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MedKoo Cat#: 128735 | Name: Demethyleneberberine

Description:

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

Demethyleneberberine is an isoquinoline alkaloid that has been found in P. chinensis and has diverse biological activities.

Chemical Structure

Demethyleneberberine
Demethyleneberberine
CAS#25459-91-0 (cation)

Theoretical Analysis

MedKoo Cat#: 128735

Name: Demethyleneberberine

CAS#: 25459-91-0 (cation)

Chemical Formula: C19H18NO4+

Exact Mass: 324.1230

Molecular Weight: 324.36

Elemental Analysis: C, 70.36; H, 5.59; N, 4.32; O, 19.73

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 #
16705-03-6 (chloride) 60373-80-0 (bromide) 19799-04-3 (iodide) 25459-91-0 (cation)
Synonym
Demethyleneberberine; DMB; DM-BBR; 2-Hydroxyjatrorrhizine
IUPAC/Chemical Name
2,3-dihydroxy-9,10-dimethoxy-5,6-dihydroisoquinolino[3,2-a]isoquinolin-7-ium
InChi Key
HVTCKKMWZDDWOY-UHFFFAOYSA-O
InChi Code
InChI=1S/C19H17NO4/c1-23-18-4-3-11-7-15-13-9-17(22)16(21)8-12(13)5-6-20(15)10-14(11)19(18)24-2/h3-4,7-10,22H,5-6H2,1-2H3/p+1
SMILES Code
OC1=C(O)C=C2CC[N+]3=CC4=C(OC)C(OC)=CC=C4C=C3C2=C1
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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 324.36 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: Saklani P, Khan H, Singh TG, Gupta S, Grewal AK. Demethyleneberberine, a potential therapeutic agent in neurodegenerative disorders: a proposed mechanistic insight. Mol Biol Rep. 2022 Oct;49(10):10101-10113. doi: 10.1007/s11033-022-07594-9. Epub 2022 Jun 3. PMID: 35657450. 2: Li J, Zhang Q, Chen Y, Lu C, Tong Y. Pharmacokinetics, Tissue Distribution and Excretion of Demethyleneberberine, a Metabolite of Berberine, in Rats and Mice. Molecules. 2023 Nov 23;28(23):7725. doi: 10.3390/molecules28237725. PMID: 38067456; PMCID: PMC10708275. 3: Gupta S, Khan A, Vishwas S, Gulati M, Gurjeet Singh T, Dua K, Kumar Singh S, Najda A, Sayed AA, Almeer R, Abdel-Daim MM. Demethyleneberberine: A possible treatment for Huntington's disease. Med Hypotheses. 2021 Aug;153:110639. doi: 10.1016/j.mehy.2021.110639. Epub 2021 Jun 29. PMID: 34229236. 4: Zhao Y, Liu P, Luan H, Jiang H, Xu Y, Zhang Y, Zhang Y, Li R. Demethyleneberberine alleviated the inflammatory response by targeting MD-2 to inhibit the TLR4 signaling. Front Immunol. 2023 Apr 24;14:1130404. doi: 10.3389/fimmu.2023.1130404. PMID: 37168866; PMCID: PMC10165096. 5: Wang T, Yang XC, Ding Y, Zhang YJ, Ru YQ, Tan JJ, Xu F, Gao WW, Xia YM. Cuprous oxide-demethyleneberberine nanospheres for single near-infrared light- triggered photoresponsive-enhanced enzymatic synergistic antibacterial therapy. J Mater Chem B. 2023 Feb 22;11(8):1760-1772. doi: 10.1039/d2tb02594a. PMID: 36723366. 6: Wang Z, Wang L, Shi B, Sun X, Xie Y, Yang H, Zi C, Wang X, Sheng J. Demethyleneberberine promotes apoptosis and suppresses TGF-β/Smads induced EMT in the colon cancer cells HCT-116. Cell Biochem Funct. 2021 Aug;39(6):763-770. doi: 10.1002/cbf.3638. Epub 2021 May 24. PMID: 34028068. 