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MedKoo Cat#: 412812 | Name: Chelerythrine

Description:

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

Chelerythrine is a benzophenanthridine alkaloid present in the plant Chelidonium majus. It is a potent, selective, and cell-permeable protein kinase C inhibitor in vitro. And an efficacious antagonist of G-protein-coupled CB1 receptors.

Chemical Structure

Chelerythrine
Chelerythrine
CAS#34316-15-9 (cation)

Theoretical Analysis

MedKoo Cat#: 412812

Name: Chelerythrine

CAS#: 34316-15-9 (cation)

Chemical Formula: C21H18NO4+

Exact Mass: 348.1230

Molecular Weight: 348.38

Elemental Analysis: C, 72.40; H, 5.21; N, 4.02; O, 18.37

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 #
478-03-5 (hydroxide) 3895-92-9 (chloride) 34316-15-9 (cation)
Synonym
chelerythrine; Toddalin; Cheleritrine; Toddaline
IUPAC/Chemical Name
1,2-Dimethoxy-12-methyl(1,3)benzodioxolo(5,6-c)phenanthridinium
InChi Key
LLEJIEBFSOEYIV-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H18NO4/c1-22-10-16-13(6-7-17(23-2)21(16)24-3)14-5-4-12-8-18-19(26-11-25-18)9-15(12)20(14)22/h4-10H,11H2,1-3H3/q+1
SMILES Code
C[N+]1=CC2=C(OC)C(OC)=CC=C2C(C=CC3=C4)=C1C3=CC5=C4OCO5
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
>2 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 348.38 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: Saavedra A, Fernández-García S, Cases S, Puigdellívol M, Alcalá-Vida R, Martín-Flores N, Alberch J, Ginés S, Malagelada C, Pérez-Navarro E. Chelerythrine promotes Ca2+-dependent calpain activation in neuronal cells in a PKC-independent manner. Biochim Biophys Acta Gen Subj. 2017 Apr;1861(4):922-935. doi: 10.1016/j.bbagen.2017.01.021. Epub 2017 Jan 24. PMID: 28130160. 2: Jana J, Mondal S, Bhattacharjee P, Sengupta P, Roychowdhury T, Saha P, Kundu P, Chatterjee S. Chelerythrine down regulates expression of VEGFA, BCL2 and KRAS by arresting G-Quadruplex structures at their promoter regions. Sci Rep. 2017 Jan 19;7:40706. doi: 10.1038/srep40706. PMID: 28102286; PMCID: PMC5244364. 3: He N, Wang P, Wang P, Ma C, Kang W. Antibacterial mechanism of chelerythrine isolated from root of Toddalia asiatica (Linn) Lam. BMC Complement Altern Med. 2018 Sep 26;18(1):261. doi: 10.1186/s12906-018-2317-3. PMID: 30257662; PMCID: PMC6158911. 4: Zhang Q, Tian Y, Duan J, Wu J, Yan S, Chen H, Meng X, Owusu-Ansah KG, Zheng S. Chelerythrine ameliorates acute cardiac allograft rejection in mice. Transpl Immunol. 2016 Sep;38:78-83. doi: 10.1016/j.trim.2016.07.003. Epub 2016 Jul 19. PMID: 27450116. 5: Zhu Y, Pan Y, Zhang G, Wu Y, Zhong W, Chu C, Qian Y, Zhu G. Chelerythrine Inhibits Human Hepatocellular Carcinoma Metastasis in Vitro. Biol Pharm Bull. 2018 Jan 1;41(1):36-46. doi: 10.1248/bpb.b17-00451. Epub 2017 Oct 31. PMID: 29093327. 6: Heng WS, Cheah SC. Chelerythrine Chloride Downregulates β-Catenin and Inhibits Stem Cell Properties of Non-Small Cell Lung Carcinoma. Molecules. 2020 Jan 6;25(1):224. doi: 10.3390/molecules25010224. PMID: 31935827; PMCID: PMC6983151. 7: Baek SC, Ryu HW, Kang MG, Lee H, Park D, Cho ML, Oh SR, Kim H. Selective inhibition of monoamine oxidase A by chelerythrine, an isoquinoline alkaloid. Bioorg Med Chem Lett. 2018 Aug 1;28(14):2403-2407. doi: 10.1016/j.bmcl.2018.06.023. Epub 2018 Jun 18. PMID: 29925480. 8: Lin W, Huang J, Yuan Z, Feng S, Xie Y, Ma W. Protein kinase C inhibitor chelerythrine selectively inhibits proliferation of triple-negative breast cancer cells. Sci Rep. 2017 May 17;7(1):2022. doi: 10.1038/s41598-017-02222-0. PMID: 28515445; PMCID: PMC5435721. 9: Zhong M, Wang YH, Wang L, Long RQ, Chen CL. Preparation and application of magnetic molecularly imprinted polymers for the isolation of chelerythrine from Macleaya cordata. J Sep Sci. 2018 Aug;41(16):3318-3327. doi: 10.1002/jssc.201800245. Epub 2018 Jul 3. PMID: 29917314. 10: Hu B, Xu G, Zheng Y, Tong F, Qian P, Pan X, Zhou X, Shen R. Chelerythrine Attenuates Renal Ischemia/Reperfusion-induced Myocardial Injury by Activating CSE/H2S via PKC/NF-κB Pathway in Diabetic Rats. Kidney Blood Press Res. 2017;42(2):379-388. doi: 10.1159/000477948. Epub 2017 Jun 15. PMID: 28624831.