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Chemical Structure
Chemical Structure
Chemical Structure

Harmine [442-51-3]

Research Use Only
AG-CN2-0510
AdipoGen Life Sciences
CAS Number442-51-3
Product group Chemicals
Estimated Purity>98%
Molecular Weight212.3
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    Harmine
  • Delivery Days Customer
    10
  • CAS Number
    442-51-3
  • Certification
    Research Use Only
  • Estimated Purity
    >98%
  • Hazard Information
    Warning
  • Molecular Formula
    C13H12N2O
  • Molecular Weight
    212.3
  • Scientific Description
    Chemical. CAS: 442-51-3. Formula: C13H12N2O. MW: 212.3. Synthetic. Originally isolated from the seeds of Peganum harmala (Syrian rue). Fluorescent beta-carboline alkaloid. Potent ATP-competitive and selective inhibitor of DYRK1A, DYRK2 and DYRK3 with IC50 values of 0.08, 0.9 and 0.8microM. Shown to inhibit CLK2, PIM3 (at 4.3microM) and CK1 at 1.5microM as well. Inhibits DYRK1A-mediated tau phosphorylation. Competitive and reversible monoamine oxidase inhibitor (MAOI) that reversibly inhibits MAO-A (monoamine oxidase A) but has no effect on MAO-B. Acetylcholinesterase inhibitor (AChEI). Could potentially ameliorate impaired memory. Useful fluorescent pH indicator. Shows a color change from pH 7.2 (blue fluorescence) to pH 8.9 (yellow fluorescence). With the radioisotope carbon-11, used in positron emission tomography neuroimaging to examine its binding to MAO-A. Antiviral and antileishmanial compound. Antiangiogenic and antitumor agent. Inhibits cellular proliferation, migration, invasion and induced apoptosis in vitro, as well as inhibited tumor growth in vivo. Antidiabetic. Unique regulator of PPARgamma expression that acts by inhibiting the Wnt signaling pathway in a cell-specific manner. Induces pancreatic beta-cell proliferation. Reduced blood glucose, free fatty acids and triglyceride levels, delayed hyperglycemia and improved insulin sensitivity. Shown to induce adipocyte thermogenesis through the RAC1-MEK-ERK-CHD4 axis. CHD4 directly binds the proximal promoter region of UCP1, serving as a negative modulator of UCP1 and inducing browing in brown (BAT) and white adipose tissue (WAT). Inhibits DNA topoisomerases and interferes with DNA synthesis. Interacts with DNA via both groove binding and intercalative modes and cause major DNA structural changes. Shown to promote differentiation of osteoblasts (bone-forming cells) and chondrocytes (cells in the cartilage) and to inhibit osteoclastogenesis (the formation of bone resorbing cells). Antimalarial by inhibiting the Plasmodium falciparum heat shock protein 90 (PfHSP90) ATP-binding domain. - Fluorescent beta-carboline alkaloid. Potent ATP-competitive and selective inhibitor of DYRK1A, DYRK2 and DYRK3 with IC50 values of 0.08, 0.9 and 0.8microM. Shown to inhibit CLK2, PIM3 (at 4.3microM) and CK1 at 1.5microM as well. Inhibits DYRK1A-mediated tau phosphorylation. Competitive and reversible monoamine oxidase inhibitor (MAOI) that reversibly inhibits MAO-A (monoamine oxidase A) but has no effect on MAO-B. Acetylcholinesterase inhibitor (AChEI). Could potentially ameliorate impaired memory. Useful fluorescent pH indicator. Shows a color change from pH 7.2 (blue fluorescence) to pH 8.9 (yellow fluorescence). With the radioisotope carbon-11, used in positron emission tomography neuroimaging to examine its binding to MAO-A. Antiviral and antileishmanial compound. Antiangiogenic and antitumor agent. Inhibits cellular proliferation, migration, invasion and induced apoptosis in vitro, as well as inhibited tumor growth in vivo. Antidiabetic. Unique regulator of PPARgamma expression that acts by inhibiting the Wnt signaling pathway in a cell-specific manner. Induces pancreatic beta-cell proliferation. Reduced blood glucose, free fatty acids and triglyceride levels, delayed hyperglycemia and improved insulin sensitivity. Shown to induce adipocyte thermogenesis through the RAC1-MEK-ERK-CHD4 axis. CHD4 directly binds the proximal promoter region of UCP1, serving as a negative modulator of UCP1 and inducing browning in brown (BAT) and white adipose tissue (WAT). Inhibits DNA topoisomerases and interferes with DNA synthesis. Interacts with DNA via both groove binding and intercalative modes and cause major DNA structural changes. Shown to promote differentiation of osteoblasts (bone-forming cells) and chondrocytes (cells in the cartilage) and to inhibit osteoclastogenesis (the formation of bone resorbing cells). Antimalarial by inhibiting the Plasmodium falciparum heat shock protein 90 (PfHSP90) ATP-binding domain.
  • SMILES
    CC1=NC=CC2=C1NC3=C2C=CC(OC)=C3
  • Storage Instruction
    -20°C,2°C to 8°C
  • UNSPSC
    12352200

References

  • The pH-dependence of the absorption and fluorescence spectra of harmine and harmol: drastic differences in the tautomeric equilibria of ground and first excited singlet state: O.S. Wolfbeis & E. Furlinger; Z. Physik. Chem. 129, 171 (1982)
  • Antiviral effect of harmine, a photoactive beta-carboline alkaloid: J.B. Hudson, et al.; Photochem. Photobiol. 43, 21 (1986)
  • Harmine as a substitute for 33258 Hoechst in the FPG technique: M.G. Gutierrez-Gonzalvez, et al.; Histochemistry 89, 199 (1988)
  • Effect of moclobemide on rat brain monoamine oxidase A and B: comparison with harmaline and clorgyline: J. Gerardy; Prog. Neuropsychopharmacol. Biol. Psychiatry 18, 793 (1994)
  • 11C-harmine as a tracer for monoamine oxidase A (MAO-A): in vitro and in vivo studies: M. Bergstrom, et al.; Nucl. Med. Biol. 24, 287 (1997)
  • Antitumor agents 201. Cytotoxicity of harmine and beta-carboline analogs: J. Ishida, et al.; Bioorg. Med. Chem. Lett. 9, 3319 (1999)
  • Harmine: evaluation of its antileishmanial properties in various vesicular delivery systems: S. Lala, et al.; J. Drug Target 12, 165 (2004)
  • The small molecule harmine is an antidiabetic cell-type-specific regulator of PPARgamma expression: H. Waki, et al.; Cell Metab. 5, 357 (2007)
  • The selectivity of protein kinase inhibitors: a further update: J. Bain, et al.; Biochem. J. 408, 297 (2007)
  • DYRK1A phosphorylates caspase 9 at an inhibitory site and is potently inhibited in human cells by harmine: A. Seifert, et al.; FEBS J. 275, 6268 (2008)