A β-carboline alkaloid and an active metabolite of harmaline
Related Products
Analytical Standard(s)
35145Harmalol
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Harmalol (hydrochloride hydrate)

Item No. 36090

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4,9-dihydro-1-methyl-3H-pyrido[3,4-b]indol-7-ol, monohydrochloride, dihydrate
CAS Number
6028-00-8
Synonyms
  • 11-hydroxy Harmalan
  • Harmidol
Molecular Formula
C12H12N2O • HCl [2H2O]
Formula Weight
272.7
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 1 mg/mlEthanol: 2 mg/ml
λmax
216, 386 nm
SMILES
OC1=CC=C2C(NC3=C2CCN=C3C)=C1.Cl.O.O
InChi Code
InChI=1S/C12H12N2O.ClH.2H2O/c1-7-12-10(4-5-13-7)9-3-2-8(15)6-11(9)14-12;;;/h2-3,6,14-15H,4-5H2,1H3;1H;2*1H2
InChi Key
OYKGNQNESCZSHQ-UHFFFAOYSA-N
Origin
Plant/Unspecified sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    100 mg

    $44

    Add

    250 mg

    $98

    Add

    500 mg

    $174

    Add

    1 g

    $304

    Add
    Kinase Resource Center
    Discover Products & Resources for Kinase Research
    • Kinase inhibitors, screening libraries, assay kits, & more
    • Tools to study kinase signaling pathways:
      • Growth factor signaling
      • PI3K/Akt/mTOR
      • MAPKs (ERK, p38, & JNK)
      • JAK/STAT signaling
    • Articles, resources, & advice
    EXPLORE NOW
    Product Description

    Harmalol is a β-carboline alkaloid and an active metabolite of harmaline that has been found in P. harmala and has diverse biological activities.1,2,3,4,5 It is an inhibitor of dual-specificity tyrosine phosphorylation-regulated kinase 1A (DYRK1A; IC50 = 0.63 µM) and monoamine oxidase A (MAO-A; IC50 = 0.66 µM).3 It is selective for DYRK1A over Cdk1, Cdk5, CK1α1, Clk4, DYRK2, Pim-1, and GSK3β but also inhibits DYRK1B and Clk1 at 10 µM. It inhibits proliferation of H4 human glioblastoma cells (IC50s = 23.7 µM). Harmalol (0.5-12.5 µM) reduces increases in the levels of the cytochrome P450 (CYP) isoform CYP1A1 induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in HepG2 cells and prevents TCDD-induced activation of the aryl hydrocarbon receptor (AhR) in guinea pig hepatic cytosolic extracts.4 It reduces glutamate-induced cytotoxicity, cytochrome c release, caspase-3 activation, and the production of reactive oxygen species (ROS) in PC12 cells when used at a concentration of 25 µM.5 This product is also available as an analytical reference standard (Item No. 35145).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Brierley, D.I., and Davidson, C. Developments in harmine pharmacology – implications for ayahuasca use and drug-dependence treatment. Prog. Neuropsychopharmacol. Biol. Psychiatry 39(2), 263-272 (2012).

    2. Nikam, T.D., Nitnaware, K.M., and Ahire, M.L. Alkaloids derived from tryptophan: Harmine and related alkaloids. Natural products. Phytochemistry, botany and metabolism of alkaloids, phenolics and terpenes 553-574 (2013).

    3. Tarpley, M., Oladapo, H.O., Strepay, D., et al. Identification of harmine and β-carboline analogs from a high-throughput screen of an approved drug collection; profiling as differential inhibitors of DYRK1A and monoamine oxidase A and for in vitro and in vivo anti-cancer studies. Eur. J. Pharm. Sci. 162, 105821 (2021).

    4. El Gendy, M.A.M., Soshilov, A.A., Denison, M.S., et al. Harmaline and harmalol inhibit the carcinogen-activating enzyme CYP1A1 via transcriptional and posttranslational mechanisms. Food Chem. Toxicol. 50(2), 353-362 (2012).

    5. Han, E.S., and Lee, C.S. Inhibition of glutamate-induced change in mitochondrial membrane permeability in PC12 cells by 1-methylated β-carbolines. Biomol. Ther. (Seoul) 11(2), 112-118 (2003).