Physicochemical Properties
| Molecular Formula | C12H11CLN2 |
| Molecular Weight | 218.68 |
| CAS # | 21655-84-5 |
| Related CAS # | Harmane;486-84-0;Harmane-d4;2012598-89-7;Harmane (Standard);486-84-0 |
| SMILES | CC1=C2C(=CC=N1)C3=CC=CC=C3N2.Cl |
| Synonyms | Harman's alkali hydrochloride |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | hMAO-A 0.5 μM (IC50); MAO-B 5 μM (IC50); α2-adrenergic receptor 18 μM (IC50); I1-Imidazoline receptor 30 nM (IC50); nAChR 24 μM (IC50); benzodiazepine receptor 7 nM (IC50); Opioid receptor 2.8 μM (IC50); Loperamide 163 μM (IC50); Serotonin 101 μM (IC50) |
| ln Vitro | Harmane hydrochloride inhibits spironol and serotonin with IC50 of 163 μM and 101 μM, respectively [1]. Harmane hydrochloride has an IC50 of 7 μM for the benzodiazepine receptor flunitrazepam, 24 μM for the muscarinic acetylcholine receptor (QNB), 2.8 μM for the opioid receptor, and 42 μM for the opioid receptor in the presence of 50 mM sodium ions. The IC50 for spironol and serotonin are 163 and 101 μM respectively [1]. Harmane hydrochloride has an IC50 of 30 nM for I1-imidazoline receptors and 18 μM for α2-adrenergic receptors [2]. Harmane hydrochloride (1 μM) increased the mutagenicity of AAF to Salmonella typhimurium TA98 by three times in the presence of an S-9 mixture (containing 4 μM NADH and NADPH per ml but no NADP); in the absence of S-9, it increased the mutagenicity of N-acetoxy AAF by 2.5 times [4]. Harmane hydrochloride (5-25 μM, 0-72 h) reduced the dopamine content in PC12 cells (IC50 of 21.2 μM) in a concentration-dependent manner and could reduce the dopamine content induced by L-DOPA [6]. Harmane hydrochloride (20 μM, 0-72 h) inhibited the activity of tyrosine hydroxylase (TH) in PC12 cells at 24 h and restored it to normal levels at 72 h; it inhibited the expression of TH mRNA at 6 h and recovered it at 48 h [6]. Harmane hydrochloride (20 μM, 30 min) reduces the intracellular cyclic AMP level and intracellular calcium concentration in PC12 cells[6]. Harmane hydrochloride (80-150 μM, 24-48 h) exhibits cytotoxicity and induces cell death[6]. |
| ln Vivo | The ED50 of Harman (0-12.5 mg/kg, tail vein injection, single dose) in rats is 3.6 mg/kg, and the anticonvulsant effect lasts for a short time, delaying the reaction time to pain[1]. Harman (0.01-1 nM, injected into the rostral ventrolateral medulla, single dose) can cause a decrease in blood pressure in rats[2]. Harman (2.5-10 mg/kg, intraperitoneal injection) has anxiolytic and antidepressant effects in rats[5]. |
| Cell Assay |
Cell Cytotoxicity Assay [6] Cell Types: PC12 Tested Tested Concentrations: 80-150 μM; 20, 100, 150 μM Incubation Duration: 24, 48 h Experimental Results: Showed cytotoxicity, and cell apoptosis was observed after 48 h of treatment with 150 μM. Tested Tested Concentrationss higher than 150 μM could induce apoptotic cell death. Had stronger cell viability than L-DOPA alone. Real Time qPCR [6] Cell Types: PC12 Tested Tested Concentrations: 10-30 μM Incubation Duration: 0-72 h Experimental Results: Inhibited the increase in dopamine content induced by L-DOPA. Reduced dopamine content, tyrosine hydroxylase activity and mRNA at 6 h, which was maintained for 48 h and gradually recovered at 72 h. |
| Animal Protocol |
Animal/Disease Models: Female Wistar rats[1] Doses: 0, 3.125, 6.25 mg/kg, single dose; 0, 1.56, 3.125, 6 25, 12.5 mg/kg, single dose; 0, 1.56, 3.125, 6.25 mg/kg, single dose Route of Administration: Intravenous injection (i.v.) Experimental Results: Delayed apamorphine-induced licking. Increased body temperature in rats, reaching the highest value in 25 minutes. 3.125 mg/kg or above caused hypothermia in a dose-dependent manner. Body temperature returned to the control level 100 minutes after injection of 3.125 or 6.25 mg/kg. Prolonged the reaction time to nociception. At 3.125 mg/kg, a delay in reaction could be detected in 20 minutes. Animal/Disease Models: β-carbon alkali-induced hypotension in rats[2] Doses: 0.01-1 nM Route of Administration: Injection into RVLM (rostralventrolateral medulla) Experimental Results: Caused a dose-dependent decrease in mean arterial pressure (MAP) without significant changes in heart rate (HR). Phaloxan could reverse the decrease in MAP. Animal/Disease Models: Male adult Sprague-Dawley rats[5] Doses: 2.5, 5.0, 10 mg/kg Route of Administration: Intraperitoneal injection (i.p.) Experimental Results: Reduced the immobility time in the swimming test and increased the time in the open arms in the maze test dose-dependently. |
| References |
[1]. On the neuropharmacology of harmane and other beta-carbolines. Pharmacol Biochem Behav. 1981 May;14(5):693-9. [2]. Harmane produces hypotension following microinjection into the RVLM: possible role of I(1)-imidazoline receptors. Br J Pharmacol. 2000 Mar;129(6):1057-9. [3]. β-Carbolines as selective monoamine oxidase inhibitors:In vivo implicationshttps://pubmed.ncbi.nlm.nih.gov/7130973/. [4]. Harmane induces anxiolysis and antidepressant-like effects in rats. Ann N Y Acad Sci. 2005 Aug 9;65(3):391-6. [5]. Effects of harman and norharman on dopamine biosynthesis and L-DOPA-induced cytotoxicity in PC12 cells. Eur J Pharmacol. 2008 Jun 10;587(1-3):57-64. |
Solubility Data
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.5729 mL | 22.8645 mL | 45.7289 mL | |
| 5 mM | 0.9146 mL | 4.5729 mL | 9.1458 mL | |
| 10 mM | 0.4573 mL | 2.2864 mL | 4.5729 mL |