Harmalol HCl hydrate
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MedKoo CAT#: 112010

CAS#: 6028-00-8

Description: Harmalol HCl hydrate is a β-carboline alkaloid and an active metabolite of harmaline that has been found in P. harmala and has diverse biological activities. 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). 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. 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. This product is also available as an analytical reference standard.

Chemical Structure

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Harmalol HCl hydrate
CAS# 6028-00-8
Instruction

Theoretical Analysis

MedKoo Cat#: 112010
Name: Harmalol HCl hydrate
CAS#: 6028-00-8
Chemical Formula: C12H17ClN2O3
Exact Mass: 0.00
Molecular Weight: 272.730
Elemental Analysis: C, 52.85; H, 6.28; Cl, 13.00; N, 10.27; O, 17.60

Price and Availability

Size Price Availability Quantity
100mg USD 250 2 Weeks
250mg USD 500 2 Weeks
500mg USD 850 2 Weeks
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Synonym: 11-hydroxy Harmalan; Harmidol; Harmalol; Harmalol hydrochloride hydrate; 11hydroxy Harmalan; 11 hydroxy Harmalan

IUPAC/Chemical Name: 1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indol-7-ol hydrochloride dihydrate

InChi Key: OYKGNQNESCZSHQ-UHFFFAOYSA-N

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

SMILES Code: OC1=CC=C2C(NC3=C2CCN=C3C)=C1.Cl.O.O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Product Data:
Product Data
Instruction:
View handling instruction

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 10.0 36.67
DMSO 1.0 3.67
Ethanol 2.0 7.33

Preparing Stock Solutions

The following data is based on the product molecular weight 272.730000000000000000000000000000 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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PMID: 30970283. 6: Ghosh T, Sarkar S, Bhattacharjee P, Jana GC, Hossain M, Pandya P, Bhadra K. In vitro relationship between serum protein binding to beta-carboline alkaloids: a comparative cytotoxic, spectroscopic and calorimetric assays. J Biomol Struct Dyn. 2020 Mar;38(4):1103-1118. doi: 10.1080/07391102.2019.1595727. Epub 2019 Apr 4. PMID: 30909826. 7: Kadam NS, Naik AA, Doshi PJ, Nikam TD. High-Performance Thin-Layer Chromatography Method for Simultaneous Determination of Antipsychotic and Medicinally Important Five β-Carboline Alkaloids. J Chromatogr Sci. 2019 Apr 1;57(4):312-322. doi: 10.1093/chromsci/bmy113. PMID: 30608572. 8: Sarkar S, Bhadra K. Therapeutic Role of Harmalol Targeting Nucleic Acids: Biophysical Perspective and in vitro Cytotoxicity. Mini Rev Med Chem. 2018;18(19):1624-1639. doi: 10.2174/1389557518666171211164830. PMID: 29231137. 9: Hamid HA, Ramli AN, Yusoff MM. Indole Alkaloids from Plants as Potential Leads for Antidepressant Drugs: A Mini Review. Front Pharmacol. 2017 Feb 28;8:96. doi: 10.3389/fphar.2017.00096. PMID: 28293192; PMCID: PMC5328930. 10: Santos MC, Navickiene S, Gaujac A. Determination of Tryptamines and β-Carbolines in Ayahuasca Beverage Consumed During Brazilian Religious Ceremonies. J AOAC Int. 2017 May 1;100(3):820-824. doi: 10.5740/jaoacint.16-0337. Epub 2017 Jan 19. PMID: 28105971. 11: Tascon M, Gagliardi LG, Benavente F. Parts-per-trillion detection of harmala alkaloids in Undaria pinnatifida algae by on-line solid phase extraction capillary electrophoresis mass spectrometry. Anal Chim Acta. 2017 Feb 15;954:60-67. doi: 10.1016/j.aca.2016.12.012. Epub 2016 Dec 26. PMID: 28081815. 12: Olmedo GM, Cerioni L, González MM, Cabrerizo FM, Rapisarda VA, Volentini SI. Antifungal activity of β-carbolines on Penicillium digitatum and Botrytis cinerea. Food Microbiol. 2017 Apr;62:9-14. doi: 10.1016/j.fm.2016.09.011. Epub 2016 Sep 16. PMID: 27889171. 13: Sarkar S, Bhattacharjee P, Bhadra K. DNA binding and apoptotic induction ability of harmalol in HepG2: Biophysical and biochemical approaches. Chem Biol Interact. 2016 Oct 25;258:142-52. doi: 10.1016/j.cbi.2016.08.024. Epub 2016 Aug 31. PMID: 27590872. 14: Tascon M, Benavente F, Castells CB, Gagliardi LG. Quality criterion to optimize separations in capillary electrophoresis: Application to the analysis of harmala alkaloids. J Chromatogr A. 2016 Aug 19;1460:190-6. doi: 10.1016/j.chroma.2016.07.032. Epub 2016 Jul 14. PMID: 27443250. 15: Tascón M, Benavente F, Vizioli NM, Gagliardi LG. A rapid and simple method for the determination of psychoactive alkaloids by CE-UV: application to Peganum Harmala seed infusions. Drug Test Anal. 2017 Apr;9(4):596-602. doi: 10.1002/dta.1989. Epub 2016 Jul 5. PMID: 27377797. 16: Ibraheem ZO, Abdul Majid R, Mohd Noor S, Mohd Sidek H, Basir R. The Potential of β Carbolin Alkaloids to Hinder Growth and Reverse Chloroquine Resistance in Plasmodium falciparum. 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Sequence specific binding of beta carboline alkaloid harmalol with deoxyribonucleotides: binding heterogeneity, conformational, thermodynamic and cytotoxic aspects. PLoS One. 2014 Sep 23;9(9):e108022. doi: 10.1371/journal.pone.0108022. PMID: 25247695; PMCID: PMC4172587.