Harmalacidine

CAS# 26579-69-1

Harmalacidine

Catalog No. BCN8033----Order now to get a substantial discount!

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Quality Control of Harmalacidine

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Chemical structure

Harmalacidine

3D structure

Chemical Properties of Harmalacidine

Cas No. 26579-69-1 SDF Download SDF
PubChem ID 179484 Appearance Powder
Formula C12H12N2O2 M.Wt 216.24
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 7-methoxy-2,3,4,9-tetrahydropyrido[3,4-b]indol-1-one
SMILES COC1=CC2=C(C=C1)C3=C(N2)C(=O)NCC3
Standard InChIKey MWEGNYFSTKOOSD-UHFFFAOYSA-N
Standard InChI InChI=1S/C12H12N2O2/c1-16-7-2-3-8-9-4-5-13-12(15)11(9)14-10(8)6-7/h2-3,6,14H,4-5H2,1H3,(H,13,15)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Harmalacidine

The seed of Peganum harmala

Biological Activity of Harmalacidine

Description1. Harmalacidine exhibits cytotoxicity against U-937 cells with IC50 value of 3.1 ± 0.2 μmol/L, the mechanism is targeting the mitochondrial and protein tyrosine kinase signaling pathways (PTKs-Ras/Raf/ERK).
TargetsERK | Raf

Harmalacidine Dilution Calculator

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Harmalacidine Molarity Calculator

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Preparing Stock Solutions of Harmalacidine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.6245 mL 23.1225 mL 46.2449 mL 92.4898 mL 115.6123 mL
5 mM 0.9249 mL 4.6245 mL 9.249 mL 18.498 mL 23.1225 mL
10 mM 0.4624 mL 2.3122 mL 4.6245 mL 9.249 mL 11.5612 mL
50 mM 0.0925 mL 0.4624 mL 0.9249 mL 1.8498 mL 2.3122 mL
100 mM 0.0462 mL 0.2312 mL 0.4624 mL 0.9249 mL 1.1561 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Harmalacidine

Cytotoxicity of alkaloids isolated from Peganum harmala seeds.[Pubmed:23811445]

Pak J Pharm Sci. 2013 Jul;26(4):699-706.

ETHNOPHARMACOLOGICAL RELEVANCE: Peganum harmala is used in traditional medicine to treat a number of diseases including cancer. Our preliminary studies show that the alkaloidal extract of PH seed is cytotoxic to several tumor cell lines in vitro and has antitumor effect in a tumor model in vivo. The present investigation was aimed at extending our previous studies in identifying the components in P. harmala seed-extract responsible for the cytotoxic effects, and study the cytotoxic and antiproliferative activity of isolated alkaloids and total alkaloidal fraction (TAF) in several tumor cell lines. Four alkaloids: harmalicidine, harmine, peganine (vasicine) and vasicinone were isolated from the P. harmala seed-extract and their activity and that of TAF were tested a) for their cytotoxic activity against four tumor cell lines [three developed by us by chemical-induction in Wistar rats: 1) Med-mek carcinoma ; 2) UCP-med carcinoma ; 3) UCP-med sarcoma] ; and 4) SP2/O-Ag14, and b) for antiproliferative effect on cells of Jurkat, E6-1 clone (inhibition of incorporation of {(3)H-thymidine} in cellular DNA). The alkaloids and TAF inhibited the growth of tumor cell lines to varying degrees; Sp2/O-Ag14 was the most sensitive, with IC50 values (concentration of the active substance that inhibited the growth of the tumor cells by 50%) ranging between 2.43 mug/mL and 19.20 mug/mL, while UCP-med carcinoma was the least sensitive (range of IC50 = 13.83 mug/mL to 59.97 mug/mL). Of the substances evaluated, harmine was the most active compound (IC50 for the 4 tumor cell lines varying between 2.43 mug/mL and 18.39 mug/mL), followed by TAF (range of IC50 = 7.32 mug/mL to 13.83 mug/mL); peganine was the least active (IC50 = 50 mug/mL to > 100 mug/mL). In terms of antiproliferative effect, vasicinone and TAF were more potent than other substances: the concentration of vasicinone, and TAF needed to inhibit the incorporation of {(3)H-TDR} in the DNA cells of Jurkat, E6-1 clone by 50% (IC50) were 8.60 +/- 0.023 mug/mL and 8.94 +/- 0.017 mug/mL, respectively, while peganine was the least active (IC50 >100 mug/mL). The IC50 values for Harmalacidine (27.10 +/- 0.011 mug/mL) and harmine (46.57 +/- 0.011 mug/mL) were intermediate. The harmala alkaloids inhibited the growth of four tumor cell lines, and proliferation of Jurkat cells with varying potencies. Harmine was the most potent in inhibiting cell growth, and vasicinone was most active as antiproliferating substance. The TAF had significant cytotoxic as well as antiproliferating activity.

Cytotoxic indole alkaloids against human leukemia cell lines from the toxic plant Peganum harmala.[Pubmed:26540074]

Toxins (Basel). 2015 Nov 3;7(11):4507-18.

Bioactivity-guided fractionation was used to determine the cytotoxic alkaloids from the toxic plant Peganum harmala. Two novel indole alkaloids, together with ten known ones, were isolated and identified. The novel alkaloids were elucidated to be 2-(indol-3-yl)ethyl-alpha-L-rhamnopyranosyl-(1 --> 6)-beta-D-glucopyranoside (2) and 3-hydroxy-3-(N-acetyl-2-aminoethyl)-6-methoxyindol-2-one (3). The cytotoxicity against human leukemia cells was assayed for the alkaloids and some of them showed potent activity. Harmalacidine (compound 8, HMC) exhibited the highest cytotoxicity against U-937 cells with IC50 value of 3.1 +/- 0.2 mumol/L. The cytotoxic mechanism of HMC was targeting the mitochondrial and protein tyrosine kinase signaling pathways (PTKs-Ras/Raf/ERK). The results strongly demonstrated that the alkaloids from Peganum harmala could be a promising candidate for the therapy of leukemia.

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