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MedKoo Cat#: 112010 | Name: Harmalol HCl hydrate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Harmalol HCl hydrate
Harmalol HCl hydrate
CAS#6028-00-8

Theoretical Analysis

MedKoo Cat#: 112010

Name: Harmalol HCl hydrate

CAS#: 6028-00-8

Chemical Formula: C12H17ClN2O3

Exact Mass: 0.0000

Molecular Weight: 272.73

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 250.00 2 Weeks
250mg USD 500.00 2 Weeks
500mg USD 850.00 2 Weeks
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Related CAS #
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Synonym
Harmalol hydrochloride dihydrate; Harmalol HCl hydrate; Harmalol (hydrochloride hydrate); 11-hydroxy Harmalan; 11 hydroxy Harmalan; Harmidol
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
More Info
Solvent mg/mL mM
Solubility
DMF 10.0 36.67
DMSO 1.0 3.67
Ethanol 2.0 7.33
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 272.73 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
1: Gonçalves J, Castilho M, Rosado T, Luís Â, Restolho J, Fernández N, Gallardo E, Duarte AP. In Vitro Study of the Bioavailability and Bioaccessibility of the Main Compounds Present in Ayahuasca Beverages. Molecules. 2021 Sep 13;26(18):5555. doi: 10.3390/molecules26185555. PMID: 34577025; PMCID: PMC8470438. 2: Sharifi-Rad J, Quispe C, Herrera-Bravo J, Semwal P, Painuli S, Özçelik B, Hacıhasanoğlu FE, Shaheen S, Sen S, Acharya K, Amirian M, Castillo CMS, López MD, Schoebitz M, Martorell M, Goloshvili T, Al-Harrasi A, Al-Rawahi A, Kumar M, Suleria HAR, Cho WC. Peganum spp.: A Comprehensive Review on Bioactivities and Health-Enhancing Effects and Their Potential for the Formulation of Functional Foods and Pharmaceutical Drugs. Oxid Med Cell Longev. 2021 Jun 27;2021:5900422. doi: 10.1155/2021/5900422. PMID: 34257813; PMCID: PMC8260309. 3: Tedesco P, Beraldo P, Massimo M, Fioravanti ML, Volpatti D, Dirks R, Galuppi R. Comparative Therapeutic Effects of Natural Compounds Against Saprolegnia spp. (Oomycota) and Amyloodinium ocellatum (Dinophyceae). Front Vet Sci. 2020 Feb 21;7:83. doi: 10.3389/fvets.2020.00083. PMID: 32154278; PMCID: PMC7047137. 4: Biggi S, Pancher M, Stincardini C, Luotti S, Massignan T, Dalle Vedove A, Astolfi A, Gatto P, Lolli G, Barreca ML, Bonetto V, Adami V, Biasini E. Identification of compounds inhibiting prion replication and toxicity by removing PrPC from the cell surface. J Neurochem. 2020 Jan;152(1):136-150. doi: 10.1111/jnc.14805. Epub 2019 Jul 18. PMID: 31264722. 5: Wang Y, Wang H, Zhang L, Zhang Y, Sheng Y, Deng G, Li S, Cao N, Guan H, Cheng X, Wang C. Subchronic toxicity and concomitant toxicokinetics of long-term oral administration of total alkaloid extracts from seeds of Peganum harmala Linn: A 28-day study in rats. J Ethnopharmacol. 2019 Jun 28;238:111866. doi: 10.1016/j.jep.2019.111866. Epub 2019 Apr 7. 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. Iran J Parasitol. 2015 Oct- Dec;10(4):577-83. PMID: 26811724; PMCID: PMC4724834. 17: Bhattacharjee P, Sarkar S, Pandya P, Bhadra K. Targeting different RNA motifs by beta carboline alkaloid, harmalol: a comparative photophysical, calorimetric, and molecular docking approach. J Biomol Struct Dyn. 2016 Dec;34(12):2722-2740. doi: 10.1080/07391102.2015.1126694. Epub 2016 Jun 6. PMID: 26629671. 18: Sarkar S, Bhadra K. Corrigendum to "Binding of alkaloid harmalol to DNA: Photophysical and calorimetric approach" [J. Photochem. Photobiol. B: Biol. 130 (2014) 272-280]. J Photochem Photobiol B. 2015 Jul;148:366. doi: 10.1016/j.jphotobiol.2015.03.003. Epub 2015 Apr 15. PMID: 28629801. 19: Tascon M, Benavente F, Sanz-Nebot VM, Gagliardi LG. Fast determination of harmala alkaloids in edible algae by capillary electrophoresis mass spectrometry. Anal Bioanal Chem. 2015 May;407(13):3637-45. doi: 10.1007/s00216-015-8579-4. Epub 2015 Mar 8. PMID: 25749794. 20: Sarkar S, Pandya P, Bhadra K. 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.

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KZN 00737

KZN 00737

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