractions with an IC₅₀ of 59.6 microM.

Catharanthine is a precursor of the anti-tumor drugs vinblastine and vincristine..Catharanthine is an inhibitor of tubulin self-assembly into microtubules.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302
• pcodes: P301 + P312 + P330
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable