Harmine hydrochloride

Description

Harmine (343-27-1) is a selective competitive and reversible inhibitor of MAO-A (IC50= 8 μM).1Harmine is a potent and specific inhibitor of both the kinase activity and autophosphorylation of tyrosine during translation DYRK1A (IC50‘s: DYRKA1A = 33 nM; DYRKA1B = 166 nM; DYRK2 = 1.9 μM; DYRK4 = 80 μM).2,3Inhibits self-renewal and promotes differentiation of glioblastoma stem-like cells (GSLC’s) possibly via inhibition of Akt phosphorylation.4Harmine has also been shown to possess antimicrobial, antifungal, antiplasmodial, antitumor, antioxidant, antimutagenic and antigenotoxic properties.5Inhibits osteoclast differentiation and bone resorption via downregulation of c-Fos and NFATc1 induced by RANKL.6

Chemical Properties

yellow to slightly green crystalline powder

Uses

Harmine Monohydrochloride is an anti-viral agents for the treatment of EV71 infection. It inhibits enterovirus 71 replication by targeting NF-κB pathway.

in vivo

IC 50

5-HT_2A Receptor: 397 nM (Ki); DYRK1A

Purification Methods

The hydrate crystallises as fluorescent crystals from water. The anhydrous salt has m 319o. [Beilstein 23/12 V 237.]

References

[1] WOUTERS J. Structural aspects of monoamine oxidase and its reversible inhibition.[J]. Current medicinal chemistry, 1998, 5 2: 137-162.
[2] ANNE SEIFERT  Paul R C  Lindsey A Allan. DYRK1A phosphorylates caspase 9 at an inhibitory site and is potently inhibited in human cells by harmine[J]. The FEBS journal, 2008, 275 24: 6268-6280. DOI:10.1111/j.1742-4658.2008.06751.x
[3] NORA GÖCKLER. Harmine specifically inhibits protein kinase DYRK1A and interferes with neurite formation[J]. The FEBS journal, 2009, 276 21: 6324-6337. DOI:10.1111/j.1742-4658.2009.07346.x
[4] HUAILEI LIU. Harmine hydrochloride inhibits Akt phosphorylation and depletes the pool of cancer stem-like cells of glioblastoma.[J]. Journal of Neuro-Oncology, 2013, 112 1: 39-48. DOI:10.1007/s11060-012-1034-x
[5] K PATEL . A review on medicinal importance, pharmacological activity and bioanalytical aspects of beta-carboline alkaloid “Harmine”[J]. Asian Pacific journal of tropical biomedicine, 2012, 2 8: Pages 660-664. DOI:10.1016/s2221-1691(12)60116-6
[6] TAKAYUKI YONEZAWA . Harmine, a β-carboline alkaloid, inhibits osteoclast differentiation and bone resorption in vitro and in vivo[J]. European journal of pharmacology, 2011, 650 2: Pages 511-518. DOI:10.1016/j.ejphar.2010.10.048