Harmine - CAS 442-51-3
Catalog number: 442-51-3
Category: Inhibitor
Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Molecular Formula:
C13H12N2O
Molecular Weight:
212.25
COA:
Inquire
Targets:
5-HT Receptor | Microtubule/Tubulin | Tau
Description:
Harmine induces apoptosis and inhibits proliferation, migration and invasion of human gastric cancer cells, which may be mediated by down-regulation of COX-2 expression.
Purity:
≥98 %
Appearance:
Off-White to Brown-Orange Solid
Synonyms:
7-Methoxy-1-methyl-9H-beta-carbolin; 7-Methoxy-1-methyl-9H-beta-carboline
Solubility:
Soluble in DMSO
Storage:
Store at 2-8 °C
MSDS:
Inquire
Application:
Potent and selective inhibitor of DYRK1A
Quality Standard:
Enterprise Standard
Shelf Life:
As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
Quantity:
Milligrams-Grams
Melting Point:
>164 ºC
InChIKey:
BXNJHAXVSOCGBA-UHFFFAOYSA-N
InChI:
1S/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3
Canonical SMILES:
CC1=NC=CC2=C1NC3=C2C=CC(=C3)OC
1.Synthesis, cytotoxic, anti-lipoxygenase and anti-acetylcholinesterase capacities of novel derivatives from harmine.
Filali I1,2, Belkacem MA1,2, Ben Nejma A1, Souchard JP2, Ben Jannet H1, Bouajila J2. J Enzyme Inhib Med Chem. 2016 Mar 30:1-11. [Epub ahead of print]
We synthesized two series of new hydrazide harmine derivatives. The reaction of harmine 1 with ethyl acetate chloride afforded the corresponding ethyl ester 2. The treatment of 2 with hydrazine hydrate gave the hydrazide 3 which further converted into hydrazones 4a-j and dihydrazides 5a-c. A series of new triazoles 7a-f has also been prepared from the suitable propargyl harmine 6. The synthesized derivatives were characterized by 1H-NMR, 13C-NMR, and HRMS and evaluated for their activities against MCF7, HCT116 OVCAR-3, acetylcholinesterase and 5-lipoxygenase. The most hydrazones derivatives 4a-j have a good cytotoxic activity against all cell lines, when 4a, 4d, 4f and 4 g are more active than 1 (against OVCAR-3 IC50 16.7-2.5 μM). The compound 6 was the most active (IC50 = 1.9 μM) against acetylcholinesterase. Some compounds exhibited significant activity against 5-lipoxygenase (IC50 = 30.9-63.1 μM).
2.Harmine induces cell cycle arrest and mitochondrial pathway-mediated cellular apoptosis in SW620 cells via inhibition of the Akt and ERK signaling pathways.
Liu J1, Li Q1, Liu Z1, Lin L1, Zhang X2, Cao M1, Jiang J2. Oncol Rep. 2016 Mar 21. doi: 10.3892/or.2016.4695. [Epub ahead of print]
Harmine, a β-carboline alkaloid isolated from the seeds of Peganum harmala, possesses both antitumor and anti‑nociceptive effects and inhibits human DNA topoisomerase. However, no detailed data are available concerning the mechanisms of harmine in human colorectal carcinoma SW620 cells. In the present study, we demonstrated that harmine inhibited the proliferation of SW620 cells in a dose-dependent manner using MTT and clone formation assays, and the IC50 value of harmine on the growth inhibition of SW620 cells for 48 h was 5.13 µg/ml. PI staining showed that harmine altered the cell cycle distribution by decreasing the proportion of cells in the G0-G1 phase and increasing the proportion in the S and G2-M phase. The expression level of cyclin D1 was decreased, while the expression of cyclin A, E2 and B1, CDK1/cdc2, Myt-1 and p-cdc2 (Tyr15) were increased, which was in accordance with the S and G2/M phase arrest. Hoechst 33258 staining revealed nuclear fragmentation, chromosomal condensation and cell shrinkage in the SW620 cells treated with harmine.
3.Pharmacokinetic study of harmane and its 10 metabolites in rat after intravenous and oral administration by UPLC-ESI-MS/MS.
Li S1,2, Teng L1,2, Liu W1, Cheng X1,3, Jiang B1, Wang Z1,3, Wang CH1,3. Pharm Biol. 2016 Jan 5:1-14. [Epub ahead of print]
Context The β-carboline alkaloid harmane is widely distributed in common foods, beverages and hallucinogenic plants. Harmane exerts potential in therapies for Alzheimer's and depression diseases. However, little information on its dynamic metabolic profiles and pharmacokinetics in vivo is currently available. Objective This study investigates the dynamic metabolic profiles and pharmacokinetic properties of harmane and its metabolites in rats in vivo. Materials and methods A highly selective, sensitive and rapid ultra-performance liquid chromatography combined with electrospray ionization tandem mass spectrometry (UPLC-ESI-MS/MS) method was developed and well-validated for simultaneous quantitative determination of harmane and its uncertain endogenous metabolite harmine, as well as for semiquantitative determination of 10 harmane metabolites in rats after intravenous injection and oral administration of harmane at 1.0 and 30.0 mg/kg, respectively.
4.Design and synthesis of C3-tethered 1,2,3-triazolo-β-carboline derivatives: Anticancer activity, DNA-binding ability, viscosity and molecular modeling studies.
Shankaraiah N1, Jadala C2, Nekkanti S2, Senwar KR2, Nagesh N3, Shrivastava S4, Naidu VG4, Sathish M5, Kamal A6. Bioorg Chem. 2016 Feb;64:42-50. doi: 10.1016/j.bioorg.2015.11.005. Epub 2015 Nov 23.
A series of new DNA-interactive C3-tethered 1,2,3-triazolo-β-carboline derivatives have been synthesized via 'click' reaction and evaluated for their in vitro cytotoxicity as well as DNA binding affinity. Interestingly, these hybrids have displayed potent in vitro cytotoxicity in comparison to Harmine against the HT-29 (colon cancer) and HGC-27 (gastric cancer) cell lines. The compounds 7f, 7k, 7n and 7s appear to be more effective against the HGC-27 cell line, among which compound 7f showed the highest cytotoxicity (5.44±0.58, IC50 μM). The compounds 7e and 7f appear to be more active against the HT-29 cell line, among which compound 7f exhibited the highest cytotoxicity (3.67±0.62, IC50 μM). To gain more insight into the DNA-binding ability, spectroscopic techniques such as UV-Visible, fluorescence and circular dichroism studies were performed. Viscosity measurements and molecular docking studies substantiate that these compounds indeed bind to DNA via the minor groove.
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CAS 442-51-3 Harmine

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