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MedKoo Cat#: 412445 | Name: Catharanthine hydrochloride

Description:

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

Catharanthine hydrochloride is the salt from of Catharanthine (free base), 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 hydrochloride
Catharanthine hydrochloride
CAS#2645-61-6 (HCl)

Theoretical Analysis

MedKoo Cat#: 412445

Name: Catharanthine hydrochloride

CAS#: 2645-61-6 (HCl)

Chemical Formula: C21H25ClN2O2

Exact Mass: 372.1605

Molecular Weight: 372.89

Elemental Analysis: C, 67.64; H, 6.76; Cl, 9.51; N, 7.51; O, 8.58

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
2468-21-5 (free base) 2645-61-6 (HCl)
Synonym
Catharanthine hydrochloride; Catharanthine HCl; EINECS 220-159-1
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 hydrochloride
InChi Key
AVBOKMGDTOZFMW-GYMDHWDQSA-N
InChi Code
InChI=1S/C21H24N2O2.ClH/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;1H/t13-,19+,21-;/m0./s1
SMILES Code
O=C([C@]1(C2)[C@](C(CC)=C[C@]2([H])C3)([H])N3CCC4=C1NC5=C4C=CC=C5)OC.[H]Cl
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

Preparing Stock Solutions

The following data is based on the product molecular weight 372.89 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
1: 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. 2: 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. 3: 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. 4: 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. 5: 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. 6: Lin C, Cai J, Yang X, Hu L, Lin G. Liquid chromatography mass spectrometry simultaneous determination of vindoline and catharanthine in rat plasma and its application to a pharmacokinetic study. Biomed Chromatogr. 2015 Jan;29(1):97-102. doi: 10.1002/bmc.3244. Epub 2014 May 15. PMID: 24828449. 7: Zhou ML, Hou HL, Zhu XM, Shao JR, Wu YM, Tang YX. Soybean transcription factor GmMYBZ2 represses catharanthine biosynthesis in hairy roots of Catharanthus roseus. Appl Microbiol Biotechnol. 2011 Aug;91(4):1095-105. doi: 10.1007/s00253-011-3288-1. Epub 2011 May 17. PMID: 21590290. 8: Caputi L, Franke J, Farrow SC, Chung K, Payne RME, Nguyen TD, Dang TT, Soares Teto Carqueijeiro I, Koudounas K, Dugé de Bernonville T, Ameyaw B, Jones DM, Vieira IJC, Courdavault V, O'Connor SE. Missing enzymes in the biosynthesis of the anticancer drug vinblastine in Madagascar periwinkle. Science. 2018 Jun 15;360(6394):1235-1239. doi: 10.1126/science.aat4100. Epub 2018 May 3. PMID: 29724909. 9: 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. 10: Benyammi R, Paris C, Khelifi-Slaoui M, Zaoui D, Belabbassi O, Bakiri N, Meriem Aci M, Harfi B, Malik S, Makhzoum A, Desobry S, Khelifi L. Screening and kinetic studies of catharanthine and ajmalicine accumulation and their correlation with growth biomass in Catharanthus roseus hairy roots. Pharm Biol. 2016 Oct;54(10):2033-43. doi: 10.3109/13880209.2016.1140213. Epub 2016 Mar 17. PMID: 26983347.