7: Zhao Y, Liu P, Zhang Y, Jiang H, Luan H, Xu Y, Zhang Y, Li R. Demethyleneberberine blocked the maturation of IL-1β in inflammation by inhibiting TLR4-mitochondria signaling. Int Immunopharmacol. 2022 Dec;113(Pt A):109319. doi: 10.1016/j.intimp.2022.109319. Epub 2022 Oct 17. PMID: 36252484. 8: Tao C, Hu SQ, Chen J, Chen YJ, Sun KH, Cui GZ, Ma M, Wu ZZ. Highly efficient synthesis and monoamine oxidase B inhibitory profile of demethyleneberberine, columbamine and palmatine. Neurochem Int. 2020 Oct;139:104807. doi: 10.1016/j.neuint.2020.104807. Epub 2020 Jul 22. PMID: 32711021. 9: Qiang X, Xu L, Zhang M, Zhang P, Wang Y, Wang Y, Zhao Z, Chen H, Liu X, Zhang Y. Demethyleneberberine attenuates non-alcoholic fatty liver disease with activation of AMPK and inhibition of oxidative stress. Biochem Biophys Res Commun. 2016 Apr 15;472(4):603-9. doi: 10.1016/j.bbrc.2016.03.019. Epub 2016 Mar 9. PMID: 26970305. 10: Wang Y, Zhao Z, Yan Y, Qiang X, Zhou C, Li R, Chen H, Zhang Y. Demethyleneberberine Protects against Hepatic Fibrosis in Mice by Modulating NF- κB Signaling. Int J Mol Sci. 2016 Jun 30;17(7):1036. doi: 10.3390/ijms17071036. PMID: 27376272; PMCID: PMC4964412. 11: Zhang M, Li Q, Zhou C, Zhao Y, Li R, Zhang Y. Demethyleneberberine attenuates concanavalin A-induced autoimmune hepatitis in mice through inhibition of NF-κB and MAPK signaling. Int Immunopharmacol. 2020 Mar;80:106137. doi: 10.1016/j.intimp.2019.106137. Epub 2020 Jan 10. PMID: 31931366. 12: Liu J, Huang X, Liu D, Ji K, Tao C, Zhang R, Chen J. Demethyleneberberine induces cell cycle arrest and cellular senescence of NSCLC cells via c-Myc/HIF-1α pathway. Phytomedicine. 2021 Oct;91:153678. doi: 10.1016/j.phymed.2021.153678. Epub 2021 Jul 18. PMID: 34385092. 13: Zhang P, Qiang X, Zhang M, Ma D, Zhao Z, Zhou C, Liu X, Li R, Chen H, Zhang Y. Demethyleneberberine, a natural mitochondria-targeted antioxidant, inhibits mitochondrial dysfunction, oxidative stress, and steatosis in alcoholic liver disease mouse model. J Pharmacol Exp Ther. 2015 Jan;352(1):139-47. doi: 10.1124/jpet.114.219832. Epub 2014 Oct 31. PMID: 25362106. 14: Han Y, Ge C, Ye J, Li R, Zhang Y. Demethyleneberberine alleviates Pseudomonas aeruginosa-induced acute pneumonia by inhibiting the AIM2 inflammasome and oxidative stress. Pulm Pharmacol Ther. 2023 Dec;83:102259. doi: 10.1016/j.pupt.2023.102259. Epub 2023 Sep 17. PMID: 37726074. 15: Chen YY, Li RY, Shi MJ, Zhao YX, Yan Y, Xu XX, Zhang M, Zhao XT, Zhang YB. Demethyleneberberine alleviates inflammatory bowel disease in mice through regulating NF-κB signaling and T-helper cell homeostasis. Inflamm Res. 2017 Feb;66(2):187-196. doi: 10.1007/s00011-016-1005-3. Epub 2016 Nov 29. PMID: 27900412. 16: Ge C, Huang M, Han Y, Shou C, Li D, Zhang Y. Demethyleneberberine Alleviates Pulmonary Fibrosis through Disruption of USP11 Deubiquitinating GREM1. Pharmaceuticals (Basel). 2024 Feb 22;17(3):279. doi: 10.3390/ph17030279. PMID: 38543064; PMCID: PMC10974697.