| Description | Harmalol hydrochloride (Harmidol hydrochloride) is a β-carboline alkaloid that can be extracted from the seeds of Peganum harmala L. Harmalol hydrochloride is the major metabolite of Harmaline and significantly inhibits dioxin-mediated induction of CYP1A1 at both transcriptional and post-translational levels. Harmalol hydrochloride showed vasorelaxant activity in isolated rat thoracic aortic preparations preconstricted with phenylephrine or KCl. Harmalol hydrochloride has antioxidant activity. |
| In vitro | 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.[1]Harmalol (25 μM) reduces glutamate-induced cytotoxicity, cytochrome c release, caspase-3 activation, and the production of reactive oxygen species (ROS) in PC12 cells.[2] |
| Target activity | H4 human glioblastoma:23.7 μM(IC50s), MAO-A:0.66 μM, DYRK1A:0.63 μM |
| Synonyms | Harmidol hydrochloride |
| molecular weight | 236.7 |
| Molecular formula | C12H13ClN2O |
| CAS | 6028-07-5 |
| Storage | store at low temperature | Powder: -20°C for 3 years | In solvent: -80°C for 1 year |
| Solubility | DMSO: 90.0 mg/mL (380.2 mM), Sonication is recommended. |
| References | 1. El Gendy MA, et al. Harmaline and harmalol inhibit the carcinogen-activating enzyme CYP1A1 via transcriptional and posttranslational mechanisms. Food Chem Toxicol. 2012;50(2):353-362. 2. Han E S, et al. Inhibition of Glutamate-Induced Change in Mitochondrial Membrane Permeability in PC12 cells by 1-Methylated β-carbolines. The Korean Society of Applied Pharmacology. 2003;11(2): 112-118. 3. Brierley DI, et al. Developments in harmine pharmacology--implications for ayahuasca use and drug-dependence treatment. Prog Neuropsychopharmacol Biol Psychiatry. 2012;39(2):263-272. 4. Tse SY, et al. Antioxidative properties of harmane and beta-carboline alkaloids. Biochem Pharmacol. 1991;42(3):459-46 5. Tarpley M, 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. 2021;162:105821. |