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MedKoo Cat#: 412444 | Name: Catharanthine free base
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Catharanthine free base is a terpene indole alkaloid produced by the medicinal plant Catharanthus roseus and Tabernaemontana_divaricata. Catharanthine is derived from strictosidine, but the exact mechanism by which this happens is currently unknown. Catharanthine is an indole moiety of dimeric vinca alkaloids vinblastine & vincristine.

Chemical Structure

Catharanthine free base
Catharanthine free base
CAS#2468-21-5 (free base)

Theoretical Analysis

MedKoo Cat#: 412444

Name: Catharanthine free base

CAS#: 2468-21-5 (free base)

Chemical Formula: C21H24N2O2

Exact Mass: 336.1838

Molecular Weight: 336.43

Elemental Analysis: C, 74.97; H, 7.19; N, 8.33; O, 9.51

Price and Availability

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25mg USD 350.00 2 Weeks
100mg USD 650.00 2 Weeks
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Related CAS #
2468-21-5 (free base) 2645-61-6 (HCl)
Synonym
Catharanthine; Catharanthin; Catharanthine Base; (+)-3,4-Didehydrocoronaridine
IUPAC/Chemical Name
methyl (6R,6aR,9R)-7-ethyl-9,10,12,13-tetrahydro-5H-6,9-methanopyrido[1',2':1,2]azepino[4,5-b]indole-6(6aH)-carboxylate
InChi Key
CMKFQVZJOWHHDV-NQZBTDCJSA-N
InChi Code
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
SMILES Code
CCC1=C[C@@H]2CN3CCc(c([C@@]([C@@H]13)(C(OC)=O)C2)[nH]4)c5c4cccc5
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Catharanthine inhibits nicotinic receptor mediated diaphragm contractions with IC50 of 59.6 μM.
In vitro activity:
Catharanthine inhibited Ba2+ currents (P < 0.01) through VOCCs measured in isolated single VSMCs of the MA (Fig. 10, A and B). Specifically, the Ba2+ current density at 0 mV (–3.0 ± 0.3 pA/pF) was reduced (P < 0.01; n = 8 cells) to −1.62 ± 0.3 pA/pF at 3 µM, −0.93 ± 0.2 pA/pF at 10 µM, and −0.26 ± 0.1 pA/pF at 30 µM catharanthine. These data support the conclusion that the BP-lowering and vasodilatory effects of catharanthine occur as a result of inhibition of VOCCs in VSMCs of the MA. Catharanthine also dose-dependently inhibited (P < 0.05) VOCCs in cardiomyocytes (Fig. 11, A and B). Specifically, Ca2+ currents through cardiomyocytes at 0 mV were reduced from −4.0 ± 0.5 pA/pF to −2.3 ± 0.5 pA/pF at 100 µM, −1.3 ± 0.3 pA/pF at 300 µM, and −0.45 ± 0.2 pA/pF at 1 mM catharanthine. The inhibitory effect of catharanthine on VOCC currents was less potent (P < 0.01) in cardiomyocytes (IC50 = 224 ± 80 µM; Fig. 11C) than in VSMCs from MA (IC50 = 8.4 ± 2.5 µM; Fig. 10C). Reference: J Pharmacol Exp Ther. 2013 Jun;345(3):383-92. https://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=23532933
In vivo activity:
Intravenous administration of vehicle did not affect the basal BP or HR for a period of 1 hour (Fig. 1). In contrast, administration of catharanthine (0.5–20 mg/kg i.v.) evoked dose-dependent reductions in both BP and HR. The data from a representative tracing are shown in Fig. 2, A and B. At low doses (0.5–5 mg/kg), catharanthine evoked rapid, transient reductions in BP and HR (lasting <2 minutes), whereas at higher doses (10 and 20 mg/kg), the BP and HR reductions were sustained. The maximal reductions in BP and HR were reached after about 10–30 seconds postinjection, respectively. The responses at all concentrations reached stable levels after 5 minutes. The data from several experiments confirmed that BP decreased (P < 0.01) by more than 50% from 101 ± 12 mmHg (control value) to 48 ± 7 mm Hg after the administration of the highest dose (20 mg/kg) of catharanthine (Fig. 2C). Similarly, HR decreased (P < 0.05) from 399 ± 12 beats/min in control conditions to 297 ± 14 beats/min after the administration of 20 mg/kg catharanthine (Fig. 2D). It is clear that catharanthine causes sustained dose-dependent reductions in both BP and HR. To further explore the action of catharanthine on the heart, we measured intraventricular pressure-volume relationships using an impedance catheter. The representative data from a single experiment for the fall in LVSBP and the dP/dtmax attained after a single dose of catharanthine (10 mg/kg) administration are shown in Fig. 3A. Consistent with the BP results, peak LVSBPs were reduced after administration of increasing doses (1, 3, 10 mg/kg dose i.v.) of catharanthine in a concentration-dependent manner by values of 10 ± 1 mm Hg, 17 ± 2 mm Hg, and 23 ± 1 mm Hg at nadir (approximately 30 seconds postinjection), and by 5 ± 1 mm Hg, 8 ± 2 mm Hg, and 9 ± 1 mm Hg at steady state (approximately 5 minutes postinjection), respectively (Fig. 3B). Catharanthine dose-dependently decreased the maximal time derivative of the left ventricular pressure (i.e., dP/dtmax) with a pronounced transient effect 30 seconds after catharanthine administration, which reached a stable level approximately 5 minutes postinjection (Fig. 3, A and C). In addition to decreasing dP/dtmax, catharanthine also dose-dependently decreased the slope of the ESPVR from 0.18 ± 0.01 mm Hg/µl in the absence of drug to 0.06 ± 0.01 mm Hg/µl (measured approximately 5 min postinjection of 10 mg/kg catharanthine), further demonstrating that catharanthine impairs cardiac contractility (Fig. 4). Reference: J Pharmacol Exp Ther. 2013 Jun;345(3):383-92. https://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=23532933
Solvent mg/mL mM
Solubility
DMSO 67.0 199.15
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 336.43 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
1. Jadhav A, Liang W, Papageorgiou PC, Shoker A, Kanthan SC, Balsevich J, Levy AS, Heximer S, Backx PH, Gopalakrishnan V. 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. doi: 10.1124/jpet.112.199661. Epub 2013 Mar 26. PMID: 23532933. 2. Xu M, Dong J, Zhu M. Effect of nitric oxide on catharanthine production and growth of Catharanthus roseus suspension cells. Biotechnol Bioeng. 2005 Feb 5;89(3):367-71. doi: 10.1002/bit.20334. PMID: 15744842.
In vivo protocol:
1. Jadhav A, Liang W, Papageorgiou PC, Shoker A, Kanthan SC, Balsevich J, Levy AS, Heximer S, Backx PH, Gopalakrishnan V. 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. doi: 10.1124/jpet.112.199661. Epub 2013 Mar 26. PMID: 23532933.
1: Zhang J, Hansen LG, Gudich O, Viehrig K, Lassen LMM, Schrübbers L, Adhikari KB, Rubaszka P, Carrasquer-Alvarez E, Chen L, D'Ambrosio V, Lehka B, Haidar AK, Nallapareddy S, Giannakou K, Laloux M, Arsovska D, Jørgensen MAK, Chan LJG, Kristensen M, Christensen HB, Sudarsan S, Stander EA, Baidoo E, Petzold CJ, Wulff T, O'Connor SE, Courdavault V, Jensen MK, Keasling JD. A microbial supply chain for production of the anti-cancer drug vinblastine. Nature. 2022 Sep;609(7926):341-347. doi: 10.1038/s41586-022-05157-3. Epub 2022 Aug 31. PMID: 36045295; PMCID: PMC9452304. 2: Arias HR, Borghese CM, Germann AL, Pierce SR, Bonardi A, Nocentini A, Gratteri P, Thodati TM, Lim NJ, Harris RA, Akk G. (+)-Catharanthine potentiates the GABAA receptor by binding to a transmembrane site at the β(+)/α(-) interface near the TM2-TM3 loop. Biochem Pharmacol. 2022 May;199:114993. doi: 10.1016/j.bcp.2022.114993. Epub 2022 Mar 15. PMID: 35304861; PMCID: PMC9178925. 3: Arias HR, De Deurwaerdère P, El-Kasaby A, Di Giovanni G, Eom S, Lee JH, Freissmuth M, Chagraoui A. (+)-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. doi: 10.1016/j.ejphar.2022.175454. Epub 2022 Dec 19. PMID: 36549498. 4: Dwivedi GR, Tyagi R, Sanchita, Tripathi S, Pati S, Srivastava SK, Darokar MP, Sharma A. Antibiotics potentiating potential of catharanthine against superbug Pseudomonas aeruginosa. J Biomol Struct Dyn. 2018 Dec;36(16):4270-4284. doi: 10.1080/07391102.2017.1413424. Epub 2018 Jan 2. PMID: 29210342. 5: Jadhav A, Liang W, Papageorgiou PC, Shoker A, Kanthan SC, Balsevich J, Levy AS, Heximer S, Backx PH, Gopalakrishnan V. 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. doi: 10.1124/jpet.112.199661. Epub 2013 Mar 26. PMID: 23532933. 6: Moisan L, Thuéry P, Nicolas M, Doris E, Rousseau B. Formal synthesis of (+)-catharanthine. Angew Chem Int Ed Engl. 2006 Aug 11;45(32):5334-6. doi: 10.1002/anie.200601307. PMID: 16847851. 7: Kono M, Harada S, Nozaki T, Hashimoto Y, Murata SI, Gröger H, Kuroda Y, Yamada KI, Takasu K, Hamada Y, Nemoto T. Asymmetric Formal Synthesis of (+)-Catharanthine via Desymmetrization of Isoquinuclidine. Org Lett. 2019 May 17;21(10):3750-3754. doi: 10.1021/acs.orglett.9b01198. Epub 2019 Apr 25. PMID: 31021094. 8: Büchi G, Kulsa P, Ogasawara K, Rosati RL. Syntheses of velbanamine and catharanthine. J Am Chem Soc. 1970 Feb 25;92(4):999-1005. doi: 10.1021/ja00707a043. PMID: 5451014. 9: Tang W, Liu X, He Y, Yang F. Enhancement of Vindoline and Catharanthine Accumulation, Antioxidant Enzymes Activities, and Gene Expression Levels in Catharanthus roseus Leaves by Chitooligosaccharides Elicitation. Mar Drugs. 2022 Mar 3;20(3):188. doi: 10.3390/md20030188. PMID: 35323487; PMCID: PMC8950274. 10: Tam A, Gotoh H, Robertson WM, Boger DL. Catharanthine C16 substituent effects on the biomimetic coupling with vindoline: preparation and evaluation of a key series of vinblastine analogues. Bioorg Med Chem Lett. 2010 Nov 15;20(22):6408-10. doi: 10.1016/j.bmcl.2010.09.091. Epub 2010 Sep 19. PMID: 20932748; PMCID: PMC2957881. 11: Ramani S, Jayabaskaran C. Enhanced catharanthine and vindoline production in suspension cultures of Catharanthus roseus by ultraviolet-B light. J Mol Signal. 2008 Apr 25;3:9. doi: 10.1186/1750-2187-3-9. PMID: 18439256; PMCID: PMC2386454. 12: Williams JA. Catharanthine: a novel stimulator of pancreatic enzyme release. Cell Tissue Res. 1978 Sep 5;192(2):277-84. doi: 10.1007/BF00220745. PMID: 699016. 13: Gabriel P, Almehmadi YA, Wong ZR, Dixon DJ. A General Iridium-Catalyzed Reductive Dienamine Synthesis Allows a Five-Step Synthesis of Catharanthine via the Elusive Dehydrosecodine. J Am Chem Soc. 2021 Jul 28;143(29):10828-10835. doi: 10.1021/jacs.1c04980. Epub 2021 Jul 13. PMID: 34254792; PMCID: PMC8397322. 14: Xu M, Dong J, Zhu M. Effect of nitric oxide on catharanthine production and growth of Catharanthus roseus suspension cells. Biotechnol Bioeng. 2005 Feb 5;89(3):367-71. doi: 10.1002/bit.20334. PMID: 15744842. 15: Boon BA, Boger DL. Triarylaminium Radical Cation Promoted Coupling of Catharanthine with Vindoline: Diastereospecific Synthesis of Anhydrovinblastine and Reaction Scope. J Am Chem Soc. 2019 Sep 11;141(36):14349-14355. doi: 10.1021/jacs.9b06968. Epub 2019 Sep 3. PMID: 31442047; PMCID: PMC6750708. 16: Gorman M, Neuss N, Cone NJ. Vinca alkaloids. XVII. Chemistry of catharanthine. J Am Chem Soc. 1965 Jan 5;87(1):93-9. doi: 10.1021/ja01079a017. PMID: 5826975. 17: Grzech D, Hong B, Caputi L, Sonawane PD, O'Connor SE. Engineering the Biosynthesis of Late-Stage Vinblastine Precursors Precondylocarpine Acetate, Catharanthine, Tabersonine in Nicotiana benthamiana. ACS Synth Biol. 2023 Jan 20;12(1):27-34. doi: 10.1021/acssynbio.2c00434. Epub 2022 Dec 14. PMID: 36516122; PMCID: PMC9872167. 18: Chen Q, Chen Z, Lu L, Jin H, Sun L, Yu Q, Xu H, Yang F, Fu M, Li S, Wang H, Xu M. Interaction between abscisic acid and nitric oxide in PB90-induced catharanthine biosynthesis of catharanthus roseus cell suspension cultures. Biotechnol Prog. 2013 Jul-Aug;29(4):994-1001. doi: 10.1002/btpr.1738. Epub 2013 May 2. PMID: 23554409. 19: Giovanelli E, Moisan L, Comesse S, Leroux S, Rousseau B, Hellier P, Nicolas M, Doris E. Synthesis of fluorinated catharanthine analogues and investigation of their biomimetic coupling with vindoline. Org Biomol Chem. 2013 Sep 21;11(35):5885-91. doi: 10.1039/c3ob41170b. PMID: 23903701. 20: Sertel S, Fu Y, Zu Y, Rebacz B, Konkimalla B, Plinkert PK, Krämer A, Gertsch J, Efferth T. Molecular docking and pharmacogenomics of vinca alkaloids and their monomeric precursors, vindoline and catharanthine. Biochem Pharmacol. 2011 Mar 15;81(6):723-35. doi: 10.1016/j.bcp.2010.12.026. Epub 2011 Jan 8. PMID: 21219884.